The Toughest Contract Decision Facing the Detroit Tigers This Winter

The Tigers have a lot of work to do in the coming months, and with key free agents departing as well as some club options, they have a lot to decide in-house.

Tigers starting pitcher Jack Flaherty (9) throws a pitch against the Phillies. Credit: Lon Horwedel-Imagn | IMAGN IMAGES via Reuters Connect

If the Detroit Tigers do not want to face the same humiliation they did in 2026, there is a lot of work to be done to avoid the same fate in 2027, as there are many holes in the roster that need to be addressed.

First things first, the front office has to decide what to do with the players who have club options and those who are becoming free agents. Luckily, they have it really easy to select the contracts for both Kenley Jansen and Drew Anderson.

Neither Jansen nor Anderson should be in a closing role next year, as they accumulated 12 of the 29 blown saves by the relief staff, but both posted respectable ERAs and should rejoin the bullpen. That won't solve all their problems, but losing them would hurt the ballclub.

Jack Flaherty has been a key part of our pitching dominance since the start of June.

He owns a 1.90 ERA over that stretch, and takes the mound tonight after holding opponents scoreless in his last two starts.#DNMW pic.twitter.com/6ZV0nCtlMB

— Tigers PR (@DetroitTigersPR) July 10, 2026

The biggest questions are about their free agents, specifically Jack Flaherty, who performed worse than his career average. However, he really cleaned things up in his final seven starts, as he posted a 2.93 ERA.

The starting rotation is depleted after the team traded away both Tarik Skubal and Casey Mize at the trade deadline. Now, there are whispers that Skubal would like to return, but that still doesn't provide much depth in the rotation.

The Tigers’ Starting Rotation As It Currently Stands

Tigers starting pitcher Troy Melton (52) delivers a pitch against the Twins. Credit: Jesse Johnson-Imagn | IMAGN IMAGES via Reuters Connect

Some decisions are definitely going to need to be made regarding how the pitching staff is set up, but one thing that could be an option is keeping Anderson in the rotation, as he was thrown into that role after the deadline, and he posted a 3.19 ERA in his last seven appearances as a starter.

Then, there is Troy Melton, who was truly the saving grace this season, finishing with a 2.76 ERA in 20 starts. With Framber Valdez being so hot-and-cold in 2026 (4.03 ERA), that was clutch for the Tigers.

Jackson Jobe was also good in his limited time on the mound, but realistically, Detroit would benefit from another arm on the staff, as there can never be too many on the roster, as injuries always seem to pile up.

If the Tigers do decide to re-sign Skubal, they don't necessarily need Flaherty, but if the price is right to keep him in the clubhouse, then it would be a smart move by the front office to have him at the tail end of the rotation.