Saying goodbye to Jack Flaherty at the deadline was simply a given at the time. All but two of the Tigers' walk year players were gone by July 30, and Gio Urshela followed not long after. Shelby Miller is the last man standing, but he was untradeable at the deadline and has just managed to start regaining his footing as the last resort out of the Tigers' bullpen.
Flaherty's resurgence was a credit to the Tigers organization. After years of struggle, a trade, and a demotion to the bullpen, he signed with Detroit and put up one of the best ERAs in the American League while avoiding an IL stint despite back issues and a lengthy injury history. Although the return for him seemed far from ideal initially, and it left the Tigers with a lot of questions about how the pitching staff would manage with just two starters at the time, it wasn't surprising that a team as youth-centric as the Tigers would let him go.
It's turned out to be something of a win-win for everyone. Flaherty continues to dominate for the Dodgers, Trey Sweeney has been earning his keep in the major league lineup, and Thayron Liranzo continues to ascend on top prospect lists.
However, if talks about an extension rather than a trade had been broached, should the Tigers have kept Flaherty? Trevor Plouffe, a friend of Flaherty's and a Jomboy Media personality, said, " talked about it at the time. He wanted to be there. He would have accepted an extension from them if they'd just offered him."
Should the Tigers have kept Jack Flaherty if an extension discussion was on the table?
It is pretty miraculous that things have worked out quite as well for the Tigers as they have. No one expected Sweeney to perform as well as he did in Triple-A and get the early call, and even fewer expected the bullpen to be able to pull off what they've been able to do with the starter deficit, but the Tigers' pitching staff has put together the best team ERA since the deadline and starters are slowly making their way back.
The reality is that an extension was never going to happen. Even if things had gone differently with the rookies, trading him was the right thing to do. The Tigers were far from the postseason conversation at the time of the deadline, and they would've been loathe to spend a hefty amount on a pitcher when they could wait and get two Flaherty types in the offseason for a favorable price.
Without trading the veterans, there wouldn't have been room for the youth infusion, and without the youth infusion, the Tigers wouldn't be fighting for a playoff spot. Everything worked out exactly the way it was supposed to here, but it at least provides hope that Flaherty could return in the offseason on a long-term deal to help stabilize the rotation alongside Tarik Skubal.