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Revisiting John Mozeliak’s boldest Trade Deadlines 

August 3, 2025 by Viva El Birdos

MLB: Toronto Blue Jays at St. Louis Cardinals
Jeff Curry-Imagn Images

As the Cardinals embrace a new direction, we look back at the high-impact trades that shaped John Mozeliak’s tenure.

With the St. Louis Cardinals trades of Ryan Helsley, Steven Matz, and Phil Maton this season, John Mozeliak seems poised to make his exit with one of the busier trade deadlines I can remember from him. While the returns were modest—prospects like Blaze Jordan and Mason Molina, plus some international pool money—the volume and timing of the moves signaled something rare: a front office finally committing to a direction (ORSTLcardsfan breaks the deadline down here).

Mozeliak, long known for his measured approach, didn’t swing for the fences this time. But the flurry of deals marked a clear pivot toward the future, and perhaps a quiet farewell from the architect of the 2011 championship roster. With that in mind—and maybe as a little homage to Mo—I wanted to look back on some of his more aggressive trade deadlines over the years.

2023: The Soft Sell That Sparked a Reset

While not aggressive in the traditional sense, the 2023 deadline marked a philosophical shift. It was the first time in recent memory the Cardinals felt like sellers at a deadline. Mozeliak traded Jack Flaherty, Jordan Hicks, Paul DeJong, and others for prospects, acknowledging the team’s struggles and pivoting toward a rebuild. It was a move that set the stage for the more decisive actions we saw in this season.

2022: Montgomery & Quintana Reinforce the Rotation

Mozeliak flipped fan-favorite Harrison Bader to the Yankees for Jordan Montgomery and added José Quintana from the Pirates. It was a rare moment of deadline aggression aimed at stabilizing a shaky rotation. Montgomery, in particular, delivered down the stretch and helped the Cardinals clinch the NL Central.

2009: Matt Holliday Comes to Town

In a bold midseason push, Mo sent three prospects—including top slugger Brett Wallace—to Oakland for Matt Holliday. It was a rental at the time, but Holliday re-signed and became a franchise cornerstone. The move signaled a win-now mentality and helped solidify the middle of the lineup for years. A Pujols and Holliday back-to-back — that’s pretty awesome.

2011: The Colby Rasmus Blockbuster

Mozeliak traded away one of the team’s most promising young outfielders, Colby Rasmus, in a multi-player deal that brought in Edwin Jackson, Octavio Dotel, Marc Rzepczynski, and Corey Patterson. It was a gutsy move that prioritized pitching depth over long-term upside—and it paid off. The Cardinals rode that revamped staff and some well-timed squirrel appearances — all the way to a World Series title.

Like many long-tenured executives, Mozeliak’s legacy resists easy definition. It’s marked by restraint, but also by moments of boldness that reshaped the course of Cardinals history. When he went bold, it often altered the Cardinals’ trajectory for better, more often than not. As fans, we’ve been pretty lucky that his biggest swings usually landed.

Happy Sunday!

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