I think it’s safe to say that most St. Louis Cardinals fans are anxious to identify the next St. Louis Cardinals core group of players you rebuild around. Once identified, you would hope to lock those players into long-term extensions. If you were St. Louis Cardinals President of Baseball Operations Chaim Bloom, would you work to extend shortstop Masyn Winn? Would your answer be now, later or never?
The St. Louis Cardinals still have four years of team control as he’s currently on a trajectory to reach free agency after the 2029 season, but he’s eligible for arbitration after the upcoming 2026 season. Fangraphs has Masyn pinned as a 3.6 WAR while ZIPS projects him with a 3.1 WAR for the 2026 season. His elite defensive skills have already been rewarded as a Gold Glove finalist in 2024 and a Gold Glove winner in 2025. Offensively, Masyn had a solid 2024 slashing a .267 average with 15 home runs and an OPS of .730, but was hampered by nagging injuries in 2025 with his average dipping to .253, 9 home runs and an OPS of .673.
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What would a Masyn Winn extension look like? As I shared a few weeks ago, it’s believed that an extension at this point in his career would be somewhere in the neighborhood of 8 years for around $100 million dollars. My initial reaction to that number and those years is I would jump at the chance if I were Chaim Bloom and Masyn Winn’s agent Andrew Guerra said yes. The cynical side of me says that I would wait at least one more year to see what Masyn’s performance is like now that the torn meniscus in his right knee has been surgically repaired. That would be the reason for a potential “later” answer.
The X factor for me is Masyn Winn’s maturity and potential team leadership role. He addressed that during the Winter Warmup a few weeks ago. He said that he specifically wanted to help JJ Wetherholt adjust to the major leagues.
Masyn Winn – “As far as…leadership…it’s something I take pride in. I’m gonna go out there and compete and play how I play…I’m really looking forward to playing with JJ…I want him to be himself…I want him to go out there and have some fun…I wanna be there for JJ and let him be great.”
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I’ve seen enough of Masyn Winn to know that I want him to be a part of the new St. Louis Cardinals core, but I understand those who want to see more before they would offer an extension. What’s your opinion? Now, later or never?