As a lifetime Yankees fan, there is no team I despise more than the Boston Red Sox.  I can’t stand the team, and I can’t stand people who played for them.  I never accepted Roger Clemens, Jacoby Ellsbury, Johnny Damon, or even Wade Boggs as a Yankee.  Sorry, but if you ever put on that uniform, I don’t want you on my team.  The Yankees clearly feel the same, as no one who played for the Red Sox is on the Yankees’ active roster.  Well, the same is not true for the Red Sox, as they kind of love former Yankees.  So, before we begin the first series against the Yankees’ hated rival, let’s see what former friends could potentially bite the Yankees in the rear end.

Aroldis Chapman

Let’s start with the one we all know the best, the former closer and fireballer, Aroldis Chapman.  Chapman wore out his welcome in the Bronx when he got his next tattoo.  He then went to Kansas City, Texas, and Pittsburgh, and none of us cared.  We did last year, though, when he turned up in Boston, and he finished 7th in the Cy Young voting as the most dominant reliever in the American League.  He has continued to be lights out this year, allowing 8 baserunners in 7.2 innings and just one run (even though his strikeouts are down).  Hopefully, the Yankees don’t see him in any close games.

Garrett Whitlock

 One of the worst roster decisions the Yankees ever made was leaving Garrett Whitlock unprotected in the Rule 5 draft.  He already has accumulated 8.4 WAR for the Red Sox as a star setup man in his 6th season.  He wasn’t good in 2023, but most would take his 141 career ERA+ any day of the week.  He is again solid this year, allowing 2 runs in 9 innings and recording 12 strikeouts.

Greg Weissert

 Yes, the Red Sox could beat the Yankees by using three former Yankees to finish the last three innings.  The Yankees sadly traded their former AAA closer, Greg Weissert, for a useless outfielder who lasted one season in the Bronx.  Weissert has accumulated 1.6 WAR in Boston in just his third season, but he has struggled this year, giving up 5 runs in 9.1 innings.

Caleb Durbin

The Yankees foolishly thought Devin Williams was their future closer, and in the process, they gave up a potential starting third baseman (who they really could have used last year) in Caleb Durbin.  Durbin finished third in the rookie of the year voting for the Brewers last year with a 256/334/387 slash line.  Alas, things haven’t worked out since he was shipped to Boston in the offseason.  To date, he is slashing a miserable .162/.260/.235.

Isiah Kiner-Falefa

 It would be harder to have a worse start than Durbin, who has an OPS+ of 44.  Well, IKF, in his debut season with an OPS+ of 34, has entered the chat.  I, like many Yankee fans, enjoyed watching IKF play for the Yankees and was intrigued by the possibility of his return.  Well, this was a good pass for the Yankees.  A .200/.259/.200 slash line simply hasn’t cut it.

Carlos Narváez

So, are you like me and confused as to why all the Yankee catchers are left-handed?  Well, it didn’t have to be that way.  Carlos Narváez had 15 at-bats for the Yankees in 2024 and could have been the catcher of the future.  The Yankees, however, shipped him to Boston for a hot prospect.  The jury is out on this trade, but in 2025, the return was all Boston as Narvaez finished 6th in the Rookie of the Year vote with a .241/.306/.419 slash line.  This year, however, he is off to a rocky start with just a .234/.265/.277 slash line.  

So overall, the Red Sox sure love former Yankees.  Three key relievers, their starting catcher, their starting third-baseman, and a utility infielder.  I even left out Sonny Gray, who is headed to the disabled list and wouldn’t have faced the Yankees anyway since he pitched yesterday (he is off to an average start with a 98 ERA+).  So, I hate to be a Negative Nancy, but with all these former Yankees, there is a good chance we can have an Oswaldo Peraza moment this week; hopefully, it doesn’t happen.