Yankees Weigh Risky Trade That Could Become Another Regret
The New York Yankees have a history of trades that turned sour—sending away young talent who later thrived elsewhere. Names like Willie McGee, Doug Drabek, and Jay Buhner are reminders of what can happen when a team bets on the present and loses the future.
Now, Rafael Flores could be the next name added to that list.
The Yankees are fully focused on winning in 2025 and are expected to be active ahead of the trade deadline, especially in bolstering their bullpen. But with the market favoring sellers this year, General Manager Brian Cashman may need to pay a steep price to land top talent.
One proposed trade by Newsweek’s Jon Vankin suggests New York could acquire All-Star closer David Bednar from the Pittsburgh Pirates in exchange for Flores, a 24-year-old catcher currently playing at Double-A Somerset.
On paper, the move makes sense. The Yankees have bullpen concerns after injuries and underperformance from recent additions like Luke Weaver and Devin Williams. Bednar has a strong résumé, including an NL-best 39 saves in 2023. Although he struggled with control earlier this season and was temporarily demoted to Triple-A, he has since returned to form—recording 32 strikeouts and only three walks over 21.2 innings, going 8-for-8 in save chances.
MLB.com recently named Bednar one of the top relievers available ahead of the deadline, noting that his improved performance and one remaining year of team control could raise his trade value.
Still, trading Flores may be a high price to pay.
An undrafted player from Southern California, Flores has developed into one of the Yankees’ top prospects. He won the 2024 Kevin Lawn Award as the organization’s top minor league position player and was also named Minor League Player of the Year by Baseball America. So far in 2025, he’s slashing .290/.345/.498 with 11 home runs and 39 RBIs—among the best in the Eastern League.
Scouts praise Flores for his raw power and plate discipline, though they note he still needs work with pitch recognition. Defensively, he’s considered average behind the plate but shows promise due to his size, footwork, and versatility.
With the Pirates likely seeking multiple prospects for Bednar, the Yankees must weigh the benefits of adding a proven closer against the risk of giving up a rising talent who could flourish elsewhere.
If the Yankees fall short of a championship, such a trade could join a long list of regrettable decisions.
About the Author
