Tarik Skubal, Kyle Tucker and the Next 10 MLB Players to Sign $250 Million Contracts
In each of the past four Major League Baseball offseasons, at least $3 billion was spent on free agents, most notably on Juan Soto, Shohei Ohtani and Aaron Judge. Those mega deals came in addition to the gargantuan extensions signed by the likes of Vladimir Guerrero Jr., Francisco Lindor and Bobby Witt Jr.
So, who's on deck for the next long-term contract with a face value of at least a quarter-of-a-billion dollars?
In years past, the threshold for this article was $100 million contracts. But nine figures just doesn't go as far as it used to, does it? There are 68 players already operating on contracts of $100 million or more, and there could be a dozen more getting handed out to free agents this winter.
These days, $250 million is the new $100 million, with fewer than 20 players signed to deals of that magnitude, representing the truly elite talents who teams are hoping will be the highly productive face of the franchise for a decade or longer.
After an initial tier of fringe candidates, the top 10 are presented in alphabetical order.
12 Honorable Mentions
1 of 11
Ronald Acuña Jr., OF, Atlanta Braves
Will turn 31 shortly after reaching free agency after 2028 season
Atlanta locked Acuña in long ago on an eight-year deal with club options to extend it to a full decade. He won't be available again until after his age-30 campaign. But if he has a mostly clean bill of health for the next three years, it's not outlandish to think he could sign another eight-year deal at north of $30 million apiece.
Roman Anthony, OF, Boston Red Sox
Will be 30 when he reaches free agency after 2034 season
See: Ronald Acuña Jr. Boston bought out Anthony's 20s on a big extension shortly after his arrival in the big leagues, but it's plausible he could get a second, even bigger contract if he ends up making this one look like a laughably team-friendly deal over the course of the next decade.
Riley Greene, OF, Detroit Tigers
Will have just turned 28 upon reaching free agency after 2028 season
Greene has slowly but surely blossomed into a real star, going for 36 home runs and 111 RBI during an age-24 campaign in which he was healthy enough to play in darn near every game. The AL-high 201 strikeouts stands out as a concern, but Kyle Schwarber, Shohei Ohtani and Cal Raleigh all landed in the 187-197 range without anyone much caring. If he stays healthy and continues to mash, he could become a quarter-billionaire in a few years' time.
Jackson Holliday, 2B, Baltimore Orioles
Will turn 27 shortly after reaching free agency after 2030 season
Holliday has yet to live up to the hype of being the unanimous best prospect in baseball heading into the 2024 campaign, but let's remember he also couldn't legally drink a Natty Boh 11 months ago and has five years left to figure things out before reaching free agency at what will still be an uncommonly young age. We'll see if he gets there, though. If the O's are savvy, they'll try to "buy low" on his modest start with something like an eight-year, $150 million extension this winter. Even if that happens, though, he'd still only be 30 when the time comes for that second contract.
Munetaka Murakami, 3B, Yakult Swallows
Turns 26 in February, expected to be posted this winter
We'll find out soon enough if anyone is willing to go as high as $250 million for a player who strikes out quite a bit and is generally regarded as a defensive liability. But Murakami is 100 days younger than Juan Soto was one year ago, and opportunities to sign young sluggers simply don't grow on trees. The bidding war here could get wild.
The 'Shortstops Always Get Paid' Tier
CJ Abrams, SS, Washington Nationals
Will turn 28 just before reaching free agency in three years
Zach Neto, SS, Los Angeles Angels
Turns 29 a few months after hitting free agency following 2029 campaign
Jeremy Peña, SS, Houston Astros
Will turn 30 just before reaching free agency in two years
Masyn Winn, SS, St. Louis Cardinals
Will be 27 when he hits free agency after 2029
Of the 18 players currently on contracts of greater than $275 million, six are shortstops: Bobby Witt Jr., Francisco Lindor, Trea Turner, Xander Bogaerts, Corey Seager and Mookie Betts. (Yes, Betts was a RF when he signed his $365 million deal, but that just means he swaps spots with current RF Fernando Tatis Jr., who was a SS when he signed his $340 million contract.)
Of this quartet of fringe candidates for $250 million, Peña would be the likeliest candidate if he wasn't the eldest statesmen. Even so, Turner was 29 when he signed his $300 million contract, while Bogaerts was already 30 when he got $280 million, so never say never.
Abrams is probably too much of a defensive liability to make the grade here, but after three consecutive seasons with at least 18 home runs and 31 stolen bases, a similar three-year run to free agency could net him a whole lot of money.
The 'Sometimes Aces Get Megadeals' Tier
Hunter Brown, RHP, Houston Astros
Will be 30 when he reaches free agency after 2028 campaign
MacKenzie Gore, LHP, Washington Nationals
Turns 29 a few months after hitting free agency following 2027 season
Eury Pérez, RHP, Miami Marlins
Will be 26 when he hits free agency after 2029
The two pitchers who are going to be named the 2025 Cy Young winners in the coming weeks will appear in the top 10 as just about guaranteed candidates to join Gerrit Cole and Yoshinobu Yamamoto in MLB's club of extremely well-compensated pitchers. But here are three others who figure to be headed for nine-figure deals when they reach free agency.
The fun side of Pérez making his MLB debut at just 20 years old is that his age-27 seasons and beyond will be up for grabs in free agency. He had a few duds in his return from Tommy John surgery this season, but he also ended the year by striking out 26 of his final 55 batters faced and will have four more years to build his value.
Junior Caminero, 3B, Tampa Bay Rays
2 of 11
Age/Contract: Turned 22 in July, will hit free agency in five years
2025 Production: .264/.311/.535, 45 HR, 110 RBI
While Cal Raleigh, Kyle Schwarber, Shohei Ohtani and Aaron Judge all racked up at least 53 home runs in 2025, Junior Caminero kind of quietly mashed his way to one of the most impressive age-22-or-younger seasons of all-time.
We're talking "one of just five players ever with at least 45 home runs" impressive, and the other four on that list are Hall of Famers Joe DiMaggio, Eddie Mathews and Johnny Bench and Toronto's $500 million man Vladimir Guerrero Jr.
Caminero does need to answer some questions before we start really trying to forecast what size contract he could fetch half a decade from now.
For starters, is his glove/range good enough to stay at third base long term?
Among the 35 players to log at least 800 innings at the hot corner over the past two seasons, Caminero's .942 fielding percentage ranks dead last. And he was considerably worse than that in the minors (.907), so we'll see if he's improving or if he's doomed for some negative regression.
Also, how much of his great season was simply a product of playing at Steinbrenner Field? He did hit one more home run on the road (23) than he did at home (22), but his OPS at home (.954) dwarfed his mark on the road (.743). Caminero also had a 1.352 OPS in the three games played at Sutter Health Park, if we're questioning his ability to hit outside of Triple-A venues in general.
All the same, his breakout year was no surprise. Caminero was a unanimous top-five prospect heading into 2024, and he could end up being an even better "for average" hitter than he showed this season, batting .307 in four minor league seasons before posting a tough-luck .260 BABIP this season.
Pete Crow-Armstrong, CF, Chicago Cubs
3 of 11
Age/Contract: Turns 24 in March, will hit free agency in five years
2025 Production: .247/.287/.481, 31 HR, 95 RBI, 35 SB
Did you know there were seven players who went 30/30 this season?
Juan Soto's quest for 40/40 (finished at 43/38) was well-documented, but we also had José Ramírez (30/44), Corbin Carroll (31/32), Francisco Lindor (31/31), Jazz Chisholm Jr. (31/31), Julio Rodríguez (32/30) and Pete Crow-Armstrong join what used to be a relatively exclusive club. (No one did it in 2022, and only Cedric Mullins, with 30 of each, pulled it off in 2021. All hail the bigger bases, pitch clock and disengagement rules.)
After his sensational start to this season, though, it ended up being disappointing that PCA only got to 31 and 35, didn't it?
He was at 25 homers and 27 steals by July 10 before managing just six and eight, respectively, and batting .209 over his final 65 games.
So, which is the real Crow-Armstrong?
We know darn well he is an elite defender, quite possibly headed for the NL's Platinum Glove if those voters are willing to overlook Patrick Bailey's otherworldly Fielding Run Value. At the very least, PCA is going to secure the first of what should be many Gold Gloves.
But whether he's an elite center fielder who consistently bats like Julio Rodríguez or like Myles Straw over the next few years is going to dictate whether he gets paid accordingly.
Considering he hit .295 and slugged .515 in the minors, the inclination is to believe the first 92 games were more legitimate than the latter 65. If so, the current Cubby who will be 28.5 years old if and when he gets to free agency at the end of 2030 will be gearing up for a mammoth payday.
Elly De La Cruz, SS, Cincinnati Reds
4 of 11
Age/Contract: Turns 24 in January, will hit free agency in four years
2025 Production: .264/.336/.440, 22 HR, 86 RBI, 37 SB
Elly De La Cruz was one of just six players to appear in at least 162 games in 2025, this after also tallying 160 games played in 2024. However, between a reported quad injury and the inherent difficulties of trying to carry that Reds offense basically by himself, he simply was not the same player in the second half.
De La Cruz had 18 home runs, 22 stolen bases and an .861 OPS through Cincinnati's first 84 games compared to four, 15 and .688, respectively, from June 30 onward.
Even so, he will enter 2026 as one of the most feared hitters and maybe the singular most dangerous baserunner in the game today. If he were hitting free agency right now, he legitimately could surpass Juan Soto's record $765 million contract on what would essentially be a lifetime deal.
Without making any effort to account for inflation over the next four years, he easily could be headed for a $500 million contract when he does become a free agent after 2029.
The one big question, though, is whether he'll remain a shortstop, and where his home in the field will be if he doesn't.
De La Cruz committed an MLB-high 29 errors in 2024 before also "leading" the majors with 26 this past season. That's 55 total while no one else has even reached 40 during that time. And it's because the similarly physically-gifted Oneil Cruz has become such a defensive liability that he wasn't even deemed an honorable mention here.
EDLC should still get $250 million with room to spare, though. The glove issue really just raises a question of how far beyond that threshold teams will be willing to go.
Gunnar Henderson, SS, Baltimore Orioles
5 of 11
Age/Contract: Turned 24 in June, will hit free agency in three years
2025 Production: .274/.349/.438, 17 HR, 68 RBI, 30 SB
Gunnar Henderson missed most of spring training and the first seven games of the regular season with an intercostal strain and never did quite reharness his usual power stroke, ending the season with less than half as many home runs as he hit in 2024 (37).
Nevertheless, you can just about count on one hand how many position players have been more valuable than he has been over the past three years. At any rate, the only others with at least 80 home runs and 60 stolen bases since the beginning of 2023 are Shohei Ohtani, Francisco Lindor, Julio Rodríguez, Bobby Witt Jr. and José Ramírez.
While those five are each making north of $20 million per year on their long-term contracts, though, Henderson is only now arbitration-eligible for the first time after three consecutive years of making less than $800,000.
But this is where Baltimore really starts to pay for not paying him sooner. Henderson will likely end up making north of $40 million across his three arbitration years before possibly signing a $500 million contract once he hits the open market, provided he continues to produce at anywhere near the same level as he has so far.
Nick Kurtz, 1B, Athletics
6 of 11
Age/Contract: Turns 23 in March, will hit free agency in five years
2025 Production: .290/.383/.619, 36 HR, 86 RBI
Everyone else on this list had at least some MLB experience prior to 2025, but Nick Kurtz was the rookie sensation who ended up being the only player aside from Aaron Judge and Shohei Ohtani with at least 450 plate appearances and an OPS north of 1.000.
Playing home games in the Triple-A launching pad known as Sutter Health Park certainly didn't hurt his stats, but Kurtz even hit .291/.385/.582 on the road, including that preposterous trip to Houston in which he went 11-for-15 with four home runs.
Kurtz does have a high whiff rate, though, striking out in nearly 31 percent of his trips to the plate. Then again, Judge struck out in 31.6 percent of plate appearances in his first four years in the majors, and he has panned out pretty nicely, no?
We'll see where things go from here, as Kurtz has a long wait until reaching free agency. But in the past 90 years, the only rookies to hit more home runs than Kurtz were Judge, Pete Alonso, Mark McGwire, Cody Bellinger, Albert Pujols and Frank Robinson—a fact which becomes even more ridiculous when you consider Kurtz only played in 117 games.
The A's signed Lawrence Butler to a seven-year, $65.5 million extension after his impressive rookie campaign in 2024, but good luck trying to lock in Kurtz at a similar rate this winter.
Wyatt Langford, OF, Texas Rangers
7 of 11
Age/Contract: Turns 24 in November, will hit free agency in four years
2025 Production: .241/.344/.431, 22 HR, 62 RBI, 22 SB
Most of the players on this list will probably need to sign with a new team in order to sniff a $250 million contract, but Wyatt Langford becoming a Texas Ranger for life is plausible.
They presently have Corey Seager, Marcus Semien, Jacob deGrom and Nathan Eovaldi each on a contract with an AAV of at least $25 million, but Seager's is the only one that goes beyond 2028. Thus, by the time Langford hits his final year of arbitration eligibility—if they don't extend him before then—Texas could be sitting on quite the pile of spending money and ready to invest in another face of the franchise.
And it might not be much longer before Langford proves he deserves to be that well-compensated star.
He has already been solid, racking up at least 200 total bases in each of his first two years in the majors. He was also named a finalist for the AL Gold Glove among left fielders. (Though, it's probably going to go to Steven Kwan.)
But the No. 4 overall pick in the 2023 draft is still just warming up, if his pre-MLB stats are any indication.
Langford hit .363 with a 1.217 OPS in his three years at the University of Florida. He proceeded to hit .360 with a 1.157 OPS while skyrocketing through the minors the fall after he was drafted. And there were multiple month-long stretches in both 2024 (June and September) and 2025 (April and August) where he showcased that supernova potential.
Once he figures out how to shine more consistently, look out.
Paul Skenes, RHP, Pittsburgh Pirates
8 of 11
Age/Contract: Turns 24 in May, will hit free agency in four years
2025 Production: 187.2 IP, 1.97 ERA, 0.95 WHIP, 10.4 K/9
In MLB history, there have been just nine instances of a pitcher meeting all four of these criteria: at least 130 IP, at least 10.0 K/9, ERA of 2.00 or lower and WHIP of 1.00 or lower. Those instances were Goose Gossage in 1977, Pedro Martínez in both 1997 and 2000, Clayton Kershaw in both 2014 and 2016, Blake Snell in 2018, Jacob deGrom in 2018 and Paul Skenes in each of the past two seasons.
Skenes was named NL Rookie of the Year last season and will soon be announced as the winner of the NL Cy Young award, despite winning just 10 games for a last-place Pirates team that couldn't hit its way out of a paper bag.
Already, there is a growing and almost irrefutable narrative this his greatness is being wasted on a team that isn't serious about winning.
The Angels never won anything with Mike Trout and Shohei Ohtani together for six years, but at least they tried, taking big swings in free agency and consistently ranking top 10 in payroll.
Meanwhile, Pittsburgh's big offseason move after Skenes' sensational rookie year was bringing in 34-year-old Andrew Heaney and 37-year-old Tommy Pham in late February, after the entire league had already told them "thanks but no thanks."
Eventually, though, he'll get out of Pittsburgh and will probably end up signing the biggest contract ever for a pitcher (aside from Ohtani).
Tarik Skubal, LHP, Detroit Tigers
9 of 11
Age/Contract: Turns 29 in November, will hit free agency next winter
2025 Production: 195.1 IP, 2.21 ERA, 0.89 WHIP, 11.1 K/9
Since the beginning of 2023, Tarik Skubal has made 77 regular-season starts with a 2.39 ERA, 0.90 WHIP and 11.0 K/9, with an additional six postseason starts featuring marks of 2.04, 0.73 and 12.7, respectively.
Simply put, he has been masterful, putting up numbers that are almost as outrageous as what Pedro Martínez did in his four-year peak from 1999-2002 (2.07 ERA, 0.87 WHIP, 12.0 K/9).
And in case you haven't heard, Detroit's attempts to extend Skubal in advance of what will be his final season before reaching free agency have not gone well at all. The New York Post's Jon Heyman reported a week ago there's a continental divide of $250 million separating the two sides in negotiations.
For the time being, the all-time largest contract for a pitcher (again, aside from Shohei Ohtani) is the $325 million deal the Dodgers gave Yoshinobu Yamamoto two winters ago.
But if Skubal were hitting free agency right now, fresh off what will surely be a second consecutive Cy Young award, he'd probably fetch something in the vicinity of a 10-year, $400 million deal. Hard to blame him for insisting the Tigers pay him accordingly in order to lock him up now and prevent him from getting to free agency, like the Blue Jays did with Vladimir Guerrero Jr. this past April.
The big question until further notice is whether Skubal will get traded one year before his massive payday, a la Corbin Burnes leaving Milwaukee for one year in Baltimore before signing his $210 million contract with Arizona.
Kyle Tucker, OF, Chicago Cubs
10 of 11
Age/Contract: Turns 29 in January, Free Agent this offseason
2025 Production: .266/.377/.464, 22 HR, 73 RBI, 25 SB
For a hot minute this summer, there was talk of Kyle Tucker getting at least $500 million this offseason.
He had already been a borderline top-10 player in the majors for the half-decade leading up to this season, and he was putting up MVP-caliber numbers through the first half of the season, ending June batting .291 and on pace for 33 home runs, 102 RBI and 39 stolen bases.
For the second straight season, though, Tucker's sensational first half was derailed by a June injury.
He missed three months in 2024 after fouling a pitch off his shin. This year, he played through a hairline fracture in his hand before missing most of September due to a calf strain. And from July 1 onward, he managed just a .690 OPS in 53 games played, limping into what will still be a very lucrative free agency, even if the $500 million ship has perhaps sailed at this point.
Spotrac presently puts Tucker's market value at 10 years, $402 million. Could see that swinging $100 million in either direction, but the four-time All-Star who has played in the postseason in every year of his career thus far will surely eclipse a quarter-billion as the crown jewel of this winter's crop of free agents.
James Wood, OF, Washington Nationals
11 of 11
Age/Contract: Turned 23 in September, will hit free agency in four years
2025 Production: .256/.350/.475, 31 HR, 94 RBI, 15 SB
In Stephen Strasburg, Anthony Rendon, Bryce Harper, Trea Turner and Juan Soto, the Washington Nationals sure have had a lot of talent come through their farm system before signing contracts well north of $200 million in free agency.
And though he has a long way to go before reaching the open market, James Wood is on the fast track to becoming the next member of that club.
Whether this will be the one that actually stays with and pans out for the Nats remains to be seen, but the potential for greatness is clearly there.
Well, at least it was early in the year.
First 92 games: .939 OPS, 26.5 K%, 162-game paces of 42 HR, 122 RBI and 21 SB
Rest of season: .666 OPS, 40.1 K%, 162-game paces of 17 HR, 62 RBI and 7.5 SB
Whether the Home Run Derby messed up his swing or he simply hit a wall in mid-July, Wood devolved from hitting like Shohei Ohtani to whiffing like Patrick Wisdom, striking out 20 more times (221) than the next-closest player, and falling just two Ks shy of matching Mark Reynolds' single-season record of 223.
If that's his new normal, he'll be lucky to get a $25 million contract one day, let alone $250 million. But if he can get back to playing like one of the 10 best players in the world, the sky's the limit for this 6'7" slugger.
