The MLB Teams That Must Spend Big This Offseason in Free Agency

We really have no idea what to expect from this offseason.

Will teams—knowing the owners will lock out players when the collective bargaining agreement expires on Dec. 1 at 11:59 p.m. ET—be more aggressive in the early weeks of free agency? Or will they be more cautious and wait to see what the new CBA looks like and whether it will include a salary cap?

It's hard to be certain about what this offseason will look like. But we are certain that the following teams must be aggressive in free agency.

Philadelphia Phillies

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The Phillies are always active. As they try to balance competing with an aging roster while extending their window of contention, Dave Dombrowski and company think they can do it again this offseason.

According to Spotrac, the Phillies already have $337.65 million in luxury tax commitments for the 2027 season. How much more will John Middleton's ownership group want to spend? If there is a salary cap, that could hamstring the Phillies. If there isn't, however, Dombrowski is as good as any executive in the sport's history at convincing owners to spend big money on payroll.

The Phillies have a tremendous closer in Jhoan Duran, but they badly need another elite setup man. Adrián Morejón would be a great fit if the Phillies are willing to spend big. Finding a lockdown lefty is crucial.

Additionally, with Bryce Harper returning to first base, Philadelphia needs an impact outfield bat. Randy Arozarena and Seiya Suzuki are the big fish, but Ian Happ may be a more realistic target. He has a .783 career OPS and is a four-time Gold Glove Award winner, so he could upgrade the defense of a team that finished tied for dead last in baseball, minus-51 defensive runs saved.

New York Yankees

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Aaron Judge threw down the gauntlet after the Yankees were eliminated from the playoffs regarding what the franchise needs to do to win its first World Series title since 2009.

"We're the Yankees. I feel we should go all-in and do what they need to do," Judge said. "If we got holes, if it's finding certain players or personnel, whatever we need, you got to go out there and get it. That's why I signed back here, to play with the Yankees, is to fight for a championship and go all in." 

Jon Heyman of The New York Post wrote that the Yankees executives still believe they have a strong relationship with the three-time AL MVP. They were both "somewhat annoyed" and "taken aback" by his comments.

It is perhaps a little awkward that Judge made these comments after missing both the ALWCS and ALDS with a right calf injury. As great as the eight-time All-Star has been at his peak, he played only 66 total games in 2026. One of the things the Yankees need to win is for him to stay healthy.

At the same time, Judge is the Yankees captain and gave an honest answer when asked. Also, as he heads into his age-35 season, the Yankees might be at a point where they can't plan on him being Superman anymore. Heck, even at his peak, the Yankees didn't get over the hump in October.

Some of the decisions general manager Brian Cashman will have to make this offseason will be internal. Letting Trent Grisham walk in free agency seems like an obvious move after he posted a 95 OPS+ on the qualifying offer last offseason. Will the Yankees issue a qualifying offer to Jazz Chisholm Jr. after a down year? Will they give David Bednar a lucrative multi-year deal to remain their closer? Can they count on anything from Giancarlo Stanton moving forward?

Externally, the Yankees have a great one-two punch in their starting rotation with Cam Schlittler and Max Fried, but adding another ace wouldn't hurt. Also, adding a right-handed corner infielder to pair with Luis Garcia Jr. and Ryan McMahon would make a lot of sense.

No matter what, Judge reminded Cashman that the expectation in the Bronx is always that the Yankees will be at the forefront of offseason activity.

Pittsburgh Pirates

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John Perotto of Pittsburgh Baseball Review recently wrote that Paul Skenes' salary "will be out of their comfort zone after next season." He predicted that by 2028, Skenes' second of three arbitration years, the former NL Cy Young Award winner will be on another team.

For a second, let's set aside thoughts about owner Bob Nutting and whether he should contend for control of the team if he's spooked by his franchise player's second-year arbitration salary. We know how the Pirates have operated under Nutting, so it really wouldn't be surprising if Perotto's prediction comes true.

If the Pirates feel this might be their last season with Skenes, they should step out of their comfort zone, to steal a phrase, and try to make a run. This team hasn't made the postseason since 2015. They haven't advanced a round in the postseason since winning the 2013 Wild-Card Game. They cannot let Skenes' time in the franchise pass without changing both of those.

Some of this will depend on Skenes rebounding. After winning NL Rookie of the Year in 2024 and Cy Young in 2025, Skenes posted a more modest 3.82 ERA across 174.1 innings in 2026. Both his 3.28 expected ERA and 3.33 FIP suggest he was unlucky. There's no doubt that the Buccos need the peak version of Skenes to go where they want.

Additionally, Oneil Cruz was limited to 97 games last year, while Konnor Griffin—many's favorite to win NL Rookie of the Year coming into the season—played just 80. Pittsburgh will need better health luck in 2026 as well.

But general manager Ben Cherington can't just count on internal improvements if the Pirates hope to go from 82-80 in 2026 to the postseason in 2027. His hands are often tied by ownership, but the Pirates do have some money coming off the books as Marcell Ozuna ($12 million), Brandon Lowe ($11.5 million) and Gregory Soto ($7.75 million) will all become free agents.

With Lowe hitting 35 homers and posting an .824 OPS, he's a candidate for a qualifying offer. If the Pirates extend a $23.15 million QO to Lowe, they would probably hope he rejects it and gets draft-pick compensation if he leaves in free agency. Frankly, though, that wouldn't be an unfair price to have to pay Lowe in 2027. But accepting a QO would limit ownership's willingness to spend more in the offseason.

Ultimately, much of this comes back to Nutting. Maybe he'll get what he wants this offseason with some kind of salary cap system. If not, it might be time for him to sell the team. It's not that anyone is saying the Pirates can spend as much as the Los Angeles Dodgers, but ownership in Pittsburgh has to put in a better effort.

Detroit Tigers

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It's unlikely the Tigers will make a serious move to bring back two-time defending AL Cy Young Award winner Tarik Skubal in free agency after trading him to the Dodgers this summer.

Still, Tigers baseball operations president Scott Harris needs to be active in free agency as the team looks to rebound from a disappointing 76-86 season.

Between what the Tigers had on the books for Skubal coming into the season ($32 million), and money from Gleyber Torres ($22.025 million), Jack Flaherty ($20 million) and Kenley Jansen ($11 million) coming off the books, Detroit should have some money to play with.

To some degree, how the Tigers attack the offseason will depend on what they think they have internally. Luis Arraez would be a good fit for Comerica Fifth Third Park, but Detroit may prefer to give Hao-Yu Lee extended runway at second base. Both Spencer Torkelson and Colt Keith were top prospects, but how married are the Tigers to them at first and third base, respectively?

A full season of Max Clark in center field, paired with likely AL Rookie of the Year Kevin McGonigle at shortstop, gives the Tigers an exciting young duo to build around. This team could benefit from an accomplished veteran bat joining the lineup.

Elsewhere, Detroit can hope veteran Kyle Finnegan bounces back after posting a 4.30 ERA in 63 games this past season. But think about what this bullpen would look like if the Tigers made a play for Bednar or Adrián Morejón in free agency to anchor an arm barn that also includes Tyler Holton, Drew Anderson and Jacob Waguespack.

San Diego Padres

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Here's one thing you can be sure of: A.J. Preller will always find a way to be aggressive. Perhaps more than ever this offseason, San Diego's president of baseball operations won't have a choice but to be bold.

Multiple new factors could be at play this offseason, though. First, we don't know how restrictive the new CBA will be for aggressive spenders, which the Padres have become under Preller. Second, this will be the first offseason for Kwanza Jones and José E. Feliciano as the team's owners. They seemed very invested in the club, but their willingness to spend like the late Peter Seidler did will show just how interested they are in keeping the Padres at this level of relevance.

Mason Miller still has three remaining years before free agency. He'll headline what should still be a very good bullpen with Bradgley Rodriguez, Yuki Matsui, and Wandy Peralta. However, with both Morejón and Jason Adam set to become free agents, this group could be a little more mortal in 2027.

Meanwhile, the starting rotation was already the primary area of concern for the Padres. It could become even thinner this winter.

• Michael King will likely opt out of the final two seasons of his three-year, $75 million contract and return to free agency. Will the Padres feel comfortable paying him like an ace after he posted a 3.15 ERA in three seasons with the Friars? If not, the Padres will be left empty-handed, as King will be ineligible for the qualifying offer after receiving it last offseason.
• Nick Pivetta's contract includes a $14 million club option for 2027. He made just eight starts in 2026, but you'd think he'd pick it up after finishing sixth in NL Cy Young voting in 2025.
• Also set to become free agents: Robbie Ray, Casey Mize and Walker Buehler. None of them were particularly good for the Padres, but they still have a lot of starts to make up for. Buehler, in particular, was an innings-eater for a team that desperately needed it.

So it will likely take a combination of free-agent signings and trades for the Padres to even have a full pitching staff in 2027, let alone improve their starting rotation.

Athletics

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Teams typically spend money the year before moving into a new park to build momentum. Given that the Athletics expect to move not only to a new stadium but also to a new city (Las Vegas) in 2027, one might expect them to be somewhat aggressive this winter.

First things first, they needed to get their new president of baseball operations up to speed. They fired David Forst in August, but only just landed their new top decision-maker on Monday, reportedly tabbed former Boston Red Sox assistant general manager Taylor Smith. Former Athletic Sam Fuld opted to remain president of business operations for the Phillies rather than take the position with the A's. Candidates probably had reservations about working with owner John Fisher, who isn't exactly known for spending big money.

Then again, Sacramento isn't a high-pressure market. Las Vegas is unlikely to be either. The A's have a pretty interesting core of young players in Nick Kurtz, Tyler Soderstrom, Jacob Wilson, Zack Gelof and Henry Bolte. Shea Langeliers could be a trade candidate this offseason with two years left until free agency, but the A's could also push to re-sign him after he was an All-Star in 2026. They'll also get back Brent Rooker in 2027 after he was limited to just 48 games this past year by a left knee injury that required season-ending surgery.

Obviously, the pitching has not kept pace with the offense. Part of that is that the A's have generally struggled to attract free agents when they play their home games at Sutter Health Park, a minor league stadium. It doesn't help that the minor league stadium has played like a bandbox. Still, the A's likely have only one year left in Sacramento, so they should be aggressive about improving their pitching, even if it means paying hazard pay to get free agents to overlook the fact that they'll be in a minor league stadium for one season.

If the free agent route doesn't work—and perhaps even if it does—they badly need to target pitching. If Langeliers is traded, it should be for a package centered on pitching. If someone likes the idea of Lawrence Butler as a change-of-scenery candidate, great; only move him if it's for pitching.