Spring training is fast approaching and so is extension season. Generally speaking, MLB teams use November, December, and January to improve their roster. In February and March, they shift their focus to retaining their own players. Count on more than a few players forgoing free agency and signing a long-term extension between now and Opening Day.
Among the players who signed long-term extensions last spring were Bobby Witt Jr. (11 years, $288.8 million), Mitch Keller (five years, $77 million), Ezequiel Tovar (seven years, $63.5 million), and Brayan Bello (six years, $55 million). Ceddanne Rafaela (eight years, $50 million) signed his extension soon after Opening Day. Expect more to follow suit this spring.
With that in mind, let’s take a look at this spring’s top long-term extension candidates. Here are 10 notable extension candidates, listed alphabetically.
A year ago, Caminero was arguably the best prospect in baseball, and he showcased his hard-hit ability and prenatural feel for contact after the Rays called him up for good in August. Caminero is still only 21 and he is one of the most promising young hitters in the game. The Rays have a history of locking up their top players before they reach even one full year of service time (Wander Franco, Evan Longoria, Matt Moore, etc.). Surely they’ll try to do the same with Caminero.
One possible issue: The Rays do not have a long-term home. They will play 2025 at George M. Steinbrenner Field, a Single-A ballpark in Tampa. Where they’ll play in 2026 and beyond, we do not know. The Rays and the city of St. Petersburg are haggling over the repairs of Tropicana Field and taxpayer dollars for the team’s proposed new stadium. Caminero could jump at the long-term security and sign despite the ballpark precariousness. It would be understandable if that uncertainty gave him pause though.
Possible extension: The largest contract given to a player with less than one full year of service time is the 12-year, $210 million deal the Mariners made with Julio Rodríguez. He signed that contract in August of his rookie season, after being an All-Star and emerging as the overwhelming favorite to win Rookie of the Year. Caminero is good, but Rodríguez was more established at the big-league level and thus had more leverage in contract talks. A Julio contract is out of reach for Caminero.
A more appropriate contract benchmark is Corbin Carroll’s eight-year, $111 million contract with the Diamondbacks. Like Caminero, Carroll was considered one of the top prospects in baseball at the time, and his MLB experience at the time of the signing was minimal (32 games). Adjust upward to account for two years of inflation, and eight years and $120 million or so could work for Caminero. That would give the Rays two additional years of control beyond the standard six.
The Red Sox traded a handsome package that included their last two first-round picks (Kyle Teel and Braden Montgomery) to get Crochet from the White Sox in December. The 25-year-old is the ace the Red Sox have lacked since Chris Sale was in his prime, and the two sides have discussed an extension in recent weeks. Crochet will be a free agent after the 2026 season, so while an extension isn’t an urgent matter, it is something the Red Sox would like to get done sooner rather than later.
“There have been conversations with my agent and the front office, just kind of getting a feel for one another,” Crochet said earlier this month (via MassLive.com). “Staying in Boston long-term is something that has a lot of merit in my mind and something I think would be awesome. In the meantime, I’m just focusing on spring and getting ready for the upcoming season, trying to stay focused one day at a time. When something’s presented, then we’ll attack it.”
Possible extension: Crochet’s situation is almost unprecedented. He began his career as a reliever, missed all of 2022 and most of 2023 with Tommy John surgery, then he transitioned to the rotation and was an All-Star in 2024. That is not the usual career path and could make finding common ground on an extension tricky. Crochet will want to be paid like an ace starter. The Red Sox will want to bake a little protection into the contract in case he gets hurt again, or winds up back in the bullpen down the line.
Crochet and the Red Sox avoided arbitration with a $3.8 million contract earlier this month. A six-year extension that pays him $10 million in 2026 (his final arbitration year) and then $25 million annually from 2027-31 (free agent years) would total $135 million. Add in a signing bonus and the buyout of an option year, and they could push the guaranteed money to $150 million. For reference, the Twins signed Pablo López to a four-year, $73.5 million extension when he was at the same service time level as Crochet. We’re tacking two years and $60-plus-million on top of that.
Earlier this month, the Cardinals and Donovan were unable to reach a 2025 contract agreement before the arbitration salary filing deadline. He filed for $3.3 million, the team for $2.85 million. Filing salary figures does not mean they are locked into an arbitration hearing. The two sides could still discuss and agree to a contract of any size prior to a hearing, including a long-term extension. Donovan, 28, has three years of team control remaining, and will become a free agent after the 2027 season.
Somewhat surprisingly, the Cardinals and Donovan had minimal talks about a multi-year extension before the filing salary figures, reports MLB.com. Donovan hoped for a long-term deal, but the Cardinals didn’t show much interest. Does that mean St. Louis is content to go year-to-year with Donovan? Perhaps, though these things can change with one phone call. The Cardinals, it should be noted, have not signed a position player to a long-term deal that buys out free-agent years since Paul DeJong in 2018.
Possible extension: The Padres signed Jake Cronenworth to seven-year extension worth $80 million when he was at Donovan’s service time level a few years ago. That’s a pretty solid contract benchmark for Donovan. If the Cardinals prefer something shorter term, a three-year contract that buys out Donovan’s arbitration years but no free-agent years could be the sweet spot. That would give Donovan security and the Cardinals cost certainty over his arbitration years. Does $3 million in 2025, $6 million in 2026, and $10 million in 2027 for a total of $19 million do the trick?
The Mariners have four extension-worthy starting pitchers. We’re listing Gilbert here rather than George Kirby, Bryce Miller, and Bryan Woo simply because he is closest to free agency. Gilbert will become a free agent after the 2027 season, Kirby after 2028, and Miller and Woo both after 2029. The Mariners and Gilbert avoided arbitration with a $7.625 million contract earlier this month. In October, the Seattle Times reported the two sides had yet to discuss an extension, though October is an unusual time for extensions talks. Those typically wait until the spring.
Under GM Jerry Dipoto, the Mariners have a long history of extending players prior to free agency, with Luis Castillo, J.P. Crawford, Andrés Muñoz, and Julio Rodríguez all signing long-term deals during their team control years. Gilbert is a pitcher and pitchers get hurt — he’s not oblivious to that — which could create some urgency on his side to get a done deal. He has been very durable as a big-league pitcher, though durability can disappear quick. Three years until free agency is an eternity in this sport.
Possible extension: Gilbert is a Super Two, meaning his service time level will allow him to go through arbitration four times rather than the usual three. His 2026 and 2027 salaries will be higher than the typical All-Star starter approaching free agency, and those increased salaries must be reflected in an extension. Gilbert, 28 in May, is in a unique situation, unique enough that not a single Super Two starting pitcher three years away from free agency has signed a long-term extension since at least 2007.
Similar to Crochet, we’ll have to suss out a potential Gilbert extension from scratch, with no recent reference points. How does this sound: $12 million in 2026 (third arbitration year), $17 million in 2027 (fourth arbitration year), then $27 million per year from 2028-30 (free-agent years). That’s five years and $110 million covering 2026-30. The $27 million per free agent year is Tyler Glasnow/Max Fried money. A signing bonus and option buyout can push it to $125 million. Gilbert gets fewer years than Crochet because he’s two years older, but more per year because he has a cleaner injury history and a longer track record as a starter.
Up until the Anthony Santander signing, the Blue Jays were having a really hard time getting players to take their money. Guerrero is the ultimate prize for them, a homegrown star who turns only 26 in March. He will also become a free agent after the 2025 season. There is extreme urgency to get this done on the team’s part. Earlier this month, Sportsnet reported the Blue Jays and Vlad Jr. were engaged in contract talks. Obviously nothing has come of it yet, though at least they’re talking.
Guerrero has expressed an interest in staying with the Blue Jays long-term, and maybe he’ll take a discount to do so, but gosh, he sure does have a lot of leverage. The Blue Jays have struggled to land big-name free agents and Guerrero will earn more than $70 million during his arbitration years. And, of course, his father is a Hall of Famer who made over $100 million in his career. Vlad Jr. presumably does not need the money. He can play hardball in a way most players can’t. The Blue Jays and Guerrero painlessly agreed to a $28.5 million 2025 salary to avoid arbitration earlier this month.
Possible extension: I’m guessing Guerrero and his representatives have their eyes on Juan Soto’s 15-year, $765 million contract with the Mets. Guerrero is not Soto, but Guerrero having a Soto-like year in 2025 is not out of the question, plus the Blue Jays are desperate to get it done. In December, Guerrero said Toronto offered a $340 million extension that was “not even close to what we’re looking for.” That was before the Soto contract raised the bar for star players in their mid-20s.
These days, stars get signed through age 39 (Mookie Betts, Aaron Judge) or 40 (Soto, Manny Machado). That’s the magic number. To sign Guerrero through age 39, it would be a 13-year deal starting in 2026. Call it $45 million a year and that’s $585 million total. And given the leverage Vlad Jr. has over the Blue Jays, that could become 14 years at closer to $50 million per year real quick. Crazy? Yeah, maybe, though contracts for stars in their mid-20s always always wind up larger than expected. Remember, at this time last year, we were talking about Soto maybe cracking $500 million. Whatever you think Guerrero will get, take the over.
Last year’s Juan Soto trade proved to be the ultimate win-win. The Yankees got an MVP-caliber season from Soto and reached the World Series. The Padres got a high-end starter in King, the prospect they used as the headliner in the Dylan Cease trade (Drew Thorpe), plus more. King, a reliever most of his time with the Yankees, moved into the rotation late in 2023, then turned in an ace-caliber performance in 2024. He’ll look to repeat it in 2025, as he prepares to head out into free agency next offseason.
King, 30 in May, has a relatively short record as a starter, plus a funky injury history (two separate elbow fractures but no UCL damage). He wasn’t a high draft pick either (12th round in 2016). The Padres and King were unable to agree to a 2025 contract prior to the arbitration salary filing deadline earlier this month. He filed for $8.8 million while the team countered with $7.325 million. Even the lower number would exceed King’s career earnings to date by several million. Although testing free agency will surely be tempting, King might jump at the opportunity to lock in long-term security right now.
Possible extension: Tyler Glasnow signed a five-year, $136.6 million extension last offseason, when he was a year away from free agency, like King. I think that at least gets is in the ballpark for King, though Glasnow had a longer track record as a top-flight starter (and a longer injury history). The Padres convinced Joe Musgrove to take five years and $100 million three months before he was scheduled to hit free agency. Can they convince King to do the same? Might as well ask, right? Musgrove is a native San Diegan and seems to have taken a literal hometown discount though.
The Guardians managed to dump two of their pricier contracts (Andrés Giménez and Myles Straw) on the Blue Jays this offseason, freeing up significant cash long-term. Kwan has been a terrific player the last three years, and he unlocked some power in 2024. His 14 homers were three more than 2022 (six) and 2023 (five) combined. Three Gold Gloves, high batting average, and good on-base skills equal a consistent 4-WAR player with the upside for more if the newfound power production is real.
Earlier this month Kwan and the Guardians agreed to a $4.175 million salary for 2025, the first of his three arbitration years. He will become a free agent after the 2027 season, when he’ll have just turned 30. As good as Kwan is — and he is very good — corner outfielders with limited power who generate a lot of value through defense typically do not get big contracts. The Guardians paid big for defense with Giménez and dumped the contract less than two years later, and he played a premium up-the-middle position.
Possible extension: Would you believe the last full-time outfielder to sign a contract of at least four years at Kwan’s service time level was Michael Brantley in 2014? Lots of guys have signed two-year contracts that lock in some security at this service time level (Andrew Benintendi, Kole Calhoun, Adolis García, George Springer, etc.), but the last full-time outfielder who signed an extension that bought out free-agent years when they were still three years away from hitting the market was Brantley. Huh.
Anyway, the Guardians and Kwan could do something like $7 million in 2026 (second arbitration year), $10 million in 2027 (third arbitration year), and $15 million in 2028 and 2029 (free-agent years). That would be four years and $47 million, which could be easily bumped up to $50 million through an option buyout. $15 million a year for free-agent years is Andrew Benintendi money. I’m not sure the Guardians would want to go much longer than four guaranteed years (2026-29) with a corner outfielder who creates a lot of value with his defense, something that typically doesn’t age well once a player gets into his 30s.
Is it fair to say the Orioles had a disappointing offseason? I think so. That doesn’t mean it was a bad offseason, just disappointing. Corbin Burnes and Anthony Santander departed as free agents and were replaced by Charlie Morton and Tyler O’Neill. The O’s also signed Andrew Kittredge, Gary Sánchez, and Tomoyuki Sugano. Again, not bad, just a little underwhelming, especially in David Rubenstein’s first offseason as the owner. I think we all expected a big splash. Instead, the Orioles took small bites.
The vibes can shift with an extension for a homegrown player. Gunnar Henderson is a Scott Boras client and Boras likes to take his top clients to free agency. Extending Henderson might not be possible. Rutschman, who is not a Boras client, could be extendable though. He is three years away from free agency — because he finished second in the 2022 Rookie of the Year voting, Rutschman was awarded a full year of service time even though he was called up in May — and has a $5.5 million salary in place for 2025. Switch-hitting catchers with good defensive chops and leadership skills are in extremely short supply.
Possible extension: Two years ago the Braves gave Sean Murphy a six-year contract worth $73 million when he was at the same service time level as Rutschman, so there’s your contract benchmark. Murphy then was a year older than Rutschman is now, and he didn’t have the same accolades (All-Star Games, MVP votes, etc.), but that gets us in the ballpark. That contract started right away, so for Rutchman, we’re talking about looping his 2025 season into a potential six-year contract, rather than starting fresh in 2026.
A $10 million salary in 2026 (second arbitration year), a $15 million salary in 2027 (third arbitration year), and $25 million salaries from 2028-30 (free agent years) equal five years and $100 million. Loop in 2025, and it’s six years and $105.5 million. Well north of Murphy, which it should be because Rutschman is the better player and we have to account for two years of salary inflation. My guess is Rutschman and his representatives would be underwhelmed and seek closer to 10 years. That’s a lot of years for a player at the game’s most physically demanding position. It also might be the only way to keep Rutschman in Baltimore long-term.
Even before the Tigers went on their miraculous run late last year and reached the postseason, I thought the calls to trade Skubal at the deadline were crazypants. The hardest thing to acquire in this sport is a bona fide No. 1 starter. The Tigers have one, and he’s a homegrown player who came up through their system, and there is a lot of young talent around him on the roster (Riley Greene, Colt Keith, Parker Meadows, etc.). Trading Skubal at the deadline would have been insane. No, they should extend him.
Skubal and the Tigers agreed to a $10.15 million salary for 2025 earlier this month. That is a lofty $7.5 million raise from his 2024 salary ($2.65 million). Skubal won the Cy Young award though, and has been arguably the most dominant pitcher in the game since returning from flexor surgery in 2023. He will become a free agent after 2026 and is the centerpiece of a Tigers team that looks about ready to begin an extended run of contention. Locking him up long-term feels like a must for Detroit.
Possible extension: Skubal is excellent, though he also has an arm injury history, something that will be baked into the cake. The last Cy Young winner to sign an extension two years prior to free agency was Jacob deGrom back in 2019. As good as Skubal is, he is not peak deGrom. Give him $20 million for 2026 (final arbitration year) and $28 million from 2027-32 (free-agent years), and that’s a seven-year contract worth $188 million. deGrom got five years and $137.5 million six years ago. Seven years and $188 million reflects six years worth of inflation, and the fact Skubal now is three years younger than deGrom was then.
It can be safely assumed that, when they traded for Tucker in December, the Cubs did so with the intention of signing him long-term. The two sides were unable to agree to a 2025 contract prior to the arbitration salary filing deadline earlier this month, though they later hashed it out, and he will make $16.5 million this coming season. Tucker expressed interest in an extension with the Astros over the years. Does he still feel that way with the Cubs and with free agency only a few months away? The Cubs need to find out.
Chicago has very little long-term money on the books. Dansby Swanson is the only player signed beyond 2027. Shota Imanaga, who can opt out of his contract after 2025, is the only other player signed beyond 2026. The Cubs have a solid young core and top prospects on the way. Tucker is a star-caliber performer and signing him to an extension would lock in a centerpiece as the Cubbies enter what they hope is a long run of contention. Ownership and the front office have been criticized for a lack of spending the last few months. Failing to extend Tucker would only further validate the criticism.
Possible extension: Tucker is, pretty clearly, a $30 million-a-year player. He hits for average, he hits for power, he steals bases, and he’s a gifted defender. He just turned 28 too, so he’s right smack in his prime. Tucker’s representatives could ask for Aaron Judge’s contract — nine years and $360 million — and it wouldn’t be completely crazy. Judge hit 62 home runs his contract year, though he was also three years older than Tucker is now. Age is a cheat code. The younger you are, the better the contract. Teams will pay more for youth than they will for older, better players.
A contract worth $35 million a year would be the fourth-richest average annual value for an outfielder behind Juan Soto ($51 million), Judge ($40 million), and Mike Trout ($35.54 million). A 10-year contract at that salary beginning in 2026 would lock Tucker in through age 38, and come in at $350 million total. Historically, players who sign extensions one year before free agency do not take discounts. They get what amounts to a free-agent contract. Tucker just got to the Cubs and has no reason to take a “hometown” discount. The Cubs might have to go far outside their comfort zone to keep him from hitting the open market.
Read the full article here
