Insider Reveals Yankees Backed Out of Blockbuster Deal for Star Pitcher

The Yankees lost a bidding war with the Dodgers for an ace... or did they?

Jul 19, 2024; Toronto, Ontario, CAN; Detroit Tigers starting pitcher Jack Flaherty (9) pitches to the Toronto Blue Jays during the third inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-USA TODAY Sports / John E. Sokolowski-USA TODAY Sports

Although the New York Yankees had a fairly successful trade deadline overall, they almost landed one of the most coveted targets available.

According to MLB insider Ken Rosenthal, the Bronx Bombers shockingly backed out of a preliminary trade agreement with the Detroit Tigers that would have sent stud right-hander Jack Flaherty to the Bronx; the Tigers subsequently pivoted and sent the 28-year-old Flaherty to the Los Angeles Dodgers.

The Yankees decided to back out of the deal due to concerns of Flaherty's medical records; he had missed a start in the first week of July with a lower back issue and even recieved three injections over a three-week span. This hasn't seemed to affect his play on the field, as he logged a 1.53 ERA in his next three starts, but it was enough for New York to think twice about trading for him.

“I can’t comment on medical stuff with trades,” Tigers president of baseball operations Scott Harris said to Detroit reporters. “You would have to ask the other teams. Jack is healthy. If we didn’t trade him, he was going to start for us on Thursday.”

Sources: Yankees backed out of trade for Jack Flaherty because of medical concerns. Story: https://t.co/Eq8dBVhXXN

— Ken Rosenthal (@Ken_Rosenthal) July 31, 2024

One possible reason why the Yankees weren't willing to take any chances on Flaherty is their trade for Frankie Montas two years earlier. At the time of that trade, Montas was dealing with right shoulder tightness and would only throw 39.2 innings for them for the rest of the 2022 season. These shoulder issues became even worse in 2023 and led to surgery; he wouldn't be activated that season until September 30, which was the Yankees' penultimate game of the year. Ultimately, Montas only pitched 41 innings across one-and-a-half seasons in pinstripes. (Montas would also be traded during this year's deadline, going from the Cincinnati Reds to the Milwaukee Brewers.)

Rosenthal also reported that while the Yankees and Dodgers were the only teams to review Flaherty's medicals (due to these reviews typically being done after agreeing to a deal), other teams became aware of New York's concerns with Flaherty after they backed out. But while these back issues raised a red flag for the Yankees, they didn't for the Dodgers (who already are dealing with numerous injuries to their starting pitchers), who subsequently landed the Tigers' standout with a package that included ex-Yankees prospect Trey Sweeney.

It is also worth mentioning that, according to a report on Monday from fellow insider Bob Nightengale, the Yankees intended to trade starting pitcher Nestor Cortes Jr. if they acquired Flaherty. With Cortes leading the Bronx Bombers with 124.1 innings pitched this season, trading him away would be an extremely risky move in the event that Flaherty got injured; New York also dealt with this scenario at the 2022 deadline, when the acquisition of the unknowingly injured Montas led them to trade fellow starter Jordan Montgomery to the St. Louis Cardinals in a much-maligned move.

In the end, the Yankees were still able to bring in impact players before the 6 PM deadline on Tuesday; both Jazz Chisholm Jr. and Mark Leiter Jr. were integral to their victory over the Philadelphia Phillies that night, while another strikeout reliever in Enyel De Los Santos was added in a last-second trade to bolster the bullpen. However, they could have gotten the best pitcher on the market, and this shocking decision could loom large if they end up falling short of a World Series title this year.