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Red Sox Promote Paul Toboni To Assistant GM

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The Red Sox are promoting Paul Toboni to assistant general manager, as first reported by Chris Cotillo of MassLive. The 33-year-old had held the title of vice president of amateur scouting and player development.

Toboni was among the internal options whom the Sox considered in their search for a new front office leader after dismissing Chaim Bloom. He’d have had to jump a number of people on the organizational hierarchy to land that position, which always made him a long shot for the top job. Nevertheless, he lands a promotion a few months later under new chief baseball officer Craig Breslow.

Boston now has four assistant GMs: Toboni, Raquel Ferreira, Eddie Romero and Mike Groopman. Toboni moved quickly into the upper ranks of the organization. A collegiate infielder at Cal, he was hired by the Sox as a scout in 2015. By 2020, he’d been tabbed to orchestrate the club’s amateur drafts — a role he held through 2022.

While the Sox have a number of assistant general managers, they don’t have anyone currently holding the GM title. Breslow suggested at the time of his hiring as chief baseball officer that he wasn’t in a rush to tab a GM, who would serve as his top assistant in the front office.

Latest On Shota Imanaga

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Jan. 9: Jon Heyman of the New York Post reports this morning that both the Giants and Angels now “appear to be looking elsewhere” (Twitter links). Heyman suggests that both the Red Sox and Cubs are “very much” still alive in the Imanaga bidding. That runs counter to reports from the weekend and from yesterday, though bidding on any free agent is, of course, quite fluid. Imanaga has a bit more than 48 hours remaining to come to terms with a team.

Jan. 8, 3:55pm: Chris Cotillo of MassLive reports that the Sox are considered a “long shot” to get Imanaga as things currently stand.

3:45pm: Star NPB left-hander Shota Imanaga will see his 45-day posting window come to a close on Thursday, meaning it’s only a matter of days before the 30-year-old will decide on his first big league team. Bidding for Imanaga has reportedly been strong, as he’s drawn interest from a wide range of teams thus far in his first foray into MLB’s open market. As the bidding period winds down, Imanaga’s market has unsurprisingly begun to take firmer shape.

Sankei Sports in Japan reports that the Angels and Giants are currently the leading candidates to sign Imanaga, although no decision has been made just yet. Similarly, MLB.com’s Mark Feinsand suggests that the Giants are emerging as the favorites to sign the southpaw, though Feinsand adds that each of the Angels, Cubs and Red Sox remain in the fold to some extent. While there’s still a number of ways which the left-hander’s final decision could go, it’s at least notable that Feinsand characterizes a final four of sorts, while the reports out of Japan have the field narrowed further yet.

The Giants and Angels are both strong fits for Imanaga, who’s expected to top countryman Kodai Senga’s five-year, $75MM contract with the Mets. San Francisco acquired former AL Cy Young winner Robbie Ray on Friday in a surprising trade with the Mariners, but Ray isn’t expected to pitch until midseason as he recovers from Tommy John surgery. Similarly, right-hander Alex Cobb will open the year on the injured list while recovering from October hip surgery.

That leaves the Giants with ace Logan Webb as the most (arguably only) solidified member of the rotation. Veteran Ross Stripling, top prospect Kyle Harrison and 2023 rookies Keaton Winn and Tristan Beck are among the candidates to round out the staff, but there’s a good deal of uncertainty beyond that group. It’s true that Imanaga himself comes with his own uncertainty — he’s untested against big league hitters — but MLB scouts are intrigued enough by him that some believe his contract could approach nine figures. Clearly, there’s a prevailing belief throughout MLB that Imanaga is a legitimate mid-rotation arm, at the least.

A few hundred miles to the south, the Angels are facing some rotation questions of their own. Reid Detmers, Griffin Canning and Patrick Sandoval are all locked into spots, although Detmers and Sandoval both had down 2023 showings relative to their 2022 performance. That’s even more true of veteran Tyler Anderson, who had an All-Star ’22 showing with the Dodgers before posting a 5.43 ERA in year one of a three-year, $39MM free agent deal with the Halos. The Angels recently took a low-cost flier on Zach Plesac and have reportedly been prioritizing Blake Snell in the wake of Shohei Ohtani’s departure, but Imanaga presents a mid-rotation option for them as well.

The Red Sox, meanwhile, will roll out a new-look rotation with or without Imanaga. Gone is oft-injured ace Chris Sale, who was shipped to the Braves (with cash) in exchange for second baseman Vaughn Grissom. He was quickly replaced by newly signed Lucas Giolito, who’s currently in line to be joined by some combination of Brayan Bello, Tanner Houck, Nick Pivetta, Garrett Whitlock and Kutter Crawford.

As for the Cubs, they’ve been MLB’s least-active team this winter — at least when it comes to actually pushing deals across the finish line. Chicago has been connected to a litany of free agents and a handful of trade targets, but thus far the Cubs haven’t added a single player to their roster aside from catcher Brian Serven, whom they claimed off waivers from the Rockies last week. Chicago’s rotation currently includes Justin Steele, Kyle Hendricks and Jameson Taillon, with veteran Drew Smyly and young arms like Hayden Wesneski, Jordan Wicks, Ben Brown and Javier Assad all in the mix for starts as well. It’s a relatively solid group, but the Cubs figure to make some kind of move to replace the outgoing Marcus Stroman.

Dating back to 2019, Imanaga boasts a 26.2% strikeout rate and 5.9% walk rate in addition to a cumulative 2.79 earned run average — including a no-hitter in the 2022 season. He’s not overpowering in terms of velocity, though MLBTR contributor Dai Takegami Podziewski noted back in September that he’d added some life to his heater and was averaging between 92-93 mph during the 2023 campaign. In addition to the guaranteed money owed to the pitcher himself, Imanaga’s new team will need to pay a release fee to his former team, the Yokohama DeNA BayStars, which would be equal to 20% of the contract’s first $25MM, plus 17.5% of the next $25MM and 15% of any dollars thereafter.

Red Sox Fielding Trade Interest In Masataka Yoshida, Kenley Jansen

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The Red Sox have received trade interest in left fielder Masataka Yoshida, report Jen McCaffrey and Ken Rosenthal of the Athletic. McCaffrey and Rosenthal write that while the Sox aren’t actively shopping Yoshida, they’re open to ways to restructure the outfield.

That aligns with a report from Alex Speier of the Boston Globe last week the Sox were considering dealing an outfielder. The Sox would have more suitors if they shopped an affordable, controllable player like Jarren Duran, Ceddanne Rafaela or Wilyer Abreu. Finding a suitable match on Yoshida would be more difficult, but it’s a possibility that’d clear some desired spending room.

Another move that’d allow the Sox to shed some money: a trade of closer Kenley Jansen. Speier reported this evening that Boston is entertaining interest in the four-time All-Star. Yoshida and Jansen were each free agent pickups last offseason.

Boston signed Yoshida to a five-year, $90MM contract. (They also paid a $15.375MM posting fee to Yoshida’s former team, the Orix Buffaloes.) It was a bet on the left-handed hitter transitioning smoothly to MLB pitching. The 30-year-old had mixed results in his first big league campaign. Yoshida hit .289/.338/.445 over 580 plate appearances. He showed strong strike zone awareness and excellent pure contact skills, yet it wasn’t an overwhelming offensive performance.

Yoshida hit 15 home runs and walked less than 6% of the time he stepped to the plate. Listed at 5’8″ and 176 pounds, he doesn’t have the raw power of a prototypical slugger. Yet the profile is built around his bat, as Yoshida has drawn below-average reviews for his glove dating back to his time in Japan. He’s limited to left field or designated hitter and received subpar grades from Defensive Runs Saved and Outs Above Average.

Detractors pointed to those defensive and power questions when Yoshida was available via the posting system last winter. The Sox, under former chief baseball officer Chaim Bloom, were confident he’d hit enough to overcome that. With Bloom having since been replaced by Craig Breslow, the front office might be less bullish on his projection.

Yoshida’s contract calls for $18MM salaries for the next four seasons. It’s unlikely he’d have landed a $72MM deal covering his age 30-33 campaigns if he were a free agent this winter. As a result, Boston would probably have to offset a chunk of the money to move him — either by including cash considerations or taking some money back in the deal.

Jansen would be a much different trade candidate. His $16MM salary next season isn’t far below what Yoshida will make. He’d be a much shorter-term commitment, though, as he’ll be a free agent after 2024. Jansen had a solid but not overpowering first season with the Sox, pitching to a 3.63 ERA over 44 2/3 innings. He struck out 27.7% of opponents, an above-average mark that nevertheless represented the lowest rate of his career. He still successfully nailed down 29 of 33 save chances, but he wasn’t quite as dominant as he’d been for the Dodgers or Braves.

Boston has a fair amount of depth in both the outfield and the bullpen. That at least opens the possibility of offloading cash in those areas to clear space for other targets. Speier wrote tonight the front office is still seeking starting pitching and a right-handed power bat.

The Sox have been tied to free agent Teoscar Hernández throughout the offseason. Meanwhile, Mark Feinsand of MLB.com reports that Boston is also among the team showing interest in Jorge Soler. Either player would provide plenty of juice from the right side. A Yoshida trade would open a path to playing time in left field or DH. However, Speier indicates the Red Sox have been unwilling to offer more than two guaranteed years to Hernández, who is holding out for a three-plus year pact. It’s unclear if they’d be open to a third year on Soler.

In any case, there are obviously a number of possibilities the front office is still considering. The Sox have also been tied to a number of free agent rotation options, including Blake Snell, Jordan Montgomery and Shota Imanaga. Recent reporting has indicated that Imanaga appears a more realistic target than Snell or Montgomery, although the NPB left-hander could top $100MM himself. Speier characterizes the Red Sox as “lurking” on Imanaga but indicates they may not be among the most involved suitors. The southpaw will make his decision before the posting window closes next Thursday.

Angels, Padres, Pirates Interested In Michael A. Taylor

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Free agent center fielder Michael A. Taylor is drawing interest from the Angels, Padres and Pirates, reports Robert Murray of FanSided. Murray adds that the Halos are also considering Adam Duvall as a free agent outfield target.

Taylor should have the broader market of the two veterans. His ability to play an excellent center field makes him a strong fit on a number of teams. He could operate as a glove-first regular for clubs without a strong in-house option in center or serve as a high-end fourth outfield target for others. The Dodgers, Reds, Blue Jays, Red Sox and Mets have also been linked to Taylor earlier in the offseason. Toronto and New York subsequently signed Kevin Kiermaier and Harrison Bader, respectively, likely taking them out of the mix.

Boston acquired Tyler O’Neill as a right-handed hitter with the ability to play anywhere in the outfield. That could reduce their urgency on Taylor, but Murray suggests they’re still involved. He adds that a return to the Twins, with whom Taylor spent the 2023 campaign, also remains a possibility.

For teams that aren’t going to entertain a run at Cody Bellinger, Taylor is the top center fielder on the open market. He remains a high-end defender even as he enters his age-33 season. Taylor has been a below-average hitter for the bulk of his career, but he’s coming off one of his better offensive showings. He popped a career-best 21 home runs in just 388 plate appearances. Taylor still struck out in more than a third of his plate appearances and hit .220 with a meager .278 on-base percentage. Yet the defense and the ability to run into 15-20 homers while hitting in the bottom third of a lineup makes him a serviceable regular.

The Angels have a projected outfield of Taylor Ward, Mike Trout and Mickey Moniak. Ward missed the final couple months of last year after sustaining facial fractures on a frightening hit-by-pitch. Trout hasn’t reached 120 games or 500 plate appearances in a season since 2019 because of various injuries. Moniak posted solid bottom line results last year, hitting .280/.307/.495 through 323 plate appearances. However, that came with a 35% strikeout rate and a 2% walk percentage that are even worse than Taylor’s career baselines.

Moniak is a clear regression candidate who is better suited in a fourth outfield capacity. Even if the Halos are optimistic about his ability to produce against right-handed pitching, the former #1 overall pick has a .172/.200/.230 slash in 91 career plate appearances versus lefties. The righty-hitting Taylor has been better against southpaws than against right-handed pitching, as one would expect. Since the start of 2020, he’s a .257/.317/.455 hitter with the platoon advantage.

Duvall also hits from the right side. While he has had reverse platoon splits in recent years, he’s a better overall offensive player than either Moniak or Taylor — albeit with a similar low-OBP, power profile. He hit 21 homers in 353 plate appearances for the Red Sox last season, running a .247/.303/.531 slash. Duvall can play some center field but is better suited for a corner spot entering his age-35 season.

As for the other clubs recently linked to Taylor, each of Pittsburgh, San Diego and Minnesota are viable fits. The Padres need to bring in multiple outfielders after trading Juan Soto and Trent Grisham. They’d seemingly prefer to keep Fernando Tatis Jr. in right field rather than moving him up the middle. José Azocar (a career .249/.292/.341 hitter) and prospect Jakob Marsee are the top internal options in a center field position that requires an outside pickup.

Minnesota leaned heavily on Taylor last year as knee injuries kept Byron Buxton to designated hitter. While the Twins have expressed hope that Buxton could handle outfield work again in 2024, they can’t count on him to make 120+ starts at the position.

The Pirates could turn center field back to Jack Suwinski, although public metrics were mixed on his defensive performance. Bryan Reynolds can handle center on occasions but fits best in left. Right field is a question mark, with trade pickup Edward Olivares likely battling Joshua Palacios for work. Andrew McCutchen will see the majority of his time at designated hitter while rotating through the corners. Signing Taylor could allow the Bucs to kick Suwinski to right field and boast a strong defensive outfield.

Kiermaier and Bader each signed one-year pacts worth $10.5MM. Taylor could be in line for something similar, although it wouldn’t be a surprise if he landed a two-year deal at a lower annual value but a slightly better overall guarantee.

Yankees Interested In Dylan Cease

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The Yankees were connected yesterday to free agent Blake Snell but it appears they are exploring the trade market as well. Ken Rosenthal of The Athletic reports that the Yankees, and the Orioles, have “sincere” interest in Dylan Cease. The O’s were previously connected to Cease and Roch Kubatko of MASNsports.com reported earlier this week that they “remain engaged” with the White Sox. Rosenthal adds that the Dodgers, Cardinals and Red Sox, all previously reported to have interest in Cease, are possibly still in the mix, with other clubs perhaps involved as well. The Braves and the Reds, who once had interest in Cease, appear to have moved on to other targets with Atlanta trading for Chris Sale and the Reds signing Frankie Montas and Nick Martínez.

Rumors have been flying around Cease all winter but he remains on the White Sox for now. About a month ago, it was reported that the White Sox were “pulling back” on the Cease talks. That wasn’t to take him off the market, but rather that the Sox wanted to wait until Yoshinobu Yamamoto signed to find out if clubs that missed on him would pivot to Cease as a fallback.

With the interest from the Yankees, that would appear to be exactly the case. They were one of the clubs that was heavily connected to Yamamoto before he signed with the Dodgers, leaving the Yanks looking elsewhere. They have considered Snell as well as free agent Jordan Montgomery but are checking in on Cease as well.

For the Yanks, they have Gerrit Cole cemented into the top spot of their rotation but things get less clear after that. Carlos Rodón and Nestor Cortes have the potential to be excellent contributors but both of them struggled badly in 2023, both with injuries and poor performance. Clarke Schmidt will likely be in the mix towards the back of the rotation, but the club subtracted from its depth in the Juan Soto trade, as Michael King, Drew Thorpe, Jhony Brito and Randy Vásquez are all Padres now. Adding another starting pitcher, and having Rodón and Cortes bounce back a bit, would give the club a very strong front four, with Schmidt likely in the five spot and pitchers like Clayton Beeter, Yoendrys Gómez, Luis Gil and Will Warren providing the depth.

Cease would upgrade any rotation in the league, despite a relative down year in 2023. He had a 2.20 earned run average in 2022 but that figure jumped to 4.58 last year, though his underlying numbers paint a less drastic picture. His 2022 success wasn’t likely to be sustainable anyway, given his .260 batting average on balls in play and 82.3% strand rate, both of which are on the lucky side. Those numbers moved to .330 and 69.4% in 2023, pushing some extra runs across. His strikeout and swinging strike rates did tick down slightly but were both still well above average. His 3.10 FIP in 2022 jumped to 3.72 in 2023, suggesting a far less concerning shift, while his SIERA went from 3.48 to 4.10.

Looking at the past three years as a whole evens out some of that luck and paints and an incredibly flattering portrait. He’s made 97 starts since the start of 2021 with a 3.54 ERA and 29.8% strikeout rate. The 10.1% walk rate is on the high side but his 12.6 wins above replacement from FanGraphs in that time puts him eighth among all MLB pitchers.

His appeal goes beyond his skills, as his earning power is still capped by the arbitration system. MLBTR contributor Matt Swartz projects Cease for a salary of $8.8MM this year and he will be due a raise in 2025 before reaching free agency.

The Yankees currently have a competitive balance tax figure of $290MM, according to Roster Resource. They are set to pay the tax for a third straight year in 2024, which sets them up for escalating penalties. They are already above the third tier of $277MM and nearing the fourth and final tier of $297MM. That means they are facing a tax rate of 95% on current spending until they go over the last line and then have a 110% rate on spending from there.

Signing a player like Snell or Montgomery would likely require the Yanks to give out a salary of around $25MM or more, with the taxes effectively doubling that. Given that Cease will be making around a third of that salary figure, that would obviously make him more attractive.

But the flip side of that equation is that Cease will also require sending something to the White Sox in return, likely a very significant package of talented young players. The Yanks just sent away a big batch of young pitchers in the Soto deal and may be reluctant to make another sizable dent in their talent pipeline. As for what the Sox would be looking for, Rosenthal says they are “staying open-minded” and “not necessarily inclined to favor a team that could include major-league-ready pitching.”

With the O’s also having “sincere” interest, they might have an edge on the Yankees in terms of having the talent to get a deal done. Despite constantly graduating prospects to the major league level in recent years, they are still considered to have the top farm system in the league by many evaluators. Jackson Holliday is almost certainly untouchable but the club also has guys like Colton Cowser, Coby Mayo, Jordan Westburg, Samuel Basallo, Heston Kjerstad and Joey Ortiz without enough open positions for all of them.

The club has also shown a bias against bold moves, both in the trade market and free agency, which is why they have that loaded farm system and almost no money on the books. If they decide now is the time to strike, Cease would fit nicely into a rotation with lots of talent but limited experience. Kyle Bradish and Grayson Rodriguez are at the top of the rotation for now, after each showed encouraging signs in 2023, but Bradish has less than two full years in the big leagues and Rodriguez less than one. Then there’s John Means, who has hardly pitched in the last two years due to Tommy John surgery, and guys like Dean Kremer and Cole Irvin options for the back end.

As mentioned, clubs like the Dodgers, Cardinals and Red Sox may still be involved and that might not even be the extent of the market. But with Yamamoto off the board, it seems the pitching market is broadly heating up and a Cease trade could happen at any time now.

MLBTR Podcast: Yamamoto Fallout, the Sale/Grissom Trade and Transaction Roundup

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The latest episode of the MLB Trade Rumors Podcast is now live on Spotify, Apple Podcasts, and wherever you get your podcasts! Make sure you subscribe as well! You can also use the player at this link to listen, if you don’t use Spotify or Apple for podcasts.

This week, host Darragh McDonald is joined by Anthony Franco of MLB Trade Rumors to discuss…

Check out our past episodes!

The podcast intro and outro song “So Long” is provided courtesy of the band Showoff.  Check out their Facebook page here!

Red Sox Designate Mauricio Llovera For Assignment

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The Red Sox officially announced their deal with right-hander Lucas Giolito, with fellow righty Mauricio Llovera designated for assignment in a corresponding move.

Llovera, 28 in April, was just acquired from the Giants in a cash deal in July. He went on to toss 29 2/3 innings over 25 appearances after coming to Boston, with a 5.46 earned run average in that time. He had spent time with the Phillies and Giants and now has 59 innings of MLB experience with a 5.80 ERA.

He has fared much better in the minors, with a 2.82 ERA at the Triple-A level in 92 2/3 innings over the past three years. He has struck out 25.9% of Triple-A hitters faced while giving out walks to 8.8% of them. It’s also perhaps worth pointing out that a decent chunk of that came in the hitter-friendly Pacific Coast League while he was in the Giants’ system.

The Sox will now have a week to trade him or pass him through waivers, though he would be eligible to elect free agency in the latter scenario since he has a previous career outright. His strong Triple-A results could lead to another club putting in a claim but Llovera is out of options, which will limit his appeal as a depth arm.

Red Sox Sign Lucas Giolito

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The Red Sox are taking on a flier on Lucas Giolito, announcing to today that they have signed the right-hander. It is reportedly a two-year, $38.5MM guarantee that allows the CAA client to opt out after the first season. Giolito will collect an $18MM salary next year and would receive a $1MM buyout if he exercises the opt-out. His ’25 salary is worth $19MM.

If he doesn’t opt out next winter, a conditional option kicks in covering the 2026 campaign. Were Giolito to throw fewer than 140 innings in 2025, the Sox would have a $14MM club option. If he reaches or tops 140 frames, he’d convert that provision to a $19MM mutual option. Regardless of the option value, there’d be a $1.5MM buyout. The deal also contains $1MM in performance bonuses in each of the next two seasons.

It’s a modified pillow contract for the 29-year-old. That reflects a dismal final few months of last season. Giolito looked on track for a nine-figure deal early in the summer. Over his first 21 starts with the White Sox, he carried a 3.79 ERA while striking out more than a quarter of batters faced. Chicago’s fall out of contention made him one of the top starters available at the deadline.

A trade sending Giolito alongside reliever Reynaldo López to the Angels looked like a boost to his market value. Joining a fringe contender gave him an outside shot at a playoff berth. More meaningfully for his free agency, it took the qualifying offer off the table, as players who change teams midseason can’t be issued the QO.

That’s not how things played out. Giolito was one of the worst pitchers in MLB from the deadline onwards. He made only six starts for the Halos before they placed him on waivers, dumping the remainder of his salary after the team fell from contention to help limbo underneath the luxury tax line. Giolito was hit hard for both Los Angeles and the Guardians, who snagged him off the waiver wire at the end of August.

Over his final 12 appearances, he was tagged for a 6.96 ERA through 63 1/3 innings. He was staggeringly prone to the longball, allowing 21 homers (nearly one in every three innings) over that stretch. His walk rate also spiked. He handed out free passes to nearly 11% of opponents after issuing walks at a manageable 8.3% clip in Chicago.

Short of a major injury, it’d be hard to draw up a more frustrating final two months before free agency. That said, there’s a lot in his career résumé that made him arguably the top reclamation target in the rotation class. Giolito turned in upper mid-rotation results between 2019-21, combining for a 3.47 ERA with an excellent 30.7% strikeout percentage despite the hitter-friendly nature of Chicago’s Guaranteed Rate Field.

He has allowed nearly five earned runs per nine in each of the past two seasons, albeit for different reasons. His 4.90 mark in 2022 was attributable largely to a .340 average on balls in play, by far the highest rate of his career. That dropped to .274 last season, and his early-season results again painted the picture of a solid #3 starter. Then came the late-season homer barrage that left him with a 4.88 ERA at year’s end.

The longball has always been a bit of a problem for Giolito, but his second-half home run rate is unsustainably high. Boston is betting on positive regression in that department, hoping that’ll result in mid-rotation results. While Giolito’s whiffs are down from his 2019-21 peak, he still misses bats at an above-average level. Opposing hitters have swung through 12.2% of his offerings in each of the last two years, which tops the 10.8% league mark for starting pitchers. His fastball sits around 93 MPH and he misses a decent number of bats with both his changeup and slider.

Giolito’s performance has varied over the past few seasons. His durability has not. The 6’6″ hurler has taken the ball almost every fifth day for the last six years. He hasn’t had an injured list stint longer than two weeks at any point in his MLB career. He hasn’t had any arm-related absences as a big leaguer. Giolito has started 29 or more games in each of the past five full schedules and took the full slate of 12 rotation turns during the shortened season. Only Aaron Nola, Gerrit Cole, José Berríos and Patrick Corbin have started more games over that stretch. He’s eighth in the majors in innings pitched since 2018.

A source of volume innings is a sensible addition to a talented but volatile Boston pitching staff. Chris Sale, Nick Pivetta, Brayan Bello, Tanner Houck, Garrett Whitlock and Kutter Crawford are among the in-house options for the Opening Day rotation. Sale has battled various injuries over the past few seasons. Pivetta, Houck, Whitlock and Crawford have all worked out of the bullpen at times. Aside from Crawford, that group has generally found more success in long relief than out of the rotation. Bello’s rotation spot isn’t in jeopardy, but his production dipped at the end of his first full major league season.

That made adding a starter an offseason priority for chief baseball officer Craig Breslow. The Sox were on the periphery of the Yoshinobu Yamamoto market before he signed with the Dodgers. They’d been tied to Jordan Montgomery as well, although recent reporting suggested they were pivoting towards the second tier. Giolito becomes Breslow’s first significant free agent acquisition as Boston’s front office leader. The Sox could still explore the rotation market — they’ve recently been tied to NPB left-hander Shota Imanaga and old friend James Paxton — but this signing may lead them to turn their main focus to another area of need like second base.

The contract falls in line with MLBTR’s prediction of two years and $44MM from the start of the offseason, when we ranked him this winter’s #17 free agent. The two-year guarantee with an opt-out after the first season has become more commonplace in recent years for priority rebound candidates. It affords the player more security than would a straight one-year pact while allowing him to get back to the market after one season if he bounces back.

Giolito turns 30 in July, so he’d be well-positioned for a lofty multi-year pact next winter if he gets on track. Since he was ineligible for the qualifying offer, the signing doesn’t cost Boston any draft compensation. If he pitches well enough to opt out a year from now, the Red Sox would likely make him the QO, allowing them to recoup a draft choice if he only spends one year in Massachusetts.

The Red Sox’s 2024 payroll projection now sits around $187MM, according to Roster Resource. They’re just shy of $200MM from a luxury tax perspective, keeping them $37MM below next year’s lowest threshold. Boston opened last season with a player payroll in the $181MM range after topping $206MM the prior season. They did not exceed the luxury tax threshold in 2023.

Jeff Passan of ESPN first reported the Red Sox were signing Giolito to a two-year, $38.5MM guarantee with an opt-out; Passan was also first with the salary structure and the 2026 option specifics. Chris Cotillo of MassLive first reported the $1MM in annual incentives and specified that the buyout applied regardless of the option scenario.

Image courtesy of USA Today Sports.

Red Sox Claim Max Castillo From Royals

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The Red Sox announced that they have claimed right-hander Max Castillo off waivers from the Royals. The righty was designated for assignment before the holidays but lingered in DFA limbo for a while since the normal seven-day window is paused between Christmas and New Year’s. Boston’s 40-man roster is now at 40, though their deal with Lucas Giolito has not yet been made official.

Castillo, 25 in May, has 59 2/3 innings of major league experience to this point in his career. He has a 5.43 earned run average in that time, having stuck out 18.1% of batters faced, walked 9.3% and kept 44.7% of balls in play on the ground.

Acquired from the Blue Jays alongside Samad Taylor in the Whit Merrifield trade, Castillo spent most of 2023 in Triple-A Omaha. He threw 116 innings at that level with a 4.58 ERA, 19.2% strikeout rate, 5.7% walk rate and 38.8% ground ball rate.

Castillo still has an option year left, so he’ll give the Sox some extra rotation depth for now. The Boston rotation currently projects to feature some combination of Giolito, Brayan Bello, Nick Pivetta, Kutter Crawford, Tanner Houck and Garrett Whitlock but Castillo will give them another arm and can be kept in Worcester. Pivetta is an impending free agent and Giolito can opt out of his deal after 2024 as well. That creates some long-term uncertainty though the Sox have been connected to free agents like Blake Snell and Jordan Montgomery. Perhaps the club will convert Castillo to relief at some point to see if that unlocks another gear. Castillo still has less than a year of service time, giving him the club plenty of cheap control if he takes a step forward.

Red Sox Could Be Looking To Shed Additional Payroll

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The Red Sox made waves on Saturday afternoon, trading seven-time All-Star and 2018 World Series champion Chris Sale to the Atlanta Braves in exchange for young infielder Vaughn Grissom. Boston needed a second baseman, and Grissom can fill that role right away – and potentially for years to come. Still, as talented as Grissom very well may be, it’s hard not to view the trade as something of a salary dump for the Red Sox. Although Sale has spent significant time on the injured list over the past several years, he has flashed great stuff when healthy, and the Red Sox need all the upside they can get if they’re going to compete in the fearsome AL East. By trading the veteran starter to the Braves, along with $17MM in cash, the Red Sox reduced their total payroll commitments by $10.5MM and their luxury tax payroll by approximately $7MM for 2024 (per Roster Resource).

This is not the only trade chief baseball officer Craig Breslow has made to decrease payroll this winter. He flipped Luis Urías to the Mariners just before the non-tender deadline, sacrificing the infielder’s upside to avoid his estimated $4.7MM arbitration salary. He also dealt Alex Verdugo to the Yankees and essentially replaced him with former Cardinals outfielder Tyler O’Neill, saving an estimated $3.7MM in the process. Those sound like relatively inconsequential numbers for a large-market team like Boston, but for what it’s worth, the money the team saved by trading Urías, Verdugo, and Sale adds up to just under $19MM; newly signed starter Lucas Giolito will earn $18MM in 2024.

Indeed, while the Red Sox typically run one of the higher payrolls in the sport, it seems they’ll be operating under a tighter budget this offseason. As reported by Chris Cotillo of MassLive.com, the team has informed at least one free agent that they have to “shed more payroll” before they can pursue him “as aggressively as they want to.”

The Red Sox have shed significantly more payroll than they’ve added this winter. In addition to their various trades, the team let Justin Turner, Corey Kluber, Adam Duvall, James Paxton, and Joely Rodríguez reach free agency; those five accounted for just over $34MM in luxury tax payroll last season. Boston’s estimated luxury tax payroll now sits below $200MM for the first time since 2020. That being the case, it’s rather surprising to hear that ownership is tightening the purse strings. After all, it wasn’t so long ago that chairman Tom Werner claimed the team would be competitive in 2024, vowing to go “full throttle in every possible way” (per Sean McAdam of MassLive.com).

Of course, this rumor may be little more than a negotiation tactic, with the Red Sox playing hard to get to drive down a free agent target’s price. However, if Breslow is serious about reducing payroll, he might look to deal Kenley Jansen or Chris Martin in the coming weeks. The veteran relievers are set to hit free agency following the 2024 season, and they’d surely draw plenty of interest on the trading block. Jansen, who is owed $16MM next year, made his fourth career All-Star team last season, while Martin, who is set to make $9.5MM, led qualified MLB relievers in ERA. Losing Jansen or Martin would be a tough blow for Boston’s bullpen, but at least one could argue the Red Sox would be selling high on either arm. Jansen will be 36 next season, and he’s no longer the dominant closer he once was. Meanwhile, Martin will be 37, and it’s highly unlikely he’ll be able to maintain an ERA below 2.00.

Breslow could also dangle Nick Pivetta, who is set to earn approximately $6.9MM in his final year of arbitration eligibility, but then again, the team’s rotation looks thin enough as it is. Finally, the chief baseball officer would surely wish to be freed of the $95MM remaining on Trevor Story’s contract, but it’s hard to imagine the Red Sox could find a trade partner willing to take on the injury-prone shortstop.

It should also be said that it’s unclear which player Cotillo’s report refers to, as the Red Sox has been connected with no shortage of top free agents. The list includes frontline starting pitchers Blake Snell and Jordan Montgomery, high-end relievers Jordan Hicks and Robert Stephenson, and slugging outfielder Teoscar Hernández. All five of those free agents will be rewarded handsomely this winter, but needless to say, some will command a much higher salary than others. Perhaps the Red Sox would need to shed payroll before signing any of these players, but it’s possible they would only need to cut back to sign Snell or Montgomery to a nine-figure deal.

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