Tarik Skubal is the headliner of the MLB free-agent market. The two-time American League Cy Young Award winner is coming off another outstanding season and is positioned to land one of the largest contracts ever given to a starting pitcher. The Dodgers, Mets, Cubs and Yankees are among the leading contenders, although the Detroit Tigers should not be completely ruled out.

The race will ultimately depend on each team's needs, financial flexibility and, most importantly, its willingness to commit to a deal that could exceed $350 million. With MLB's collective bargaining agreement approaching its expiration date, the coming weeks could prove decisive in determining the star left-hander's next destination.

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Los Angeles Dodgers

The Dodgers have plenty of reasons to emerge as one of the leading contenders for Tarik Skubal. Los Angeles is already familiar with the left-hander after acquiring him from Detroit ahead of the 2026 trade deadline in a deal that sent three prospects to the Tigers.

Skubal made a strong impression during his time in Los Angeles, posting a 2.61 ERA across 10 starts. His performance showed that he could deliver at an elite level even after switching organizations in the middle of a season.

From a baseball standpoint, adding Skubal would help the Dodgers maintain one of the league's top rotations while reducing their reliance on other starting pitchers. Financially, few franchises can match Los Angeles when an opportunity to acquire a player of this caliber presents itself.

The biggest question is how the Dodgers choose to allocate their resources. They also have bullpen needs to address, with several key relievers potentially entering free agency. Still, it is difficult to imagine a franchise accustomed to pursuing elite talent passing on a pitcher like Skubal simply because of budget considerations.

The familiarity between the two sides could also work in Los Angeles' favor. The Dodgers have already seen firsthand what Skubal brings to the mound. Now, they have an opportunity to turn that successful short-term partnership into a long-term commitment.

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New York Mets

The Mets have one of the biggest financial advantages in this race: owner Steve Cohen. New York's billionaire owner has repeatedly shown a willingness to spend aggressively when he believes an opportunity could transform his roster.

The organization needs to upgrade its rotation after missing the playoffs for the second consecutive season. Signing Skubal would give the Mets an established ace capable of leading a staff that features several talented young arms and raising the team's competitive ceiling.

Jon Heyman of the New York Post reported on the Mets' interest in the left-hander. The bigger question, however, is how far president of baseball operations David Stearns and the front office are willing to go financially.

Cohen's pursuit of Juan Soto demonstrated that he has no reservations about participating in historically expensive negotiations. Still, Stearns has generally taken a more cautious approach to long-term commitments involving starting pitchers.

Skubal could be an exception. His age, track record and status as a two-time Cy Young winner make a massive investment easier to justify. If the Mets want to reestablish themselves as contenders in the National League, this could be one of the most consequential moves of their current era.

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Chicago Cubs

The Cubs are among the most intriguing potential destinations, largely because their need for starting pitching is difficult to ignore.

President of baseball operations Jed Hoyer has identified the rotation as one of the organization's top priorities this offseason. Several important pitchers could also leave Chicago through free agency, making the need for reinforcements even more pressing.

Jeff Passan of ESPN reported that the Cubs have considerable interest in Skubal, although there are questions about whether the organization is willing to meet the financial demands his market is expected to generate.

That is the biggest obstacle. Chicago has the financial flexibility to make a significant investment, but its history does not suggest a franchise accustomed to handing out contracts worth more than $300 million.

The Cubs' largest contract remains the $184 million deal they gave Jason Heyward in 2016. Going substantially beyond that figure would represent a major shift in the franchise's spending philosophy.

Even so, the Cubs have an opportunity to make a statement. Landing Skubal would address an obvious weakness while sending a clear message about the organization's ambitions to return to the top of the National League.

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New York Yankees

The Yankees do not necessarily need another starting pitcher, but that does not mean they should be excluded from the conversation.

New York already has an impressive rotation featuring Gerrit Cole, Carlos Rodón and Max Fried. However, ESPN's Kiley McDaniel reported that the Yankees would at least consider making an offer for Skubal.

The potential strategy could make sense if the Yankees subsequently use some of their pitching depth to address other roster needs.

Ryan Weathers, Will Warren and Clarke Schmidt could all represent potential trade pieces. In that scenario, New York could acquire the best available pitcher on the market before reshaping other areas of its roster through trades.

The Yankees also have a track record of making massive commitments to elite pitchers. The franchise has shown a willingness to offer contracts spanning six, seven or even nine seasons when the right opportunity arises.

The challenge would be justifying such a substantial investment when other needs remain, particularly in the infield and behind the plate. Still, if the front office believes Skubal could significantly improve its chances of winning a World Series, it would be difficult to dismiss the opportunity outright.

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Detroit Tigers

Although the Tigers may have a harder time matching the financial resources of baseball's biggest-market teams, they deserve a place in this conversation for a different reason: Skubal already knows the organization and has expressed interest in returning.

Detroit made the decision to trade him ahead of the 2026 deadline, acquiring three prospects in exchange for one of the best pitchers in Major League Baseball. That transaction, however, does not prevent the two sides from reuniting through free agency.

General manager Scott Harris has generally shown patience when pursuing starting pitchers. Detroit signed Framber Valdez to a three-year, $115 million contract after he remained available for much of the previous offseason.

The Tigers had also pursued Jack Flaherty under similar circumstances during an earlier offseason.

Skubal, however, belongs in a different category. This is not a pitcher looking to rebuild his market value. He enters free agency as the top starting pitcher available and arguably the most coveted player on the entire market.

Detroit would therefore need to make an extraordinary financial commitment to compete with the other contenders. Its best-case scenario might involve the market falling short of initial projections or Skubal placing additional value on returning to an organization where he is already familiar with the environment.

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A Historic Contract Before a Potential Lockout

Money will ultimately play a decisive role in determining Skubal's future. ESPN's Kiley McDaniel projected an eight-year, $352 million contract, which would carry an average annual value of $44 million.

That projection is hardly unreasonable given Skubal's recent performance. According to MLB.com, since returning from flexor tendon surgery in July 2023, he has gone 50-20 with a 2.47 ERA and accumulated 21.2 fWAR across 103 starts.

There is another factor that could accelerate negotiations: MLB's collective bargaining agreement expires on December 1, 2026, at 11:59 p.m. ET. With a potential owner-imposed lockout looming the following day, players and teams could be motivated to resolve major negotiations before the deadline.

In fact, a survey of 27 industry sources conducted by McDaniel found that 21 expect Skubal to sign before the current agreement expires.

The race remains wide open, but the Dodgers and Mets appear to have significant advantages because of their financial resources and competitive needs. Chicago could emerge as a surprise contender if it decides to break from its historical spending patterns, while the Yankees have the resources to enter the bidding even if starting pitching is not their top priority.

Detroit, meanwhile, still has its existing connection with its former ace, although bringing him back would require an extraordinary financial offer.

One thing seems certain: Skubal is in position to headline one of the most consequential free-agent negotiations of the 2026-27 MLB offseason.