Having a critical challenge in the Yankees’ Bryan Reynolds trade

According to MLB insider Jon Morosi, the Yankees have been in contact with the Pirates about Reynolds in recent weeks, but there is an “obstacle.”

What is the stumbling block to the Yankees reaching an agreement?

Bryan Reynolds

Following the departure of free agent Andrew Benintendi to the Chicago White Sox. The Yankees’ best option is undoubtedly outfielder Bryan Reynolds of the Pittsburgh Pirates, but the Pirates’ asking price is reportedly exorbitant. Despite this, the New York Yankees have inquired about Reynolds.

The Pirates are reportedly looking for starting pitching in exchange for Reynolds, and the Yankees don’t have many top-tier starting pitching prospects.

According to MLB.com, the top five players in the Yankees farm system are all position players. In exact order, their top five players are shortstop Anthony Volpe, outfielder Jasson Dominguez, shortstop Oswald Peraza, catcher Austin Wells, and outfielder Everson Pereira.

The Yankees’ top starting pitching prospects are Will Warren (No. 8), Clayton Beeter (No. 9), and Luis Gil (No. 10), all of whom are ranked near the bottom of the top 10. (No. 10).

This season, the Yankees did trade some starters from their farm system at the trade deadline in order to bolster their roster for a postseason run.

In exchange for Frankie Montas, the Yankees sent No. 5 prospect Ken Waldichuk and No. 7 prospect Luis Medina to the Oakland Athletics. Waldichuk is currently Oakland’s second-best prospect, while Medina ranks 14th.

The Yankees then traded relief pitcher Scott Effross to the Chicago Cubs for then-No. 7 prospect Hayden Wesneski. Wesneski appeared in six games (four starts) for the Cubs last season, recording a 2.18 ERA, 0.94 WHIP, and a 3-2 record.

According to Morosi’s report, the Yankees’ arsenal may be insufficient to facilitate a trade. Given how much they want in return, convincing the Pirates to part ways with Reynolds was always going to be difficult. Reynolds, after all, is under team control until the 2025 season.