Six current Boston Red Sox were, at one point in their career, part of the New York Yankees organization. In the not-too-distant past, it would have been criminal for this many players (23% of the roster) to have been from New York, especially when three of them came directly from the Bronx without a stop in between.
Recent times have seen the two teams make a couple of trades, although nothing groundbreaking, showing the softening borders between the two. That doesn't mean that Boston using their former players against them won't make a potential series victory over them that much sweeter for Red Sox Nation.
Aroldis Chapman, Garrett Whitlock, Greg Weissert, Justin Wilson, Carlos Narváez, and Rob Refsnyder are all former Yankees. That's not new news, every one of those players gets highlighted when the two teams face off, but it's never quite this many players as impactful to the Sox's success.
In the 2021 Wild Card game, only two were former Yanks: Nathan Eovaldi and Adam Ottavino. When the two squads faced off in the 2018 ALDS, it was three: Eovaldi, Eduardo Nunez, and Steve Pearce (who played 12 games with the Bombers in 2012). In 2018, those three players accounted for 1.0 bWAR; in 2021, it was 5.1, and this year it's 11.3.
Former Yankees have already beat up on their old team as Red Sox this season
Insane season from 44 🔥 pic.twitter.com/fwxxmDJNlr
— Section 10 Podcast (@Section10Pod) September 30, 2025
The Red Sox have taken players that the Yankees left for scraps and turned them into gems, and gems that are going to play pivotal parts in any success the Red Sox have this postseason. Just look at the projected starters for the Yankees in games one and two, Max Fried and Carlos Rodón, who are both lefties. Refsynder hit .333 against them with two walks this season.
Chapman, once the Bombers' great closer, had a resurgent season and, when facing them, allowed just three hits in six innings against them and got five saves. Whitlock, whom the Red Sox took from them in the Rule 5 Draft, struck out nine and didn't allow a run in 7.1 innings. Narváez had a .978 OPS against them in 11 games, including an OPS over 1.000 in six games in Yankee Stadium.
The Red Sox's recent CBOs have done an excellent job at identifying talent. When that becomes stealing talent from the Sox's biggest rival, and then using them to potentially beat them in a playoff series, it's just another one-up.