2 Costly Mistakes Chaim Bloom Can’t Afford to Repeat With Cardinals

Chaim Bloom will begin a rebuild in St. Louis, but he has to get it right.

May 27, 2022; Boston, Massachusetts, USA; Boston Red Sox president Sam Kennedy and chief baseball officer Chaim Bloom honor former player David Ortiz into the Red Sox Hall of Fame prior to a game against the Baltimore Orioles at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

The 2025-26 MLB offseason marks the start of a brand-new era for the St. Louis Cardinals, as Chaim Bloom officially takes over as president of baseball operations.

For Cardinals fans, it feels like a long-overdue breath of fresh air. After years of frustration under John Mozeliak, St. Louis is turning the page and hoping Bloom can lead them back to the top of the National League Central.

The Cardinals have missed the postseason three straight years and finished below .500 twice in that span — an unacceptable stretch for a franchise with such a proud history. Bloom’s challenge is clear: rebuild the Cardinals into contenders again without repeating the same mistakes that cost him in Boston.

Here are two key lessons Bloom must learn from his Red Sox tenure to ensure St. Louis doesn’t suffer the same fate.

Don’t Trade Stars for Weak Returns

Sep 23, 2025; San Francisco, California, USA; St. Louis Cardinals second baseman Brendan Donovan (33) celebrates his double against the San Francisco Giants during the fifth inning at Oracle Park. Mandatory Credit: Eakin Howard-Imagn Images | Eakin Howard-Imagn Images

One of the biggest blemishes on Bloom’s time with the Boston Red Sox was the 2020 trade of Mookie Betts to the Los Angeles Dodgers, a move that still stings in New England.

At the time, Boston was eager to shed salary, but the return package failed to deliver any long-term value. Of the players Boston acquired, only Connor Wong remains on the roster five years later.

If Bloom decides to move a player like Brendan Donovan or another core piece in St. Louis, he must make sure the Cardinals get true impact talent in return — players who can help both now and in the future.

Cardinals fans have seen this franchise trade away talent before and can’t afford another deal that sets the team back for years. This time, Bloom needs to maximize every trade chip and prioritize quality over quantity.

Don’t Miss Opportunities to Extend Key Players

Sep 6, 2025; St. Louis, Missouri, USA; St. Louis Cardinals shortstop Masyn Winn (0) throws to first base against the San Francisco Giants at Busch Stadium. Mandatory Credit: Tim Vizer-Imagn Images | Tim Vizer-Imagn Images

Another costly mistake Bloom made in Boston was failing to extend Xander Bogaerts before the 2022 season. Bogaerts eventually walked in free agency, leaving a massive hole in the Red Sox lineup — and in their leadership core.

While Bloom is known for being conservative with long-term deals, that approach can hurt when it comes to keeping homegrown stars. The Cardinals may not have a current superstar like Bogaerts, but young players such as Masyn Winn, Alec Burleson, and Iván Herrera could be part of the next great St. Louis core.

Bloom should be proactive about locking up key players early on team-friendly extensions before they reach free agency. Keeping young, controllable talent in St. Louis will be vital if the Cardinals want to stay competitive long-term.

For Cardinals fans, there’s reason for optimism. Bloom has proven he can build sustainable organizations and develop young talent — something the Cardinals desperately need after several underwhelming seasons.

But to succeed in St. Louis, Bloom must learn from his past and avoid the same pitfalls that derailed his tenure in Boston. If he can balance patience with smart aggression, he has a chance to bring the Cardinals back to relevance — and earn the trust of a passionate fan base eager to see winning baseball return to Busch Stadium.

More MLB: Chaim Bloom's Trade Decisions Won't Be Easy With Cardinals