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The Cubs will consider major trades as they look to improve a team with holes in center field, the rotation, and the bullpen.

Guaranteed Contracts

• Yu Darvish, SP: $81MM through 2023
• Jason Heyward, RF: $86MM through 2023
• Jon Lester, SP: $25MM through 2020.  Includes mutual option for 2021.
• Craig Kimbrel, RP: $33MM through 2021.  Includes club/vesting option for 2022.
• Anthony Rizzo, 1B: $16.5MM through 2020.  Includes club option for 2021.
• Tyler Chatwood, P: $13MM through 2020.
• Kyle Hendricks, SP: $55.5MM through 2023.  Includes club option for 2024.
• Jose Quintana, SP: $10.5MM through 2020.
• Daniel Descalso, 2B: $3.5MM through 2020.  Includes club option for 2021.
• David Bote, 3B/2B: $15MM through 2024.  Includes club options for 2025 and ’26.

Arbitration-Eligible Players (projections via MLBTR contributor Matt Swartz)

• Kris Bryant, 3B/OF – $18.5MM
• Javier Baez, SS – $9.3MM
• Kyle Schwarber, LF – $8.0MM
• Willson Contreras, C – $4.5MM
• Albert Almora, CF – $1.8MM
• Kyle Ryan, RP – $1.1MM
• Jharel Cotton, SP – agreed to $640K salary
• Non-tendered: Addison Russell, Danny Hultzen

Free Agents

• Nicholas Castellanos, Cole Hamels, Addison Russell, Ben Zobrist, Steve Cishek, Brandon Kintzler, Pedro Strop, David Phelps, Derek Holland, Brandon Morrow, Tony Barnette, Kendall Graveman

This year the Cubs failed to reach the playoffs for the first time since their rebuild ended in 2015.  Following a disappointing 84-win season, Joe Maddon’s five-year term as manager came to an end.  Despite Maddon achieving the impossible with the Cubs’ 2016 championship, the club showed little interest in a new deal.  It was a pretty typical progression – the Cubs’ performance had become increasingly disappointing, particularly with 2018’s one-game Wild Card ouster and missing the playoffs entirely in ’19.  That’s not a situation where a manager is typically re-signed, even if most of the blame falls on the players and front office.  Maddon is famously laid-back, so the team brought David Ross in to light a fire under the players as well to restore camaraderie.  Ross seems like he’ll be able to improve those situations, and should be equally adept as Maddon in dealing with the media.  Where Ross’ lineup and in-game tactics rank remains to be seen, as he has no prior managerial experience.  The Cubs protected against that concern by hiring former Padres manager Andy Green to serve as Ross’ bench coach.

After hiring Ross, Cubs president Theo Epstein kicked off his offseason by making easy calls on club options, retaining Anthony Rizzo and Jose Quintana and moving on from pitchers David Phelps, Brandon Morrow, Kendall Graveman, and Tony Barnette.  The team also picked up Jharel Cotton, an affordable righty who can compete for a fifth starter or long relief role.  Cotton, 28 in January, looked promising back in 2016 before injuries set in.  The Cubs also made the overdue decision to part ways with infielder Addison Russell, oddly accentuating that they did so because his salary was getting too high.  That the Epstein regime did not cut ties with Russell due to the domestic violence allegations against him more than two years ago is something that many of the team’s fans will continue to find disturbing.

Looking forward, let’s start with the matter of the Cubs’ payroll.  Epstein’s not talking about it, but the Cubs were one of only three teams to exceed the $206MM luxury tax line in 2019.  Back in September, the Associated Press projected the Cubs’ penalty for this infraction to be $6.34MM.  On the surface, it’s difficult to call the team cheap when they’re running a top-three payroll in baseball.  On the other hand, it’s hard to see why a 20% tax on the overage would serve as a real impediment to any major market team.  It’s worth questioning what would constitute a reasonable player payroll for these corporations, rather than taking their word for it or accepting the luxury tax threshold as a salary cap.

Back of the napkin, the Cubs have contract commitments of about $135MM for 2020, plus an arbitration class that should run around $44MM.  There seems to be enough wiggle room for one premium player or at least several decent ones, right?  But the reality is that the team’s competitive balance tax payroll is higher, estimated around $210MM for 2020 already.  As the AP explains, “Luxury tax payrolls are based on the average annual values of contracts for players on 40-man rosters and include $14.5 million per team in benefits.”  Every dollar the Cubs spend between $208MM-228MM comes with a 30% tax, and every dollar they spend between $228MM-248MM comes with a 42% tax.  If the Cubs were to sign Gerrit Cole at a $35MM AAV, it would be more like paying him $48MM in 2020 due to the taxes they’d incur, and it would leave little room for other notable additions without accompanying subtractions.

On the other hand, with Lester, Quintana, and Chatwood off the books in ’21, the Cubs could get under the $210MM base tax threshold in that season, at which point all the taxes would go away.  Would it be crazy to go to $247MM in 2020, pay a $14MM tax once, and then reset?  I don’t think so, but $248MM represents a harder line in the sand since spending beyond that point would be taxed at 75%, and the Cubs’ top draft pick would move down ten spots.  After going down the rabbit hole here, you start to see that there’s almost no chance the Cubs will add more than $38MM in CBT payroll this winter, and they could easily choose to draw the line at $18MM added.

It certainly seems like the Cubs will be sitting out on the major free agents for the second consecutive winter.  Obviously, any of the big dogs would greatly increase the team’s chances of returning to the playoffs in 2020.  With Cole Hamels having signed with the Braves, the Cubs’ rotation sets up as Yu Darvish, Kyle Hendricks, Jose Quintana, and Jon Lester.  With Quintana, Lester, and Chatwood due for free agency after the season, another long-term investment in the rotation in the form of Cole or Stephen Strasburg would be worth considering.  Third baseman Anthony Rendon is a tougher fit, as signing the game-changing star would necessitate playing Kris Bryant full-time at an outfield corner, and Bryant has never spent even 500 innings in the outfield in an MLB season.  Or, Bryant could be traded this winter.

Bryant is only under team control for two more seasons, with a slight chance of 2020 becoming his walk year if he wins his service time grievance.  Though Bryant winning the grievance is considered unlikely, I don’t see why, since the Cubs’ manipulation of his service time to gain a seventh year of control was the most blatant case in recent history.  It doesn’t seem crazy to think that an independent arbitrator could rule in his favor.  Regardless, if the Cubs are to seriously entertain trading Bryant this winter, it would have to be after the decision is revealed.  Moving Bryant generally seems like robbing Peter to pay Paul, as Bryant is a five-win player who should earn around $20MM this winter, and that’s a great deal for the Cubs.  Still, it’s possible to trade a five-win player and emerge better for it.

Who might pursue Bryant this winter?  We could start with Rendon’s suitors.  Bryant is about 19 months younger than Rendon, but Rendon has become better on both sides of the ball and projects to remain a little better in the short-term.  The Dodgers, Rangers, and Nationals, as Rendon suitors, could view Bryant as an interesting Plan B, but those same clubs could also look at Josh Donaldson.  If we’re assuming Bryant will mostly be deployed at the hot corner, the Angels, Braves, Phillies, Indians, Marlins, Mets, Rays, or Twins could be options.  Bryant could be especially interesting for teams that would never be able to sign a player of his caliber in free agency.  I can only speculate so much, but I imagine young, controllable starting pitching would be a key part of a Bryant deal for the Cubs.  If the Cubs actually do move Bryant and don’t want to replace him with the large salary of Rendon or Donaldson, they could plug in David Bote as his replacement at third base.

Similarly, we’ve seen the suggestion the Cubs could trade catcher Willson Contreras this winter.  Contreras, 27, is one of the best-hitting catchers in the game, and he has three years of remaining control.  He’s poorly regarded as a pitch framer, so the teams that lost out on Yasmani Grandal won’t necessarily be all over Contreras.  The Angels, Astros, Blue Jays, Mets, and Rangers could potentially seek a boost behind the plate and consider Contreras.  But the Cubs, much like with any potential Bryant trade, would increase their own exposure by elevating Victor Caratini to regular status, especially with Grandal off the board.  “The Cubs are going to make a move,” wrote ESPN’s Jeff Passan, so it seems that after years of threatening a possible position player shakeup, the club will actually do so to some degree this winter.

While the Cubs’ infield could easily be left alone, with Nico Hoerner stepping in as the regular second baseman, the team’s outfield situation seems more unsettled.  Heyward has a spot locked down, and has at least settled in as a two-win player who could be used in center field in the short-term.  I don’t think the Cubs want to commit to keeping Heyward out of his natural right field position, however, which is one reason a reunion with Nicholas Castellanos seems unlikely.  Mike Moustakas, a pretty good but flawed position player without a qualifying offer attached, snagged a four-year, $64MM deal from the Reds.  Castellanos, almost three and a half years younger than Moose, seems to have a chance at topping that contract.  Given Castellanos’ defensive limitations and their current payroll crunch, that doesn’t seem like a contract the Cubs will find palatable.

Plus, Kyle Schwarber already serves the role as a solid bat-first corner outfielder for the Cubs, and he should clock in at half Castellanos’ salary without a long-term commitment.  While Schwarber is certainly a trade candidate, the simplest scenario for the Cubs may be to leave him in left and Heyward in right, importing a quality starting center fielder.  That would bump Albert Almora to a fourth outfielder role or trade bait, not that much return would be expected.  The Cubs have Shogo Akiyama on their radar as a possible center field solution, according to Patrick Mooney of The Athletic.  Jackie Bradley Jr. could be a trade option, though not a game-changer, and his $11MM salary projection is problematic.  Starling Marte would be an excellent target if the Pirates are willing to move him in the division, and his $11.5MM CBT hit would be worth it.  Aside from Akiyama, the free agent market is sparse at center field, with only Kevin Pillar and Brett Gardner qualifying as potential regulars.  Though the Cubs’ center fielder doesn’t necessarily have to be their leadoff hitter, it would be nice to kill two birds with one stone.  Akiyama has run an OBP of .385 or better for the Seibu Lions in each of the last five seasons, so the Cubs’ interest makes sense.

We haven’t talked yet about Ian Happ, the Cubs’ first-round pick from 2015.  The 25-year-old has a career 112 wRC+ in 1,031 plate appearances, though the switch-hitter’s success has been largely against right-handed pitching.  He’s been a man without a position in his big league career, though perhaps 2020 could represent a chance to earn semi-regular playing time in center field if the Cubs don’t make a significant pickup.  Happ is also a trade option, though the Cubs could be selling low.

Moving Heyward to center field in the short-term is also palatable.  That could allow the Cubs to consider free agents like Avisail Garcia, Yasiel Puig, Kole Calhoun, and Steven Souza.  None represent a clear upgrade for the Cubs, however.  Mookie Betts remains the crown jewel of the trade market, and of course would be a huge one-year addition for the Cubs.  As the GM who drafted Betts, you’d have to think Epstein will at least inquire, but a salary projection near $30MM could be an issue for the Cubs the same way it is for the Red Sox.  More down-to-earth trade options could include Trey Mancini or Whit Merrifield (who could also help at second base).

The Cubs would be well-served to think bigger with their open rotation spot than Jharel Cotton, Adbert Alzolay, and Chatwood, but it’s unclear how big they’ll go.  I think they’d top out at a $10MM a year type of free agent, and possibly wouldn’t go that far.  The decision not to issue a qualifying offer to Hamels showed, if nothing else, they weren’t comfortable risking him accepting a one-year, $17.8MM deal, even though that’s the contract he ended up getting from the Braves.  It’s also quite possible the Cubs’ rotation will be addressed with an affordable young arm if they wind up trading a position player.

The Cubs’ bullpen is of greater urgency.  Given their commitment to Kimbrel, they’ve got to try to fix him after a disastrous stint in which he posted a 6.53 ERA with nine home runs allowed in 20 2/3 innings.  After Kimbrel, Rowan Wick and Kyle Ryan probably have spots locked down.  Veterans Pedro Strop, Steve Cishek, and Brandon Kintzler are all free agents, though Strop has expressed a desire to return.  Ideally, the Cubs would add a stable veteran who could step into the ninth inning if Kimbrel falters.  Reliability is not easily found among free agent relievers, though Will Harris might fit the bill.

Assuming Bryant’s grievance goes the Cubs’ way, their core position player trio of Bryant, Javier Baez, and Anthony Rizzo remains under control through 2021.  The three players should be good for 12 WAR at a cost of about $44MM in total in 2020.  While that’s obviously not the strong competitive advantage of paying all three players less than $9MM total for 13+ WAR, as they did in each of the 2016 and ’17 seasons, it’s still a great price for the talent and not something to be squandered.  Logically, if there’s a time for the franchise to take a step back and reset, it’s after the 2021 season.  With the team’s payroll issues still in full force, creativity will be required by Epstein and company this winter.