Philadelphia Before Tuesday’s trade deadline, Brian Cashman made his purchases without missing any departments. The general manager of the New York Yankees searched the market for relievers who could pitch both left- and right-handed. He went after infielders. His eyes searched the outfielder’s aisle. He looked for introductory pitching. He was captivated by one player in that specific location to the very end.

By far the greatest starting pitcher dealt on Tuesday, Jack Flaherty, was available to two teams, including the Yankees. He was acquired from the Detroit Tigers. Just before 6 p.m. ET, the Tigers moved him to the Los Angeles Dodgers in exchange for two minor leaguers; as a result, the Yankees acquired utilityman Jazz Chisholm Jr. and relievers Mark Leiter Jr. and Enyel De Los Santos as deadline hauls.

During a conference call with reporters on Wednesday, Cashman said that the Yankees’ willingness to pay for Flaherty to improve a rotation that has struggled lately was impacted by the player’s recent back ailment. However, he made it clear that he “was in it all the way to the end” prior to the Tigers dealing the native Los Angeles native Flaherty to his home team.

“At the end of the day, I would’ve brought Jack Flaherty in if I could’ve matched up and I had difficulty matching up,” Cashman stated. “And that was the reason I don’t have him.”

This is the second season in a row that Flaherty, 28, was dealt at the deadline. But his value took a significant turn for the worst from last year to this one.

Flaherty was a struggling pitcher last summer who was attempting to regain his former level of dominance. Due to the low demand for his skills, the St. Louis Cardinals dealt the rental to the Baltimore Orioles in exchange for three mediocre prospects. By the end of the regular season, Flaherty had been demoted to the bullpen due to his extreme struggles in Baltimore. In 29 appearances (27 starts) between the two clubs, he concluded with a 4.99 ERA.

In December, the Tigers signed him to a $14 million, one-year pillow contract, searching for value. The purchase turned into a great deal. For Detroit, Flaherty recorded a 2.95 ERA in 106 ⅔ innings pitched. He made eighteen starts and completed at least five innings in each. He has 19 walks compared to 133 strikeouts.

However, a lower back problem that required two injections over the course of three weeks caused him to miss a start at the beginning of July. Since coming back on July 11, Flaherty doesn’t seem to be affected by the issue. In three appearances, he limited opponents to three runs over 17 ⅔ innings.

After Garrett Crochet declared he wouldn’t pitch in the postseason without a contract extension, Flaherty was the obvious top starting pitcher available for a deal.

Since June 1, Flaherty’s 5.17 ERA—the fourth-highest in the majors—has been plaguing the Yankees, and they wanted him to improve the rotation. With so many uncertainties around their rotation, the Dodgers, the storied team on the opposite coast with yearly championship-or-bust expectations, wanted him to have another elite option for October.

In the end, Flaherty was signed by Los Angeles to start at the top of their rotation. Using what they have, the Yankees will try to win the pennant in the end by hoping that Clarke Schmidt can recover from his injury without incident and Gerrit Cole can return to Cy Young form.

“In the end, we failed because we couldn’t match up on value,” Cashman stated. “That’s all.”

Recent data demonstrates how badly Tigers executive Scott Harris mishandled the trade for Jack Flaherty.

Allow me to return the favor: It is April 20, 2023, the day of the MLB trade deadline. Scott Harris, the president of baseball operations for the Detroit Tigers, is in communication with the Los Angeles Dodgers to finalize the Eduardo Rodriguez deal. Naturally, Rodriguez’s no-trade clause and his desire to play for Los Angeles present the only issues.

Even though Harris wasn’t solely to blame for this error, critics and supporters alike attacked him for it. Rodriguez would sign a free agent contract with the Arizona Diamondbacks, leaving the Tigers.

A year later, Harris found himself in a same situation. Jack Flaherty was the best rental available, and a failed deal for him with the New York Yankees was supposedly caused by medical concerns. Two minutes before the deadline, Harris had little alternative but to make an unimpressive trade with the Dodgers because he had positioned himself too long, looking for the best return after fellow pitchers like Yusei Kikuchi drove up the pitching market.

Kids, this is why you don’t put off doing your homework till the last minute.

Scott Harris missed the Tigers trade deadline once more.

Worse, according to Tigers beat writer Evan Petzold of the Detroit Free-Press, Harris could have accepted the same offer the Blue Jays received for Kikuchi, but they shifted because Harris was being demanding in their talks with the Astros at the time. It was also revealed by Petzold that, just two hours prior to the trade deadline, Harris would not reduce his asking price for Flaherty.

Let me be clear: Harris appears to be a capable president of baseball operations. He’s just started his second year of work and is young. Tigers supporters don’t need to panic. The last two deadlines have also been tough for him; he believed Rodriguez would sanction a deal with the Dodgers, and now, given how well Flaherty has been pitching this month, the Tigers were caught off guard by medical concerns.

But Harris found out the hard way on Tuesday night that a front office that doesn’t learn from its mistakes is bound to repeat them. The most egregious error in his judgment came when he held off on lowering his asking price for Flaherty in spite of his injury concerns, giving in at the eleventh hour. The Tigers are brutally honest when they say they have a poker face. All the contenders were aware that they were going to trade Flaherty, particularly after Detroit pulled him from what was supposed to be his final start.

Trey Sweeney and Thayron Liranzo might develop into good, if not great, players, but Harris’s insanity must have a reason. The whole of baseball, including Andrew Friedman, knows his number.