During his seven seasons with the Cardinals over two stints, right-handed pitcher Lance Lynn was largely known for being a part of the 2011 World Series championship team as a tough-minded rookie, piling up incredible success when pitching at Busch Stadium and being someone always willing to stir the proverbial pot with his sometimes controversial, pointed comments.

Lynn, who announced his retirement in April of 2025 following a 13-year MLB career where he went 143-99, raised some eyebrows this weekend while speculating about Gold Glove shortstop Masyn Winn’s future in St. Louis during an appearance on the Cardinal Territory podcast.

Lynn, who wrapped his playing career up with Cardinals in 2024, wondered if the club might be willing to shop the 24-year-old Winn before the Aug. 3 MLB Trade Deadline to see if he could bring back a top-of-the-rotation starter in return. Lynn’s basis for the argument was the Cardinals’ refusal in recent years to sign Winn to a contract extension and instead ink second baseman/shortstop JJ Wetherholt to an eight-year extension that could be worth as much as $132 million.

Would the Cards be better off, Lynn wondered on the podcast, with Wetherholt at shortstop and a top pitching prospect in the rotation acquired in a deal involving Winn?

“I make this move only if I think this: ‘Do I think JJ could play a shortstop every day that I can get away with trading Masyn Winn for something that is really forward moving on the pitching side?’” Lynn asked on the podcast appearance with host Jim Hayes on Friday. “That’s a (decision of), ‘Hey, I can get maybe a top three rotation (pitcher) or a top one or a two (ranked starter) from a team (in exchange for Winn).’”

Winn, who won the National League Gold Glove award at shortstop in 2025 after committing just three errors in 501 total chances, has mostly struggled at the plate this season while also seeing some regression in his defense. Winn heads into Sunday’s series finale against the Reds slashing just .235/.311/.316/.627 with 12 doubles, four homers and 42 RBI. His OPS+ for 2026 is 79, meaning his production is 21 percent below average for players at his position. Winn’s career OPS+ of 88 is also below average for an MLB shortstop at the plate.

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Defensively, he was meshed well with Wetherholt at second base and the two of them have combined to turn 50 double plays. Winn hasn’t been as consistent defensively as 2025, committing eight errors in 308 total chances. Whereas he ranked second among all MLB shortstops in Outs Above Average in 2025 (21), he has fallen to seventh among MLB shortstops (nine) in that defensive metric in 2026.

After having arthroscopic knee surgery last September, Winn hoped to run more in 2026, but he has just stolen eight bases in 10 tries. Also, he’s struck out 76 times compared to just 34 walks.

Winn seemed headed for stardom following his first full MLB season when he hit .267 with a .730 OPS, 32 doubles, 15 home runs and 57 RBI as the Cardinals’ leadoff hitter.

However, Winn got off to an awful start at the plate in 2025, was dropped to the lower third of the batting order and has never seemed to recover as a hitter. Over his 3/12-year MLB career – one that has seen him play through back pain and injuries to both knees – Winn is a .248 hitter with an .305 on-base percentage and a .667 OPS.

Lynn wondered what impact the lack of a contract extension might have had on Winn’s focus in recent years.

“I don’t know where Masyn’s head’s at with not being the leadoff guy and not gaining an extension,” Lynn said on Cardinal Territory. “We can say everything we want about, ‘Hey, I’m good with everything,’ but your feelings get hurt when you think you’re the next guy in line to be the leadoff guy and an extension and you’ve gotten neither and someone else (Wetherholt) has that was a rookie when they showed up. That’s a slap in the face and I don’t care what anyone else says.”

Wetherholt, 23 and a leading candidate to win the NL’s Rookie of the Year award, earned his nine-figure contract extension after slashing .256/.353/.398/.751 with 10 doubles, 15 home runs, 40 RBI and 10 steals without being caught in 99 games. He’s compiled a 4.2 WAR and a 113 OPS+, meaning he’s produced at a 13 percent clip higher than the average second baseman.

Defensively, Wetherholt has put himself in line for a Gold Glove as a rookie, something only one rookie in the rich history of the Cardinals (Brendan Donovan in 2022) has done. He’s committed just two errors in 97 games at second base. He’s appeared as shortstop in three games and he has not committed an error in 11 chances.

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Lynn wonders if Wetherholt’s favorable small sample size at shortstop might be enough for the Cardinals to shop their Gold Glove winner at that position for pitching? After all, the Cardinals’ actions have spoken loudly with where they have invested their money over the next eight seasons.  

“You have a serviceable shortstop who you just gave a $100-plus million to … that’s what I’m saying,” Lynn said with a wry smile.

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