The Detroit Tigers seem like they're treading the upcoming offseason lightly when it comes to the free-agent market; however, there are a slew of talented players who could help fill holes within the organization.

This past offseason, Detroit showed it is willing to spend money when it's justified, as seen in its signing of Framber Valdez to a three-year contract worth $115 million. The Tigers find themselves in a unique position this offseason, with contracts expiring, which raises questions about the organization's future intentions.

2024-Like Offseason Scenario

This offseason holds a taste of 2024 to it. After the Tigers made the postseason by selling at the MLB Trade Deadline, most notably sending Jack Flaherty to the Los Angeles Dodgers for 1B/C Thayron Liranzo and SS Trey Sweeney.

Detroit fought back against 0.2% odds to make the playoffs and were postseason-bound for the first time since 2014. Flaherty and the Dodgers would go on to win the World Series, sending Flaherty back to free agency after his one-year contract expired.

He would then sign a two-year deal with Detroit that offseason, so the Tigers reunited with Flaherty and gained two prospects.

This season, the Tigers' poor performance forced the front office's hand to trade back-to-back American League Cy Young Tarik Skubal to the Dodgers in exchange for three prospects, Zyhir Hope, River Ryan, and Brady Smith.

So the Tigers traded their best pitcher from 2024's first half (Flaherty) to the Dodgers and they won the World Series. The franchise did the same this season (trading Skubal), yet Los Angeles wasn't World Series-bound.

Now, Skubal hits free agency. See the scenario?

Why Re-Signing Skubal Will Be Harder Than When Detroit Re-Signed Flaherty

For starters, the Tigers re-signed Flaherty to a two-year, $35 million contract after winning the World Series with the Dodgers. When Flaherty originally signed with Detroit, it was a one-year, $14 million deal and he was the second-highest-paid player on the roster that season (2024: Javier Baez = $23.3 million).

In 2025, Flaherty made $17.5 million and was the second-highest-paid player on the roster, again trailing Baez. That financial flexibility allowed Detroit to reacquire Flaherty, especially at that price.

Skubal made history, earning $32 million via arbitration in 2026, meaning he was already more expensive than Flaherty was before he hit free agency for the first time. Now that Skubal is back on the free-agent market, the Tigers face a scenario where they could lose nothing from a trade with the Dodgers if they re-signed their ace.

In 2026, Skubal was the Tigers' second-highest-paid player behind Valdez, but at much higher values compared to when Flaherty was re-signed.

There is a world where the Tigers do this, but it's likely not a world we're living in. Seeing that Skubal pitched well in Los Angeles, he'll likely look for a $325-$400 million contract in free agency, which would make him the highest-paid pitcher in baseball history, surpassing Yoshinobu Yamamoto's $325 million guaranteed.

Which would mean they would need to give him more than what Valdez is making with the franchise, which is only increasing ahead of year two. Ultimately, if Skubal was meant to be a Tiger for life, the front office would've extended him rather than trading him.

So, sure, the Tigers face a similar offseason scenario to what they did after 2024 in 2026, but the cost has significantly increased. The New York Mets have been reported to be a team willing to go into a bidding war over the two-time Cy Young Award winner this offseason, likely removing Detroit from the conversation.

Not to mention, with an MLB lockout looming as the Major League Baseball Collective Bargaining Agreement ends Dec. 1, 2026, franchises might not hesitate to open the checkbook to sign Skubal as quickly as possible (post-World Series), whereas when Flaherty re-signed with the Tigers, it was in Feb. 2025, much after the end of the World Series and without a lockout looming.