After starting his career with the St Louis Cardinals, Flaherty was traded at the 2023 trade deadline. He was moved to the Baltimore Orioles, as they closed out the first division title in the Baby Birds era. That experiment was a disaster, as he made seven starts in the regular season and posted a 6.75 ERA. That poor second half landed him a one-year deal with the Tigers. A longer-term deal is coming after his strong 2024.

There are plenty of teams looking for a pitcher this offseason. Flaherty will be a solid option for each of these teams this offseason.

Top option: Return to Detroit

The Tigers were on the cusp of the playoffs when they traded Jack Flaherty at the deadline. They then went on a run the Motor City will remember forever. Their 30-13 run to close out the regular season and win over the Astros in the Wild Card Series came with one true starter. Tarik Skubal will likely win the Cy Young Award but he cannot do it alone in 2025.

This is the offseason that Tigers fans have been waiting for. They have a solid core, money to spend, and big-time targets who fit their needs. There are not many needs on the team, as everyone carried their weight on the way to the ALDS. Starting pitching is one of them and both sides know that Flaherty fits well in Michigan.

In 18 starts with the Tigers, Flaherty posted a remarkable 2.95 ERA. As the second man behind Skubal, he was tremendous and helped lay the foundation for the excellent run. Assuming the relationship is solid on both sides, this deal would benefit both sides for a long time.

#2: The Yankees get a do-over

When the Tigers were shopping Flaherty, they had a deal to send him to the Yankees. New York pulled the plug at the last second because of a concern in the medicals. With more time to work out a deal and proof of health in their stadium in the World Series, that concern should go away. The Yankees need another strong starter and should target Flaherty to be that guy.

While Flaherty is a great pitcher, he will not cost as much as some of the other aces on the market. That is ideal for the Yankees, who are trying to save every dollar to re-sign Juan Soto. They can bring Flaherty in and slide him in behind Carlos Rodon and create a dominant playoff rotation.

There are plenty of trade options that the Yankees should be interested in. That includes Garrett Crochet, who will cost almost nothing against the luxury tax. Flaherty could be their fallback if the White Sox decided to hold onto Crochet and other trade options like Sonny Gray fall through.

#3: Jack Flaherty heads to Queens

Across New York City, the Mets are poised to spend in free agency. Their makeshift rotation shined on their run to the NLCS but Luis Severino, Sean Manaea, and Jose Quintana are all free agents. Replacing one of them with a bona fide ace would spring the Amazins into contention for the World Series.

Flaherty would be a perfect fit for the Mets after their great season. They saw in Game 1 of the Championship Series how dominant he can be, shutting down New York to give the Dodgers a lead. It would not be surprising if the Mets brought two of their pitchers from last year back but they will need an Opening Day guy to solidify their group.

If Steve Cohen and David Stearns pick Flaherty as their top pitching target, they are unlikely to get outbid. Cohen is the richest owner in sports and they just got dead money from 2022 off their books. Juan Soto is the biggest fish in the pond this free agency period and the Mets are in the race. Flaherty should be less expensive than Burnes, Fried, and Snell, so he might be good for New York if they do get Soto.

#4: A new ace in Beantown

The Red Sox made headlines this week with their Juan Soto meeting. Putting their hat in that ring shows their commitment to opening up their checkbook. They have not signed a big-money free agent in a long time but need one to power out of their rebuild. Flaherty would be a great option to lead the rotation with Lucas Giolito.