Which MLB Free Agent Left Will Get the Longest Deal?
Some marquee names still remain free agents. Which of the available players will receive the longest contract?

Spring Training is nearly upon us, and some of baseball’s most notable free agents still remain without a home for the 2025 season.
Coveted bats such as Pete Alonso and Alex Bregman went into the offseason with the hopes of receiving a luxurious long-term contract. However, their markets haven’t materialized as they anticipated over the past few months.
Given the significant shift in demand for some of baseball’s top remaining free agents, some players may have to pivot and settle for a shorter contract as a result.
These shorter, high-AAV contracts have become quite popular in recent seasons.
They’ve been especially prevalent for talented players who come with some degree of concern. They’re a nice fallback option if a player doesn’t receive the long-term deal that they desired, and we saw several of MLB’s biggest free agents agree to this style of contract last offseason.
Blake Snell, the reining Cy Young winner at the time, didn’t receive the long-term commitment that he was looking for last offseason. Instead, he signed a two-year, $62 million deal with the San Francisco Giants. The deal included a player opt-out following the 2024 season.
Snell put together another strong year on the mound this past season, pitching to a 3.12 ERA to go with a 2.43 FIP, and re-entered free agency after opting out of his contract with the Giants earlier this offseason.
Just a few weeks later, Snell reached a five-year, $182 million deal with the Los Angeles Dodgers, rewarding him with the long-term agreement he was previously searching for.
Another example from last offseason is Matt Chapman, who signed a three-year, $54 million contract (including opt-outs following the 2024 and 2025 season) with the Giants after reportedly originally seeking a deal close to $200 million.
Chapman put together a strong 2024 campaign, and in September, San Francisco rewarded him with a six-year extension worth $151 million. He finally earned the contract he should have already gotten in the preceding offseason with his strong play just a few months after signing with his new ball club.
Exchanging contract length for a higher AAV on a shorter contract might not seem like an immediate win, but these type of agreement structures can still pay off in the long run. It doesn’t always work out, but it may be some of the remaining free agent’s best options at this point.
Let’s take a look at which of the top remaining free agents still have a shot at a long-term agreement, and which may have to pivot to a shorter agreement.
RHP Jack Flaherty, 29
Clearly the top free agent starting pitcher remaining, Flaherty boosted his value in a big way in 2024. He dazzled in his time with the Tigers before being traded to the Dodgers, where he would eventually be the Game 1 starter in the World Series for the World Champions.
He’s plenty talented when healthy, but Flaherty’s track record is likely giving some organizations pause before inking him to a long-term deal. While his 2024 season was quite impressive, the years that came before that weren’t quite as encouraging.
Back in 2019, Flaherty was looking like an up-and-coming ace of the league, finishing fourth in NL Cy Young voting after throwing a career-high 196.1 innings and ending the season with a 2.75 ERA (152 ERA+) and a WHIP under 1.00.
What he did after that season was a far cry from that level of production. In his four seasons from 2020-2023, Flaherty threw just 299 total innings and pitched to a 4.42 ERA (94 ERA+) with a WHIP near 1.40.
Diminished pitch command and strikeout material was the big discrepancy between those two versions of Flaherty.
In 2019, he ended the year with a strikeout rate of 29.9% and a walk rate of 7.1%. From 2020-’23, his strikeout rate dropped to 24.1% while his walk rate rose nearly three percent.
In 2024, however, Flaherty returned to form, matching his career-high in strikeout rate from 2019 (29.9%) and walking fewer than six percent of batters, which was his career-best.
So, how does an organization value a pitcher who is clearly capable of pitching on the biggest stage and has tons of ability, but has a rather inconsistent track record?
The answer to that question is likely why he has yet to find a home for the 2025 season.
Perhaps here is where Flaherty could elect to sign a deal similar to that of Snell or Jordan Montgomery from an offseason ago (Montgomery signed a one-year, $25 million deal with a vesting option in year two with the Arizona Diamondbacks).
If Flaherty does sign a contract of this structure, he could re-enter free agency at age 30 and still earn the long-term contract he desires, just as we saw Snell do this offseason. It may be his best option if he’s not receiving the type of interest he initially anticipated.
OF Anthony Santander, 30

Last week for Just Baseball, I broke down how the deal that Teoscar Hernández signed with the Dodgers likely set the market for Santander.
Hernández signed a three-year deal worth $66 million, and the eventual deal that Santander signs could end up being very similar to that in terms of AAV. The big question is whether or not he will receive the fourth or fifth year that he is seeking.
Santander deserves to be compensated for the season that he had in 2024. He was one of the top power bats in the sport and one of the most prolific run producers in MLB. However, there are aspects to his player profile that make him a risky long-term investment for a ball club.
Because of that, his market hasn’t materialized as he anticipated over the course of the winter.
In fact, it was recently reported by Ken Rosenthal and Will Sammon of The Athletic that Santander (and Flaherty) are considering short-term contracts at a high AAV. While this would likely be a last resort for Santander, a deal of this structure with player opt outs could have some benefits.
If Santander were to sign a shorter, high-AAV contract that includes player opt outs, this would give him more earnings up front while still allowing him to re-enter free agency in the near future.
If things go well for him in 2025, he could then be able to earn the long-term contract he was originally seeking.
The Blue Jays seem like the most likely landing spot for Santander at this point, and it’s yet to be seen if they’re willing to give him the contract length he’s looking for given the current state of the organization.
Toronto is going for it in 2025, and Santander would be a big boost for their offense. But with Bichette and Guerrero Jr. set to hit free agency following the season, a shorter deal with player opt outs could make more sense for the Blue Jays if Santander is open to this type of option.
1B Pete Alonso, 30
Alonso’s market dried up rather quickly this offseason. After heading into free agency as one of the top offensive weapons available, he still remains a free agent with his list of potential suitors getting shorter and shorter.
Many teams were expected to be in on the Alonso sweepstakes heading into the offseason. But fast forward to the middle of January, and many of those teams have already addressed the first base position.
Christian Walker signed a three-year, $60 million deal with the Houston Astros. Paul Goldschmidt inked a one-year, $12.5 million contract with the New York Yankees.
Carlos Santana and Josh Bell each signed one-year deals with the Cleveland Guardians and the Washington Nationals, respectively. And the Arizona Diamondbacks swung a trade for Josh Naylor to replace Walker at first base.
While Alonso is clearly the top first baseman left on the open market, the lack of demand makes it far less likely he receives the hefty price tag that he’s asking for.
For a while, the New York Mets were the clear-cut option to land Alonso on this type of short-term, high-AAV contract. However, more recent reports indicate that there is still a financial barrier between the two parties, and the Mets might be preparing to head into 2025 without their long-time slugger.
If the Mets are indeed out of the picture, not only does that take away a top landing spot for Alonso, but there aren’t many teams remaining who are likely to match his alleged price point.
It’s been a fascinating offseason for the Polar Bear, and the path forward appears unclear for both where he will end up and the type of contract he’ll settle on.
3B Alex Bregman, 30
Bregman appears to be the most likely to ink a long-term deal. He’s had three consecutive seasons with an fWAR above 4.0, and he’s never finished with ain OPS+ below 113 in his nine-year career.
His ability might not be at the level it was back in 2018-’19 when he finished top five in MVP voting in back-to-back seasons, but he’s still a very talented player with plenty of demand on the open market.
However, negotiations with Bregman have stalled in recent weeks. Teams have flashed interest in the 30 year old, but it appears as if organizations are getting cold feet on offering him the substantial deal he is seeking.
If Bregman isn’t getting the deal he believes he deserves and shifts his sights to a shorter deal with an opt out after year one, perhaps his list of potential landing spots increases, boosting his demand.
Boston and Detroit have long been linked to Bregman, but both clubs appear apprehensive to lock down their third base position for such a long period of time.
Being a client of Scott Boras, who famously orchestrated the short deals with opt-outs last offseason, there’s a good chance the same negotiations are happening this winter with Bregman.
Remember, Cody Bellinger – a client of Scott Boras – also went into last offseason reportedly seeking a deal near $200 million. He eventually settled on a three-year, $80 million contract with an opt-out after 2024, which he did not exercise given his lackluster performance last season.
Bellinger was younger and had more of an uncertain track record than Bregman, so it’s not exactly an apples-to-apples comparison. However, it does shed light on how these negotiations can evolve over the course of an offseason, especially for Boras clients.
Dark Horse Candidate

Players such as the ones listed above have grabbed most of the recent attention in free agency, but there is one player flying under-the-radar who could end up signing the longest deal of them all.
Southpaw reliever Tanner Scott, 30, has been sensational over the course of his last two seasons.
From 2023-’24, Scott leads all MLB relievers in fWAR at 4.5. Over that stretch, he’s fourth in ERA (2.03) and fifth in FIP (2.53). What’s more, Scott does it all on the mound.
In his last two seasons, he’s kept the ball in the park with an impressive HR/9 of 0.36, he’s struck out a whopping 11.28 hitters per nine innings, and he’s generated a ground ball rate north of 50%.
He’s also been one of the most available relief pitchers in the sport since 2023, tossing 150 innings, which is the fourth-most in MLB among relievers. He earned the first All-Star bid of his career in 2024, on the back of a 1.75 ERA in 72 innings pitched.
While Scott’s track record prior to 2023 isn’t quite as ideal, his level of production and efficiency over his impressive body of work recently should warrant a long-term contract, and it could end up being the longest of the remaining free agents.
Scott is reportedly seeking a four-year, $80 million offer ($20 million AAV), and it seems like there are teams willing to pay that price.
When looking at the recent landscape of reliever contracts, Edwin Diaz signed his five-year, $102 million agreement two offseason ago at age 28. Josh Hader signed his five-year, $95 million deal last winter at age 29. It feels as if a four-year deal for Scott feels exactly right given the current reliever market.
So far this offseason, among top-end relievers signed thus far, Clay Holmes inked a three-year, $38 million deal with the Mets, but his situation is a bit different since he’s going to be tried as a starter. Likewise, Jeff Hoffman recently agreed to a three-year, $33 million contract with the Blue Jays, and Scott is a superior closer to Hoffman, and two years younger.
Point being, could Scott be the one player remaining in free agency to earn himself a guaranteed four-year contract? At this point in time, it’s a real possibility.
We’ll see how things unfold in the coming weeks as teams gear up for Spring Training, but there’s still plenty of time remaining in the offseason for some of baseball’s biggest dominoes to fall.