The Red Sox are a team that has had the Cardinals' number in the World Series the past two times they've met on the big stage. Back in 2004, the Red Sox broke their curse by sweeping the Cardinals in the World Series in what may have been one of the worst Fall Classic displays in Cardinals history. Nine years later, Boston was at it again and they knocked out the Cardinals in six games.
At the same time, the Cardinals and Red Sox have made some deals with each other. The most recent ones include the Tyler O'Neill trade from last offseason and the John Lackey trade from a decade ago. There have also been plenty of other players who have played for both franchises, including Joe Kelly, Allen Craig, Jon Lester, and even Cardinals legend Willie McGee.
The most recent Red Sox connection to join the Cardinals is Chaim Bloom. He served as Boston's chief baseball officer from 2020-23 before being added to the St. Louis front office last winter. Based on recent comments from John Mozeliak, Bloom appears to be the heir apparent and may take over as president of baseball operations sooner rather than later.
If that's the case, then Bloom may recruit a few Red Sox connections to join the Cardinals in the offseason. Whether it's players or coaches, there are a few people with Red Sox ties that may find their way to St. Louis. Here are three players and one manager that could join the Cardinals this winter.