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.
