Unsurprisingly, Jack Flaherty was one of the hottest commodities on the trade market this season as one of very few starting pitchers available for a handful of buying teams. Ultimately, he was one of only a couple of top starters to be moved at all, as Garrett Crochet, Tarik Skubal, and Tyler Anderson all stayed put. The Dodgers eventually won out, getting away with highway robbery as they sent just two prospects to Detroit for him, but the Orioles, Phillies, and Yankees were all reported as being in on the chase.
Quickly after Flaherty became a Dodger, the Yankees' side of the story leaked, as Ken Rosenthal of The Athletic reported that they backed out because of medical concerns (subscription required). This was a pretty transparent plant right from the start — there's no way the Yankees didn't already know about Flaherty's back issues and the injections he received to treat the problem. It was quick PR for a team with a perpetually angry mob for a fanbase.
The day after the deadline, Yankees GM Brian Cashman appeared on SNY and was asked about the "medical concerns" excuse for not getting Flaherty. Instead of addressing the question directly, Cashman said, "I would've brought Jack Flaherty in if I could've matched up, and I had difficulty matching up."
The interviewer pressed, asking, "You're saying there was not a medical concern on the team's part?"
Cashman said, "I'm saying what I answered just now. I had trouble matching up on the values."
Brian Cashman refused to take accountability for not making Yankees-Tigers trade for Jack Flaherty happen
Okay, Brian. Maybe you should've just followed the line of argument that your team already had laid right out in front of you instead of both seemingly blaming the Tigers for asking for too much and exposing said argument as a flimsy half-truth.
It could be that the Tigers were getting close to the wire and felt that they had to accept a smaller deal from the Dodgers for Flaherty if they wanted to move him at all. There certainly have been rumblings that Scott Harris overplayed his hand and missed out on a potentially larger deal, like the one the Blue Jays received for Yusei Kikuchi from the Astros. However, given how small the Dodgers' end of the deal was, it seems that any other team with a pretty good farm system could've outdone it easily.
Either just double down on the medical concerns or say you were too stingy to give up a handful of prospects and go.