MLB free agency: Analysis of Tigers’ options with Tarik Skubal
Will baseball’s best pitcher change teams this offseason? Industry experts give their opinion.
After three seasons with a superstar who had become the face of the franchise and topped the winter free agent list, there is no Aaron Judge, Shohei Ohtani or Juan Soto in the 2025-26 free agent class. But there’s still one player whose potential availability could shake up the offseason: Tarik Skubal.
Why might the Detroit Tigers trade their ace just after winning their second consecutive American League Cy Young Award and the team making the postseason for the second consecutive year?
Simply put, keeping Skubal in Detroit will become very expensive very soon. The 28-year-old left-handed pitcher will enter the final year of his contract in 2026 before becoming a free agent after the season. If he hits the market next winter, Skubal has a chance to surpass Los Angeles Dodgers ace Yoshinobu Yamamoto’s $325 million record and could even become the first baseball pitcher to earn $400 million.
With Tigers president of baseball operations Scott Harris facing a decision that will define the future of the franchise – and impact the entire MLB – we spoke with 11 industry experts about what Detroit should do this offseason, breaking the information down into three main options.
1. Trade Skubal this winter
This was the least popular option among our panel, and an executive from a rival team explained why.
“This is all done to start the season with a potentially contending team that has an ace up its sleeve. You can’t waste that before the season starts. How long will it take to get back here?”
Some panelists were hesitant about how much a team would have to pay for Detroit to consider a trade, believing that an offer that included a young starting pitcher with top-line potential would be enough to start internal talks; However, no one could be convinced of the logic of an agreement unless something completely illogical was offered. And those types of deals are becoming less common in modern baseball.
If the Tigers were to trade Skubal for anything other than exorbitant compensation, it would likely mean their competitive edge would shrink, and it would be difficult to consider Detroit a contender without Skubal next season. Getting rid of a player of his caliber would label the Tigers a small-market team, at least in mentality, and call into question whether they would find themselves in this situation again as other stars approach free agency. It’s much easier to bet some, but not all, of their cards for next season and see what they can do with Skubal at the helm. Who knows when the next opportunity will come?
When I asked these sources what the Tigers should do, they seemed undecided about Detroit’s outlook, but were inclined to believe they would keep Skubal for next season. That said, Harris likes to know what the market can pay, so the insistence that Skubal be available with the right offer, or at least that Detroit be willing to listen before ruling him out, will likely continue.
2. Keep Skubal, but transfer him before the market closes if the season does not develop as planned.
In case things get complicated during the first half of the 2026 season, all members of our panel agreed that this was the right decision. Defining what it means to “get complicated” with the expansion of the playoffs is complex, but the fight for a wild card spot near the market close was where the uncertainty began for our panelists.
“Under no circumstances can Skubal be retained until the market closes and miss the playoffs. It would be a catastrophe,” said one agent.
The haul would still be formidable for a temporary transfer: a rough calculation indicates that you could get two prospects ranked later in the top 100 or a young elite player, broadly speaking. Additionally, the offers would have to meet the requirement that Detroit receive a compensatory pick right after the first round to even be considered, since that’s what the Tigers would get if Skubal left as a free agent (under the current free agency system).
Another rival executive has an informed theory about Harris’ approach: “He’s eyeing 2027 and 2028 as his best years to compete for the title.” If things go well in 2026, that period would be extended to include it as well. Top prospects Kevin McGonigle and Max Clark, the sport’s No. 2 and No. 6, could be key players as early as the second half of 2026, so targeting a real breakout in 2027 is logical.
There are mixed opinions on whether Skubal would bring in more revenue this winter or at the trade deadline, as it’s difficult to predict how desperate a contending team might be at that point, compared to what they would offer to get a full season out of Skubal plus a first-round pick when he leaves. It is safe to assume that the consideration would probably be lower at the deadline.
3. Keep Skubal at all costs, try to extend his contract and get the draft pick if he eventually leaves.
This would be a bold move in the current era, where many teams are focused on maximizing the value of their assets. If Skubal were to leave as a free agent, the compensation would likely be a top-30 draft pick the following summer, and nothing more. That type of selection has an approximate value of between 8 and 10 million dollars, depending on the source.
There is more value to Detroit before that, but it’s hard to quantify. The Tigers would have another shot at the title with the reigning two-time American League Cy Young winner and more time to convince him to stay in Detroit. Perhaps that combination could work wonders and both sides would reach an agreement before he becomes a free agent. Skubal has said he wants to stay in Detroit, so that can’t be ruled out. Another rival executive believes Harris is focused on how to achieve this. “(Harris) will never believe he can’t sign Skubal.”
That said, the fact that Skubal is represented by Scott Boras makes it unlikely that he will sign a contract without at least testing the market, as Boras often advises his clients to opt for free agency.
However, there is one more variable unique to when Skubal becomes a free agent: the foreseeable labor dispute next winter, given that the current collective bargaining agreement expires on December 1, 2026. Boras is unlikely to want Skubal to be available during a strike that could force him to sign just before spring training, after some teams have exhausted their budget and with the economic model of the game potentially changing in a way that hurts his market value. One source said the CBA complication raises the odds of Skubal signing an extension before free agency from 0% to 10%.
The last time a strike affected free agency, a flurry of deals occurred in late November before the Dec. 1 lockout. A similar, faster free agency process culminating in Skubal’s signing around Thanksgiving would give Detroit a slight advantage, given the familiarity with the process and the exclusive negotiating period leading up to free agency, compared to a protracted bidding war all winter.
The contracts to beat are Yamamoto’s $325 million guarantee, the highest ever given to a pitcher, and Max Fried’s $218 million guarantee, the highest ever for a left-handed pitcher. Both contracts were managed by agencies other than Boras Corp., and establishing precedents is a fundamental part of the marketing strategy of the main agencies to attract potential clients with million-dollar contracts.
Also worth noting is that Skubal underwent Tommy John surgery in college and flexor tendon surgery in 2022, factors that should be taken into account when projecting a long-term deal in free agency.
Are Harris and the Tigers likely to win a straight bid with an unprecedented guarantee? No, but if they can offer a shorter contract with a record average annual salary and buyout clauses, they would at least have a chance, albeit a slim one, of retaining their ace.
The real problem for Detroit is its payroll. They finished last season with a payroll of $155 million subject to the competitive balance tax (CBT), more than $90 million below the first CBT threshold. If Skubal is going to make an average annual salary of $30 million, or even just over $40 million, can the Tigers really justify spending a quarter of their payroll on a single player? Would Harris do it, or would hiring Skubal be part of a larger strategy to achieve a payroll that justifies his inclusion, now that the Tigers see their best competitive moment beginning? If McGonigle and Clark perform at their peak late in 2026 and prove to be future stars, that won’t increase payroll, but it could make the Tigers more competitive going forward, which could also strengthen their long-term bid to retain Skubal.
This logic – if things go well in 2026, the Tigers will compete and manage to retain Skubal for the entire season – explains why another executive mulled Detroit’s options if it traded Skubal before the market closed. “You could still trade (Skubal) and then re-sign him long-term, but I can’t imagine what the circumstances would be like for that to happen.”
There is also the analysis of the signals for this winter. Some sources mention that Detroit is looking to strengthen its pitching staff at the start of free agency. Is it to cover a possible departure of Skubal? A deal now or before the deadline? Or simply to create depth for the title fight, as all contending teams need? Or to generate greater flexibility and options for the entire 2026 season? Everyone interprets what they want to see in this winter team-building enigma.
