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Theo Epstein

Theo Epstein Steps Down As Cubs President Of Baseball Operations

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1:48PM: In a press conference this afternoon, Epstein told MLB.com’s Jordan Bastian and other reporters that he “won’t be paid in 2021, which is appropriate and the right thing.”  The salary was not a “primary” factor in his decision to resign but it was “part of the equation.”  As per the reported terms of Epstein’s last contract extension, he was set to make roughly $10MM in 2021.

11:04AM: Theo Epstein has stepped down as the Cubs’ president of baseball operations, as per a team announcement.  The move is effective as of November 20.  General manager Jed Hoyer will step into Epstein’s role.

Epstein issued the following statement:

“For the rest of my life, I will cherish having been part of the great Chicago Cubs organization during this historic period.  All of the things that have made this experience so special — the fans, the players, the managers and coaches, ownership, my front office colleagues, the uniqueness of the Wrigley experience, the history — make it so tough to leave the Cubs.  But I believe this is the right decision for me even if it’s a difficult one.  And now is the right time rather than a year from now.  The organization faces a number of decisions this winter that carry long-term consequences; those types of decisions are best made by someone who will be here for a long period rather than just one more year.  Jed has earned this opportunity and is absolutely the right person to take over this baseball operation at such an important time.”

“I am grateful to everyone with the Cubs: to the Ricketts family for this opportunity as well as for their loyalty; to the fans for their support and the depth of their emotional connection with the team; and to the players, coaches, staff and my front office colleagues for their friendship, excellence and dedication to helping us accomplish our initial goals of regular October baseball and a World Championship.”

There was widespread speculation that Epstein would leave the organization after the 2021 season, when his contract was up.  (Epstein himself is on record as saying that remaining in one job for too long a period isn’t necessarily beneficial to either the employee or the team.)  Today’s news jumpstarts that timeline and removes any lingering “lame duck” feeling over the Cubs’ decision-making process this offseason and throughout 2021.

Of course, the next round of speculation immediately turned towards whether or not Epstein could be turning towards another challenge — namely the open president of baseball ops positions with the Mets or Phillies.  According to MLB Network’s Jon Morosi, however, Epstein will not be immediately taking another job and will instead take 2021 off.  Epstein confirmed the same in a letter to friends, ESPN.com’s Jeff Passan reports, saying that “Next summer will be my first in 30 years not clocking into work every day at a major league ballpark.…I do plan on having a third chapter leading a baseball organization someday, though I do not expect it to be next year.”  Despite Epstein’s declaration, 670 The Score’s Bruce Levine tweets that the Phillies are still planning to “aggressively” pursue Epstein’s services.

Since joining the Cubs in October 2011, Epstein oversaw an extensive, multi-year rebuilding process that delivered the most sustained run of success at Wrigley Field in over a century.  Over the last six seasons, the Cubs have captured three NL Central titles, reached the postseason five times, and finally ended their World Series drought by capturing the championship in 2016.

Over nine seasons in Chicago and nine seasons as the Red Sox general manager, Epstein has long since booked his ticket into Cooperstown, with three World Series titles (and two broken curses) on his resume.  Epstein is still over a month away from his 47th birthday, so there is plenty of time for him to add further chapters to his already legendary career.  As The Athletic’s Ken Rosenthal and Jayson Stark wrote in a piece this morning, that next step could be a CEO role with a team rather than working as a president of baseball operations, perhaps looking “to form an ownership group with like-minded people and/or longtime associates, then attempt to purchase a club.”

Hoyer’s contract was also rumored to be up after the 2021 season, but he and the Cubs are putting the finishing touches on an extension, The Athletic’s Sahadev Sharma reports.  Hoyer has been one of Epstein’s chief lieutenants for a total of 17 seasons in both Boston and Chicago, and he also has past experience running a baseball ops department when he was the Padres’ general manager in 2010-11.

With the baton officially passed, Hoyer will now be in charge of what could be a transformative offseason in Wrigleyville.  As successful as the Cubs have been under Epstein, there is also some sense of underachievement, as the team hasn’t won a playoff series since 2017.  The core group of the 2016 championship team has gotten older, more expensive through arbitration and, in some cases, less effective on the field.

The Cubs now seem open to trading from this veteran core in order to both save payroll space in the wake of pandemic-lowered revenues and to perhaps spark something of a rebuild on the fly.  In the press release, both Hoyer and team chairman Tom Ricketts used the phrase “sustained success” to describe the Cubs’ next phase, and while this offseason’s moves will ultimately tell the tale, there isn’t yet any indication that the Cubs aren’t planning to contend in 2021.

Front Office/Coaching Notes: Red Sox, Venable, Marlins, Denbo, Cubs, Epstein, Hoyer

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The Red Sox are beginning the process of bringing in candidates for their managerial opening. Cubs coach Will Venable has already come in to interview, while George Lombard of the Dodgers and Don Kelly of the Pirates are likely on the list of incoming interviewees, per MLB Network’s Jon Heyman (via Twitter). Venable has been a popular managerial candidate recently. He interviewed for openings with the Astros and Giants last season, ultimately returning to the Cubs to serve as their third base coach in 2020. The former player moved back into the dugout for the 2018 season after being hired by the Cubs as a special assistant. For the Red Sox opening, however, Alex Cora continues to be seen as the favorite, though he will not be able to interview for the role until his suspension lifts after the conclusion of the World Series.

  • The Marlins are looking to hire a Team President that can complete their upper leadership group in the player ops department. That means augmenting and supplementing the work of Gary Denbo, their Director of Player Development and Scouting. Derek Jeter and Denbo are close, making it easy to presume that he could be a candidate to fill Michael Hill’s Team President role, but that’s not the case, per Barry Jackson of the Miami Herald. Jackson provides a quote from Jeter that shines some light on his thinking for the position, as Jeter said, “Gary has done a great job where he is right now. You look at how you build an organization; you have to have a great scouting department and a great player development department. Gary deserves a lot of credit for what we’ve been able to do to this point. Where he is right now is where he is most important.”
  • The Cubs and Theo Epstein remain aligned on the current plan for Epstein to play out the last year of his contract before likely departing after 2021. Executive VP and General Manager Jed Hoyer does not share Theo’s exit strategy, however, and it seems right now as if he’ll stay on to fully take control of the Cubs’ baseball ops department after Theo departs, writes The Athletic’s Sahadev Sharma and Patrick Mooney. Hoyer has served as Theo’s partner in the front office for many years, but Theo still steers the ship, as was the case specifically with the Cubs’ rigorous approach to COVID-19 testing this year when they were the only team in the majors without a positive test. Hoyer will preserve a healthy dose of continuity when Theo leaves, but there will be change when the buck officially stops with him.

Theo Epstein On The Value Of One-Year Deals

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Theo Epstein has been prepping the Chicago fanbase for the eventual breakup of their 2016 team for a couple of seasons now. The blockbuster hasn’t come, and most of the faces of that championship team remain. After a disappointing exit from the wild card round – they managed just one run over a two-game sweep at the hands of the Marlins – Epstein’s comments again suggest changes are coming for the Cubbies.

Nine players remain on the roster from their World Series winner, and while that may not seem like a lot, it does constitute roughly 35% of a 26-man roster. Kris Bryant, Anthony Rizzo, Javier Baez, Willson Contreras, Albert Almora, Jon Lester, Kyle Hendricks, Jason Heyward, and Kyle Schwarber represent the longest-tenured group of Chicago players. Technically, manager David Ross can count as a 10th member of their title team still hanging around the clubhouse. Ian Happ and Victor Caratini didn’t debut until 2017. Jose Quintana joined the team at the 2017 deadline. Yu Darvish signed as a free agent prior to the 2018 season.

The pillars of this Cubs’ run will dwindle further in the coming years. Architect Theo Epstein is likely to depart after next season. Lester is a free agent this winter. Almora seems to be out of chances and in need of a change of scenery. Odds favor Heyward or Hendricks to be the “last man standing” as they both have contracts that should keep them in Wrigley through 2023. Rizzo, Bryant, Baez, and Schwarber are each entering the final year of their contracts – assuming the Cubs pick up Rizzo’s $16.5MM option.

Epstein spoke about the latter group, providing typically candid analysis of not only the Cubs foursome, but more broadly about the value of one-year contracts. Per the Athletic’s Sahadev Sharma, Epstein said:

I think there are going to be certain fundamentals that are true of this winter and of this market that have been true for decades. One of those is especially relevant in our situation, a one-year deal for a really talented player is a valuable thing. That’s to our benefit both to what we can do in constructing the 2021 team and having an additional year of control on certain players and also potentially to our benefit in the trade market as we look to make some changes. I think that’s a fundamental.”

Essentially, it sounds as if Epstein’s offering a ’fear not’ for those who think the Cubs have waited too long to return anything of value for the final year of Bryant, Rizzo, Baez, and/or Schwarber. To Epstein’s point, players on one-year deals are often devalued in the public square, but there’s a lot that can be extracted from a full year. Further, the flexibility a one-year deal affords shouldn’t be discounted – perhaps especially in our current climate. The fear of losing talent to free agency is understandable, but the more difficult gaff to overcome is the presence of “the albatross,” a highly-paid player on a long-term deal who no longer contributes on the diamond. Baez’s confounding 2020 is a testament to the swings that even talented players can experience year-over-year.

The trouble for Epstein is that Chicago’s current roster is flush with semi-expensive players on short-term deals who are coming off disappointing seasons. But to Epstein’s point – those players are still valuable. Whether the Cubs keep them or trade them, there’s always an opportunity cost. Said Epstein, per Sahadev:

There’s always a trade-off of being transactional and taking some of those players away from the current group and solidifying the future. There are trade-offs and balances that you have to be mindful of. The math simply changes as you get to a point where a lot of your best players only have one year left. It becomes less appealing to continue to invest opportunity cost in simply the present.”

Epstein has hit on a similar refrain in each of the last couple of years, and some changes have been made. They hired David Ross as the manager, they refrained from big-money free agent deals since signing Darvish (with the exception of Craig Kimbrel, who has only one more guaranteed season left on his deal), and they poured considerable energy into exploring trade options and/or extensions for their stars – but they haven’t made any of those deals.

Therein lies the rub for Epstein and GM Jed Hoyer. After years of exploring their options and walking the difficult path to try and sustain contention, they’re running out of time to pull off one of those – in Epstein’s words – “impactful, significant moves.” Whether or not they’re able to consummate that brand of deal this winter may depend on whether the 29 other GMs agree with Epstein about the value of talented players one-year deals.

Of course, Mookie Betts represents the most recent superstar player to be dealt on a one-year deal, and Indians’ shortstop Francisco Lindor is among those players who could be available this winter. Both players are probably more valuable in a vacuum than any of the Cubs’ foursome. Still, the Betts deal is instructive in so far as it necessitated the Red Sox’ willingness to take a step back, even though they received a major league regular as part of their return. The Cubs also have the option of packaging a couple players in the same deal, something he’s done in the past to extract additional prospect value..

Theo Epstein Discusses Cubs’ Future

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The Cubs’ season came to an abrupt end last week, when the Marlins swept the NL Central winners in the teams’ first-round series. Despite generally strong regular-season play, the North Siders have now failed to advance to a National League Division Series in each of the past three seasons. President of baseball operations Theo Epstein discussed the organization’s outlook in an end-of-season chat with reporters this morning.

Having not quite lived up to lofty expectations in recent years, Epstein acknowledged some change this offseason “is warranted and necessary” (via Russell Dorsey of the Chicago Tribune). There’s seeming room for improvement on both sides of the ball. On the whole, Cubs’ hitters slashed just .220/.318/.387, resulting in a 91 wRC+ that ranked 21st out of the league’s 30 teams. Among everyday players, only Ian Happ and Jason Heyward performed up to or exceeded expectations. Anthony Rizzo was decent but didn’t play at his established levels, while Kris Bryant and Javier Báez scuffled through miserable seasons.

On the pitching side, Yu Darvish again cemented himself as a bona fide ace, with Kyle Hendricks continuing to shine as the #2 option. The rest of the rotation is uncertain, with José Quintana, Jon Lester and Tyler Chatwood all ticketed for free agency. 25-year-old Adbert Alzolay has the inside track on a rotation spot, Epstein confirmed (via Mark Gonzales of the Chicago Tribune), but he admitted the front office will have to look outside the organization for additional pitching help. Whether the Cubs could make any high-priced additions isn’t clear, as Epstein said the franchise is facing a high amount of financial uncertainty in the wake of the COVID-19 pandemic (Gonzales link), as is more or less true of all 30 clubs.

Being open to some changes on the roster is hardly the same as desiring massive turnover; GM Jed Hoyer made similar comments last November, but the organization had a generally quiet 2019-20 offseason. The existing core is clearly capable of making another run in the NL Central, assuming the pitching staff is bolstered in some fashion. It remains to be seen if the conditions for a more drastic shakeup present themselves.

The 46-year-old Epstein also addressed his personal future. His contract expires after the 2021 season, and he’s reportedly planning to meet one-on-one with chairman Tom Ricketts in the coming days. Epstein confirmed he’ll sit down with ownership but downplayed the meeting’s significance, calling it a customary end-of-year process. “My expectation is that I’ll be here (next season),” he told reporters (including Jordan Bastian of MLB.com).

That said, Epstein hinted at the possibility that 2021 could be his final year in Chicago. When asked about the prospect of an extension, he noted that changes after a long time spent in one place could be beneficial for both employees and the organization (via Gonzales). As Jesse Rogers of ESPN.com points out (Twitter link), that’s in line with an increasing expectation Epstein might depart at the end of his deal.

If that were to happen, Hoyer would seem an obvious candidate to take over baseball operations. Long-term front office uncertainty aside, Epstein says he’s currently “as invested in the Chicago Cubs as I was at any point in the last nine years,” (Rogers link).

NL Notes: Mets, Cubs, Theo

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We’ve already covered a handful of National League notes today. Here’s more from the Senior Circuit.

  • Like most teams, the Mets imposed pay cuts for many employees this summer in response to pandemic-driven revenue losses. However, Mets employees will receive their full salaries from November 1 onward, per Tim Healey of Newsday. Likely incoming owner Steve Cohen drove that decision. Cohen’s still awaiting formal approval from 23 of the league’s 30 owners (which he’s expected to get) before his reported $2.475 billion purchase of 95% of the franchise becomes official. He’s permitted to consult on organizational decision-making in the interim, Healey notes.
  • The Mets’ forthcoming sale also figures to bring substantial changes in personnel. Cohen has already confirmed plans to hire Sandy Alderson as team president if and when he formally takes the reins. A few potential staffers Cohen and Alderson could pursue for various roles this offseason (via Andy Martino of SNY): Nationals assistant hitting coach Pat Roessler, Athletics assistant general manager Billy Owens, and Rays special assistant Bobby Heck. Roessler was on the Mets’ coaching staff from 2015-18, overlapping with Alderson’s time as the franchise’s general manager. Owens, meanwhile, has been in the Oakland front office for nearly two decades and reportedly drew some consideration last offseason for the Giants’ GM job, which eventually went to Scott Harris.
  • On the heels of an early playoff exit, Cubs president of baseball operations Theo Epstein plans to meet with chairman Tom Ricketts next week to discuss the club’s long-term future, per David Kaplan of NBC Sports Chicago. Epstein’s contract expires after the 2021 season, and Kaplan points out the possibility he could turn over baseball operations to general manager Jed Hoyer and look for opportunities elsewhere once his deal wraps up. Per Patrick Mooney of the Athletic, though, Epstein isn’t expected to depart the organization this winter.

Cubs Notes: Epstein, Extensions, Catchers

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Theo Epstein has largely led his clubs with positive, progressive messaging that, if anything, lands on the overly-diplomatic end of the spectrum. True to form, he and the Chicago Cubs organization are encouraging their players to speak their minds as they so choose, writes Tim Stebbins of NBC Sports. Though Epstein’s comments may come off as hollow, there’s little to suggest he’s being anything but sincere. He’s been up front about wanting to organizationally (and personally) take a long, inward look at themselves for traces of the systemic racism that’s been at the fore of the country’s cultural conversation. These comments stemmed from a tweet from Adbert Alzolay that voiced some of his concerns about camp in South Bend. That tweet, however, was deleted after some of his facts proved to be inaccurate, per The Athletic’s Sahadev Sharma. This Here’s more from Chicago…

  • Epstein more-or-less put the kibosh on any potential extensions for Chicago’s many popular, star players, per MLB.com’s Jordan Bastian. After Kris Bryant recently re-iterated his desire to stay in Chicago, it’s a little disquieting to hear Epstein so thoroughly shut down the idea of extending much-beloved Cubs like Bryant, Javier Baez, or Willson Contreras. On the other hand, it’s certainly a confusing time in baseball, and there are plenty of logistics to keep the organization busy just in trying to keep players safe and return to the game of baseball. The market for star players like Bryant and Baez could not be any more uncertain, and with at least two seasons before any of their core players reach free agency, the Cubs have the luxury of time. If nothing else, next offseason will offer a fascinating data point as Mookie Betts hits the open market. The Cubs certainly have the funds to re-up their stars, but they might just want to wait to see the going rate for a superstar in these uncertain times.
  • On the field, manager David Ross is mulling the possibility of carrying three catchers once the season starts, per Bastian (via Twitter). Given the somewhat chaotic terms of the 2020 season, it would not be surprising to see many teams go this route. For the Cubs specifically, Victor Caratini proved enough with the bat last season to get some at-bats at first base or designated hitter while Contreras continues to serve as the everyday catcher. The switch-hitting Caratini, 26, hit .266/.348/.447 across 279 plate appearances. He saw 23 starts at first base and 2 at third base to go along with 59 starts behind the plate. Josh Phegley would figure to be the third catcher. Phegley hasn’t rated all that well defensively, but the former Oakland Athletic did pop 12 homers with a .411 slugging percentage last season.

Angels Notes: Maddon, Cubs, Anderson, Pena, Soriano

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Joe Maddon is pleased to be returning to the Angels organization as the team’s new manager, the veteran skipper tells ESPN.com’s Alden Gonzalez.  Rumors about Maddon taking over the managerial post swirled for much of last season, and the Angels ended up being the only team Maddon officially interviewed with, after a dinner with owner Arte Moreno, team president John Carpino and GM Billy Eppler.  “I just thought it would’ve been disingenuous to accept interviews with anyone else if I truly wanted to be here.  And then, after it was all set and done, it couldn’t have been more obvious it was the right thing to do for me,” Maddon said.

Maddon also touched on his departure from Chicago, telling Gonzalez that he decided during the 2019 season that he was ready to move on from the team.  There was heavy speculation that the Cubs were planning a managerial change when no extension talks were held with Maddon prior to his last year under contract, and Maddon said some “philosophical differences” emerged following what was perceived as a disappointing 2018 season.  The front office “wanted to control more of what was occurring in just about everything,” Maddon said, as “when I started there — ’15, ’16, ’17 — it was pretty much my methods. And then all of a sudden, after ’18 going into ’19, they wanted to change everything.”

Interestingly, Cubs president of baseball operations Theo Epstein provided something of a counterpoint to Maddon’s statement, telling The Athletic’s Sahadev Sharma that he didn’t feel any “philosophical differences” existed with Maddon.  Epstein didn’t entirely deny that the front office played a larger role in 2019, as while he didn’t see the extra attention as overly controlling, he felt he had to address what he saw as a “growing organizational complacency” in the clubhouse.  “I think his [Maddon’s] approach was more that things will work themselves out.  These are great players, let them play and these things will work out,” Epstein said.  “From my perspective, there was a little bit more cause for concern.  It wasn’t an everyday thing that I would try to step in and offer feedback, help and remind about expectations.”

Some more out of Anaheim…

  • Right-hander Justin Anderson will be out for four-to-six weeks and will begin the season on the injured list, Maddon told MLB.com’s Rhett Bollinger and other reporters.  Anderson suffered a Grade 2 strain in his left oblique while playing catch on Tuesday.  The 27-year-old is entering his third season in Los Angeles and looking to improve on an injury-hampered 2019 that saw Anderson post a 5.55 ERA over 47 relief innings, while battling a trapezoid issue.
  • Maddon also provided an update (to the Athletic’s Fabian Ardaya and other reporters) on right-hander Felix Pena, who is expected to be ready for Opening Day.  Pena tore his right ACL last August and had a projected recovery time of six-to-nine months, though it seems as if Pena is progressing well and won’t require the long end of that projection.  Pena has a 4.38 ERA, 8.9 K/9, and 3.00 K/BB rate over 189 innings since the Angels acquired him in a deal with the Cubs during the 2017-18 offseason, with Pena starting 24 of his 41 games as a semi-regular rotation fill-in for the Halos’ many pitching injuries.  Most notably, Pena tossed the final seven innings of the Angels’ combined no-hitter on July 12, entering the game as the bulk pitcher after opener Taylor Cole.
  • Angels pitching prospect Jose Soriano will miss the entire 2020 season after undergoing Tommy John surgery, MLB.com’s Jonathan Mayo reports (Twitter link).  At the end of last season, MLB Pipeline ranked the right-hander as the ninth-best minor leaguer in the Angels’ farm system, praising Soriano’s “electric fastball” that sits in the 97-98mph range and a breaking ball that “trends towards being a plus pitch.”  The 21-year-old Soriano is coming off a solid season spent mostly at A-ball Burlington, posting a 2.55 ERA, 9.7 K/9, and 1.75 K/BB rate over 77 2/3 innings (starting 15 of 17 games).

Grading Theo Epstein’s Cubs Free Agent Signings

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Theo Epstein has served as the Cubs’ President of Baseball Operations for nine offseasons now.  With an eye on contending beginning in 2015, the club committed at least $191MM in three of four offseasons.  The Cubs were able to avoid paying the luxury tax in 2018, resetting their penalty percentages for 2019.  Under the designation of a first-time payor, the club received a $7.6MM luxury tax bill for ’19.  For 2020, it appears Cubs ownership under the Ricketts family is again treating the base tax threshold – $208MM for 2020 – as something of a salary cap.  Based on the team’s quiet offseason, it appears that the Ricketts aren’t willing to go much beyond that point.

Had the Cubs brushed up against the second surcharge threshold of $248MM, they would have been subject to a tax bill in the neighborhood of $14MM, and could have potentially reset in 2021 with Jon Lester, Jose Quintana, and Tyler Chatwood coming off the books.  Given that relatively modest one-time penalty, the question must be asked: is there more at play in the Ricketts’ unwillingness to spend?  For example, could ownership’s reluctance to spend be a function of Epstein’s track record in free agency?  In other words, can the Cubs’ top exec be trusted with the checkbook?

To answer that question, I’ve assigned a letter grade to each of Epstein’s 15 Cubs free agent signings of $10MM or more.  Aside from the grades, this will also provide context on how the Cubs got to their present situation.  Note that this analysis omits some effective bargain contracts, such as the Cubs’ 2012 signing of pitcher Scott Feldman.  That signing netted the Cubs Jake Arrieta and Pedro Strop in a trade months later, which turned out to be a masterstroke.  Still, that’s more a testament to Epstein’s trading ability than a measure of his track record in signing significant free agents.

The Rebuilding Years

David DeJesus – signed on 11/30/11 for two years, $10MM.  Grade: B

What we said at the time: Given the lack of offense he provided the Athletics, DeJesus didn’t come at a bargain price for the Cubs. Still, the 32-year-old will be worth the money if he bounces back in his first extended National League exposure. 

DeJesus was Epstein’s first free agent signing of his Cubs tenure.  This signing worked out fine.  At the time, the Cubs were still running out the clock on left fielder Alfonso Soriano’s deal, while they had little to speak of in right or center field.  DeJesus wound up leading the team in defensive innings at both of those positions in 2012, and served as a classic second-division regular.  In August of the second year of DeJesus’ contract, the Cubs essentially gave him away to the Nationals to avoid paying his remaining $2.5MM.

Edwin Jackson – signed on 12/20/12 for four years, $52MM.  Grade: F

What we said at the time: They paid about market value for Jackson, which could net a profit if he improves. The contract will make more sense to me if the Cubs aim to contend in 2014. Otherwise, they won’t get a lot out of the first half of the contract, when Jackson is closest to his prime. A contract of this nature might have been a better move during the 2013-14 offseason, when the team will be presumably closer to winning.

Jackson was Epstein’s first major free agent signing for the Cubs, and at the time the move had a “this money is burning a hole in our pocket” vibe.  The Cubs had run parallel pursuits of the second and third-best free agent starters that winter, Jackson and Anibal Sanchez.  You probably don’t remember it this way because Sanchez’s deal ended poorly, but his first two seasons of that five-year, $80MM deal with the Tigers were good enough to pay for almost the entire contract.

Jackson’s selling point was taking the ball every fifth day and putting up an ERA around 4.00, perhaps with a little bit of upside to unlock.  Cubs GM Jed Hoyer said at the time, “He pitched all of last year at 28 years old, he’s been incredibly durable, had some really excellent seasons during his time in the big leagues, and we actually think his best days are ahead of him.”  That position was a reasonable one, although Jackson still seemed unnecessary for a team with two rebuilding seasons ahead of it.  More sensible were the Cubs’ smaller rotation depth deals that winter, for Scott Feldman, Scott Baker, and Carlos Villanueva.

Ultimately, Jackson bombed in Chicago, making 58 starts with a 5.58 ERA over the first two seasons.  By June of the third year, the righty was released.  The lesson, perhaps, was not to spend significant money on non-star free agents.   

Carlos Villanueva – signed on 12/20/12 for two years, $10MM.  Grade: B

What we said at the time: He’ll be a useful swingman.

Villanueva was indeed able to serve as a useful swingman for the 2013-14 Cubs, providing 20 starts due to a Matt Garza injury and the Feldman, Jeff Samardzija/Jason Hammel trades.  But it wasn’t hard to move him back to the bullpen when the Cubs needed a spot for Arrieta.

There’s a gap here, as the Cubs had a quiet 2013-14 offseason.  It wasn’t for lack of trying, however, as they made a $120MM bid for Masahiro Tanaka.

Creating a Winner

Jason Hammel – signed on 12/12/14 for two years, $20MM.  Grade: B

What we said at the time: Signing Hammel would help them stabilize the middle of their rotation, but presumably would not preclude them from continuing to pursue an ace like Lester. The reported terms make for an attractive price for Chicago.

The Cubs had included Hammel with Samardzija in the trade that netted them Addison Russell from Oakland in the summer of 2014, and then they brought Hammel back as a free agent in December.  The team was able to avoid a three-year commitment and add a secondary rotation piece as Epstein made his first real push for contention.  Though Hammel failed to make an impact in the playoffs in his time with the Cubs, he provided solid regular season work with a 3.79 ERA across 61 regular season starts.

Jon Lester – signed on 12/13/14 for six years, $155MM.  Grade: A

What we said at the time: The lofty $155MM price tag matched expectations, and after years of conserving payroll, the Cubs can certainly afford it. The Cubs need their new ace to be a workhorse, a trait that’s missing from the team’s other projected starters. Any deal of this magnitude and length for a starting pitcher carries a lot of risk, but the Lester signing addressed the team’s biggest need without sacrificing young cornerstone players or a draft pick.

The Cubs put a monumental effort into their pursuit of Lester, convincing him that the team was ready to contend.  His signing marked a turning point for the franchise.  Lester delivered, especially on the front end of the deal with 9.1 WAR in the first two seasons and 35 2/3 superb, crucial frames in their 2016 postseason run.  The Cubs don’t win the World Series without Lester, cementing his status as a franchise legend.  Even as Lester transitions into more of a back-rotation arm, he’s continued to provide the Cubs with solid innings, meaning the Cubs will likely get an even-money return on their investment.

The Cubs signed Lester in the 2014-15 offseason, and also pursued free agents Russell Martin and James Shields that winter.  After the 2015 club surprisingly reached the NLCS, the Cubs pushed in more chips on their heaviest-spending offseason to date.

John Lackey – signed on 12/4/15 for two years, $32MM.  Grade: B

What we said at the time: I thought Lackey would command a three-year deal even at his advanced age and with a qualifying offer attached, so plucking him from the Cardinals on a two-year term was a big win. 

After entering the offseason seeking impact starting pitching, the Cubs finished a “distant third” to the Red Sox in the bidding for David Price, according to Epstein.  That led him to a much more modest commitment with Lackey.  Lackey’s tenure with the Cubs was similar to that of Hammel: good value in his first season with the team, and minimal postseason impact.

Ben Zobrist – signed on 12/8/15 for four years, $56MM.  Grade: A

What we said at the time: I was surprised by the Cubs’ plan to move Castro to make room for a second baseman from outside the organization. Instead of plugging Baez in at second base, the Cubs went with veteran Ben Zobrist, who turns 35 in May. Zobrist served as Joe Maddon’s Swiss Army knife for six seasons after establishing himself in the Majors with the Rays. While Zobrist may not be the defensive asset he once was, he’s still an excellent high-contact hitter and potential three-win player. The Cubs should get good value with Zobrist at $14MM a year, despite the riskiness of signing a player through age 38. He’s a clear improvement over Castro, and with the Yankees taking on Castro’s contract, two-thirds of Zobrist’s deal is covered.

Like Lester, Zobrist became an integral part of the Cubs’ 2016 championship team, winning World Series MVP.  The distribution of his regular season value to the Cubs was uneven, with two seasons of around 4 WAR and two that were close to zero.  Ultimately, Zobrist gave the Cubs much more than $56MM worth of value.

Jason Heyward – signed on 12/11/2015 for eight years, $184MM.  Grade: D

What we said at the time: I was surprised to see the Cubs aggressively pursuing Jason Heyward, because right field didn’t seem like a primary need for the club. Nonetheless, they signed the offseason’s best position player to an eight-year deal guaranteeing $184MM. That the Cubs will effectively be signing Heyward away from the Cardinals only sweetens the deal for the club. Including an opt-out clause was a prerequisite to signing Heyward, who was an unusually young free agent at 26 years old. Now that the Cubs have Heyward and this contract, they have to hope he does opt out after 2018, making this a three-year, $78MM deal. If Heyward’s 2018 season is good enough to compel him to opt out (to which Matt Swartz assigns a 50% likelihood), then it likely means the Cubs got more than their money’s worth.

The best available free agent that winter – David Price – matched the Cubs’ desire for an impact starting pitcher.  Once Price signed with the Red Sox, the Cubs pivoted to the second-best available free agent in Heyward, much like the Angels signing Anthony Rendon after missing out on Gerrit Cole this winter.  The plan was for Heyward to serve as the Cubs’ center fielder, a position he had rarely played in the past but was thought to be able to handle due to his stellar right field defense.

Defense and baserunning made up a large part of Heyward’s value, but he was still a 116 wRC+ hitter over the three previous seasons.  Heyward was, in essence, a younger version of Carl Crawford: a low-power corner outfielder known for great defense and baserunning and a decent bat.  Crawford, signed by Epstein in Boston five years prior, became an epic bust.  Halfway through Heyward’s contract with the Cubs, the results have been similarly disappointing.  Heyward has managed to climb his way up to league average offense in the past two seasons, resulting in a pair of 2 WAR campaigns.  It’s not nearly enough for a player earning $23MM a year.  Barring a return to form, Heyward’s contract could wind up more than $100MM underwater for the Cubs.

A Cubs fan might be inclined to say, “Hey, it’s not my money, and you can’t put a dollar value on the rousing speech Heyward delivered in Cleveland during the rain delay of Game 7 of the World Series.”  Those things are true.  We can’t know whether Kyle Schwarber, Ben Zobrist, and Miguel Montero would have gotten those hits without the speech or if Carl Edwards and Mike Montgomery would have held onto the lead in the bottom of the inning.  But we do know that Heyward has failed to live up to his contract on the field, and that he’s a large part of the payroll crunch that has kept the Cubs from improving the team the past two winters.  Long thought to be of interest to the Cubs, Bryce Harper inked a contract with the Phillies with an average annual value only $2MM beyond that of Heyward.

Dexter Fowler – signed on 2/25/16 for one year, $13MM.  Grade: A

What we said at the time: Fowler’s talks with the Orioles fell apart when they wouldn’t give him an opt-out clause, and the Cubs swooped in with a low-risk one-year deal. While it’s true the Cubs sacrificed another potential draft pick, Fowler basically fell into their laps.

From a team perspective, when a low-risk free agent opportunity comes along, even after Spring Training starts, the payoff can be huge if you can find a few coins in the couch cushions and snag the player.  The Cubs had all but moved on from Fowler, but when he became available for one year and $13MM, they found the money and moved Heyward back to his natural position.  The unexpected contract became critical to the Cubs’ 2016 championship, as Fowler put up 4.6 WAR in the regular season and led off Game 7 of the World Series with a home run.

Attempting To Add Pitching

Tyler Chatwood – signed on 12/7/17 for three years, $38MM.  Grade: D-

What we said at the time: After coming up short on returning expat Miles Mikolas, the Cubs signed former Rockie Tyler Chatwood to a surprisingly large contract for a pitcher coming off a 4.69 ERA. Now that he’s out of Colorado, Chatwood has several things going for him: his age (28), his ability to induce groundballs, and a fastball approaching 95 miles per hour. Though it was surprising to see Chatwood land at nearly $13MM a year, he’s a solid upside choice to replace Lackey.

The Cubs were unwilling to go beyond $15.5MM for Mikolas – who ended up having a spectacular 2018 season – and instead set the market for Chatwood.  You might be noticing a trend here: when Epstein has won the bidding for a youthful free agent the Cubs perceive to have upside – Edwin Jackson, Jason Heyward, and Tyler Chatwood – the contracts have gone terribly.  Chatwood’s longstanding problem with the Rockies had been a lack of control, and the Cubs weren’t able to fix that.  In fact, in 2018, Chatwood walked nearly 20% of batters faced, by far the worst in the game among those with 100 innings.  Chatwood’s contract seems likely to land him the Cubs’ fifth starter job out of camp in 2020.  It’s another case of the Ricketts’ recent fiscal conservatism preventing the team from making upgrades – obviously the free agent and trade markets offered better alternatives for the Cubs’ rotation this winter.

Brandon Morrow – signed on 12/10/17 for two years, $21MM.  Grade: D-

What we said at the time: While his contract is reasonable, the risk comes in the Cubs’ reliance upon a pitcher with Morrow’s lengthy injury history and heavy 2017 postseason workload. Given the volatility of relievers, the contract itself is no riskier than those given to Wade Davis, Mike Minor, Jake McGee, Bryan Shaw, Tommy Hunter, Juan Nicasio, and others.

In 2017, Morrow emerged from a minor league deal and a long injury history to serve a key role in the Dodgers’ World Series run.  Though he may have been burned out pitching 13 2/3 postseason innings, Morrow’s only real blemish was a four-run drubbing in Houston at the hands of George Springer, Alex Bregman, Jose Altuve, and Carlos Correa that cost the Dodgers Game 5 of the World Series.  HMMMM.

It wasn’t trash can banging that did Morrow in with the Cubs, however.  He made it only to mid-July of the contract’s first season and hasn’t appeared in the Majors since due to injuries, though Morrow is currently healthy and in camp with the Cubs on a minor league deal.  To be fair, the 2017-18 offseason is so littered with free agent reliever busts that it’s difficult to say Epstein should have known better and signed, say, Craig Stammen.

Drew Smyly – signed on 12/12/17 for two years, $10MM.  Grade: D

What we said at the time: The Cubs quietly made a different free agent signing with a Maddon/Hickey connection, lefty Drew Smyly. Smyly had undergone Tommy John surgery in June of 2017, and was signed with an eye toward the 2019 rotation. If Smyly returns to full health and ability for 2019, the Cubs will have a good kind of problem on their hands in that they’ll have six established starting pitchers under control for that season.  

Though it’s only been two years, the Cubs seem far removed from a time when they would throw $10MM at a pitcher in hopes that he could provide depth a full season into the future.  Smyly was a luxury and a depth stash, and while he did return to a Major League mound in 2019, it wasn’t for the Cubs.  In the first omen of the club’s clamping down on payroll, Smyly was shipped to the Rangers as a pure salary dump so that the Cubs could “afford” Cole Hamels’ club option.  That the Cubs unloaded $7MM of Smyly’s contract and he was subsequently terrible for most of 2019 saves this from an F grade, but it’s hard to say whether Epstein got lucky or actually expected the lefty to struggle.

Steve Cishek – signed on 12/14/17 for two years, $13MM.  Grade: B

What we said at the time: Cishek, 31, has had a few ups and downs at times in recent years and has played with four organizations in the past three seasons. For the most part, though, he has continued to function as a quality setup option. The sidearming Cishek will offer a different look out of a re-worked Cubs pen.

It’s hard to complain about the results the Cubs got out of Cishek, who posted a 2.55 ERA across 134 1/3 innings in his two seasons.  Though he was generous with free passes, hitters generally couldn’t square him up.

Yu Darvish – signed on 2/10/18 for six years, $126MM.  Grade: C

What we said at the time: Darvish’s $21MM average annual value was surprisingly low. Like other big market teams, the Cubs are intent on staying below the $197MM competitive balance tax threshold, and the sixth year given to Darvish helped accomplish that. With Darvish in the fold alongside Jon Lester, Jose Quintana, Kyle Hendricks and Tyler Chatwood, the reigning NL Central champs will have one of the more complete (and formidable) rotations in all of baseball. 

Darvish’s debut season with the Cubs in 2018 was a disaster, as he made only eight starts due to injuries.  At that point, his contract looked like quite the albatross.  Even as late as July 3rd of the 2019 season, the righty’s ERA sat at 5.01.  Then, he reeled off a 13-start run with a 2.76 ERA, 118 strikeouts, and a mere seven walks in 81 2/3 innings.  A pitcher who had exhibited lousy control for the Cubs suddenly had the best control in baseball.  Darvish’s turnaround and the potential for strong work in the final four years of his contract means this contract could become a win for the Cubs.  Of course, Darvish is 33 now, so it could easily go south as well.

Craig Kimbrel – signed on 6/5/19 for three years, $43MM.  Grade: F

What we said at the time: With a career 1.91 ERA, 14.7 K/9, and 4.23 K/BB rate over nine seasons and 532 2/3 career innings, Kimbrel’s resume could very well eventually land him in Cooperstown down the road. While 2018 wasn’t as dominant as some of his past years, Kimbrel still seemed to have a viable platform year with a 2.74 ERA, 13.86 K/9, and 3.10 K/BB over 62 1/3 frames for the World Series-champion Red Sox.  Beyond the surface numbers, however, there were some red flags. It was hard to ignore Kimbrel’s increased struggles in the second half of last season, and then through Boston’s playoff run. 

It could be a win-win situation for Chicago, as the team looks to both avoid the top tax threshold while also getting a closer to bolster a bullpen that has generally been around the middle of the pack this season. The looming question could concern Kimbrel’s effectiveness, as other players whose qualifying offer-induced long waits in free agency (Stephen Drew and Kendrys Morales in 2014) both struggled badly after sitting out months of the season.

That concern from MLBTR’s Mark Polishuk proved prescient, as Kimbrel posted a 6.53 ERA while allowing nine home runs, more than a hit per inning, and a 12.5 BB% in his 20 2/3 innings.  Kimbrel has two more seasons with the Cubs to turn the contract around, with the possibility of an additional season vesting.  You can see how one bad signing begat another.  Morrow was unable to serve as the team’s closer in 2019 as planned, pushing the Cubs to use the money they saved from Ben Zobrist’s leave of absence on Kimbrel.  Now, due to Kimbrel’s presence and contract, the biggest addition to a questionable bullpen this winter was Jeremy Jeffress.

Of these 15 free agent contracts, Darvish, Heyward, Lester, Kimbrel, and Chatwood remain on the books for 2020.  For luxury tax purposes, that’s just under $97MM.  Epstein was able to win a World Series in Chicago in part due to free agent contracts for Lester, Zobrist, Fowler, and Lackey, but missteps on other players have led to the Ricketts family turning off the spigot – perhaps even at the expense of contention.

NL Notes: Dodgers, Cubs, Giants

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The Mookie Betts trade is in the books, but now that Joc Pederson is no longer headed to the Angels, the Dodgers will have to sort out their 40-man roster, tweets Bill Plunkett of the Orange County Register. The Dodgers have 42 players on their 40-man roster at present. Finding a new trade partner for Pederson and/or Ross Stripling might be the most obvious answer, but the Dodgers may prefer not to rush a transaction of that magnitude. Speculatively speaking, Tyler White could find himself on the chopping block, with Kyle Garlick, Zach McKinstry and Edwin Rios other non-established big leaguers whom the Dodgers may need to consider moving or exposing to waivers. While we wait for the final confirmation of this deal to go through, let’s check in elsewhere around the National League…

  • Theo Epstein saw the writing was on the wall long before the Cubs’ current financial strictures so severely limited their transactional flexibility, per Gordon Wittenmyer of the Chicago Sun Times. Epstein references a pattern – the Cubs, Astros, Red Sox – of teams reckoning with their young stars graduating into the arbitration process. After years of supporting homegrown cores with free agent additions in efforts to win a World Series, the Red Sox, Astros and Cubs, for differing reasons, have entered new phases. Sure enough, the Astros had to let Gerrit Cole walk in free agency, the Red Sox just shipped Mookie Betts to the Dodgers, and the Cubs are said to have been shopping Kris Bryant for most of the winter. Of course, the Cubs haven’t yet moved their young stars, but their value has declined. Epstein and company are stuck choosing between trading the stars from the cursebreaking Cubs at lower than peak value and watching them depreciate into a mediocre ballclub. Of course, there’s always the possibility of a bounceback for this Cubs core, but even a return to prominence in the NL Central would not provide the answers Epstein needs when it comes to the futures of Anthony Rizzo, Kris Bryant, Javier Baez, Willson Contreras, Kyle Schwarber and company.
  • The Giants have extended a non-roster spring training invitation to catcher Ricardo Genoves, per Kerry Crowley of the Bay Area News Group. Given the timing, it’s safe to assume Genoves inclusion in the spring cohort comes as a result of the injury that will keep Aramis Garcia out for most of next season. That said, his inclusion is more about gaining a learning experience, and he’s not actually in the running for the Giants’ backup catching spot, per The Athletic’s Andrew Baggarly. Still, it seems a good opportunity for the 20-year-old Venezuelan backstop, and perhaps one that will put him on the radar of league officials league-wide. He was signed by the Giants at the open of the international signing period in 2015, but he tapped into real power at the dish for the first time this past season. Genoves managed a .265/.335/.469 line with 9 home runs in 51 games with Salem-Keizer of the Northwest League and Augusta in Low-A. 

Cubs’ Players, Personnel on the State of the Team

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The Cubs are one of two teams without a guaranteed signing this offseason, and there’s a good chance their caution continues. By all accounts, the Cubs will have a chance at returning to National League prominence in 2020 only if they make significant strides internally, per Gordon Wittenmyer of the Chicago Sun Times. On that front, there are definitely issues to address.

Star shortstop Javier Baez made the point clearly: “The biggest problem to fix? “I think everybody was being there for the team but at the same time for their own numbers.” Wittenmyer also provides a quote from new manager David Ross, who strikes a similar tone in saying, “I think we’ve got to let everybody talk about us like it use to be – not us talking about other people.”

Given the success of the Nationals’ last season, driven by a persistent narrative of clubhouse camaraderie, coupled with the clear morale questions at the heart of the Astros’ controversy heading into the season, soft skills are having a moment in MLB right now. The Cubs will give the 2020 season another test case. That is, if they can make the clubhouse adjustments the team has been talking about for two seasons now.

As has been the case for most of the offseason, however, the conversation never veers far from the grievance filed by Kris Bryant, per The Athletic’s Sahadev Sharma. The Cubs continue to wait for a resolution.

President of Baseball Operations Theo Epstein answered questions about the open case – as he has all offseason – at the outset of the Cubs’ Convention. Said Epstein, “Our role was to show up when they told us to show up, answer questions truthfully, which we did, and sit back and wait for a decision. There were a lot of documents and a lot of arguments involved in the case. We respect the role of the arbitrator. He’s gotta work through everything methodically until he’s confident in his decision. Then, he can move forward. It’s out of our control; we’re not going to worry about it. Whenever it happens, it happens.”

A ruling would theoretically free the Cubs to take final offers on a Bryant trade and consummate a deal, if there’s one out there to Epstein’s liking. Moving Bryant would get the Cubs under the luxury tax, clearly a benchmark they’d like to clear prior to the 2020 season.

That said, don’t expect the financial floodgates to open. Removing Bryant’s contract ducks the tax, but not enough to create space to sign, say, Nicholas Castellanos. Other than Castellanos, who took a definite liking to Wrigley Field last season, there aren’t a lot of free agents that make sense for the Cubs at this time. Not anymore. There’s certainly nobody available that comes close to matching Bryant in talent. There are other ways the Cubs could sneak under the tax that would be less harmless to their on-field product in 2020, so moving Bryant only makes sense if the return satisfies Epstein’s asking price.

For now, the waiting game continues on the Northside, much to the chagrin of the fanbase. Their inactivity is well-documented, addressed yesterday by MLBTR’s Anthony Franco here, but it remains one of the stories of the offseason. The only imaginable impact move left for the Cubs is dealing Bryant for a young collection of  players that can help both now and in the future. Whether a team like the Braves or Diamondbacks pony up talent enough for Epstein to pull the trigger is the unknown variable that won’t come to light until after the resolution of the Bryant case.

Until then, as Epstein put it (per Sharma), “I think we’re realistic about it. It’s been a few years with some of these guys that we’ve tried to get something done. It hasn’t happened, but that doesn’t mean it can’t in the future. It’s really hard to predict the future. Sometimes you’re only one phone call away from signing a guy to a long-term contract. Sometimes you’re one phone call away from a deal. What’s most likely is the status quo.”

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