Roundtable Sports' John Denton thinks former Cardinals ' pitcher Lance Lynn was right to wonder if the club should consider trading Masyn Winn for pitching and moving JJ Wetherholt to shortstop.
During his seven seasons with the Cardinals over two stints, right-handedpitcher Lance Lynn was largely known for being a part of the 2011 World Serieschampionship team as a tough-minded rookie, piling up incredible success whenpitching at Busch Stadium and being someone always willing to stir the proverbialpot with his sometimes controversial, pointed comments.
Lynn, who announced his retirement in April of 2025following a 13-year MLB career where he went 143-99, raised some eyebrows this weekend while speculating about Gold Gloveshortstop Masyn Winn's future in St. Louis during an appearance on the CardinalTerritory podcast.
Lynn, who wrapped his playing career up with Cardinals in2024, wondered if the club might be willing toshop the 24-year-old Winn before the Aug. 3 MLB Trade Deadline to see if hecould bring back a top-of-the-rotation starter in return. Lynn's basis for theargument was the Cardinals' refusal in recent years to sign Winn to a contractextension and instead ink second baseman/shortstop JJ Wetherholt to aneight-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 rotationacquired in a deal involving Winn?
"I make this move only if I think this: 'Do I think JJcould play a shortstop every day that I can get away with trading Masyn Winnfor something that is really forward moving on the pitching side?'" Lynn askedon the podcast appearance with host Jim Hayes on Friday. "That's a (decision of), 'Hey, I canget 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 atshortstop in 2025 after committing just three errors in 501 total chances, hasmostly struggled at the plate this season while also seeing some regression inhis defense. Winn heads into Sunday's series finale against the Reds slashingjust .235/.311/.316/.627 with 12 doubles, four homers and 42 RBI. His OPS+ for2026 is 79, meaning his production is 21 percent below average for players athis position. Winn's career OPS+ of 88 is also below average for an MLB shortstopat the plate.
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Defensively, he was meshed well with Wetherholt at secondbase and the two of them have combined to turn 50 double plays. Winn hasn'tbeen as consistent defensively as 2025, committing eight errors in 308 totalchances. Whereas he ranked second among all MLB shortstops in Outs AboveAverage in 2025 (21), he has fallen to seventh among MLB shortstops (nine) inthat defensive metric in 2026.
After having arthroscopic knee surgery last September, Winnhoped 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 MLBseason when he hit .267 with a .730 OPS, 32 doubles, 15 home runs and 57 RBI asthe Cardinals' leadoff hitter.
However, Winn got off to an awful start at the plate in2025, was dropped to the lower third of the batting order and has never seemedto recover as a hitter. Over his 3/12-year MLB career – one that has seen himplay through back pain and injuries to both knees – Winn is a .248 hitter withan .305 on-base percentage and a .667 OPS.
What impact has no extension had on Winn?
Lynn wondered what impact the lack of a contract extensionmight have had on Winn's focus in recent years.
"I don't know where Masyn's head's at with not being theleadoff guy and not gaining an extension," Lynn said on Cardinal Territory. "Wecan say everything we want about, 'Hey, I'm good with everything,' but yourfeelings get hurt when you think you're the next guy in line to be the leadoffguy and an extension and you've gotten neither and someone else (Wetherholt) hasthat was a rookie when they showed up. That's a slap in the face and I don'tcare what anyone else says."
Wetherholt, 23 and a leading candidate to win the NL'sRookie of the Year award, earned his nine-figure contract extension afterslashing .256/.353/.398/.751 with 10 doubles, 15 home runs, 40 RBI and 10steals without being caught in 99 games. He's compiled a 4.2 WAR and a 113OPS+, meaning he's produced at a 13 percent clip higher than the average secondbaseman.
Defensively, Wetherholt has put himself in line for a GoldGlove as a rookie, something only one rookie in the rich history of theCardinals ( Brendan Donovan in 2022) has done. He's committed just two errors in97 games at second base. He's appeared as shortstop in three games and he hasnot committed an error in 11 chances.
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Lynn wonders if Wetherholt's favorable small sample size atshortstop might be enough for the Cardinals to shop their Gold Glove winner atthat position for pitching? After all, the Cardinals' actions have spokenloudly 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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