A difficult offseason lies ahead for the St. Louis Cardinals. Chaim Bloom embraced the long view last winter, shedding excess salary and restoring depth to a depleted farm system. Now, the Cardinals are ahead of schedule. St. Louis is technically still in the Wild Card race, although next season seems more realistic for a proper breakthrough.
With such rapid improvement comes heightened expectations. Cardinals fans typically aren't the most patient bunch. The core of this roster, from Rookie of the Year candidate J.J. Wetherholt to sluggers Alec Burleson and Jordan Walker, is very solid. But in order to take that next step, St. Louis will need to make sacrifices.
One potential casuality: Gold Glove shortstop Masyn Winn, whom the Cards could "look to move" in the offseason, per FanSided's Pat Ragazzo. Winn has experienced back-to-back sluggish seasons at the plate and Wetherholt, who inked a $112.5 million extension this year, is a natural shortstop. Let's map out what a Winn trade could look like.
Cardinals trade Masyn Winn to Braves for young pitching

Shortstop remains a primary position of need for the Braves, whose lineup is otherwise rock solid. The Ha-Seong Kim experiment blew up in their faces this season, while 25-year-old prospect Jim Jarvis failed to perform when called up. Ozzie Albies is also a potential free agent this winter if the team declines his option amid yet another second-half swoon, so the Braves' middle infield setup could become even more of an open sore.
While Winn's bat is a concern, he compensates with consistently elite defense at a critical position. He's arguably the best infield defender in the Majors, with 18 outs above average this season (in the 99th percentile) and the capacity for triple-digit velocity on throws to first base. The Braves would benefit immensely from the high floor Winn sets with his glove.
For the Cardinals, this is a chance to add two impactful young arms. The Braves flirted with handing 22-year-old Owen Murphy a rotation spot this season, although he never quite seized the opportunity. Still, he pounds the strike zone with an effective fastball and generates frequent chases on his changeup and slider. Murphy put up a solid 3.07 ERA in 18 Triple-A starts this season and could contribute immediately to a needy Cardinals rotation.
The real gem of this return, however, is 21-year-old Didier Fuentes. After struggling in past starting cameos for the Braves, Fuentes has blossomed in a bullpen role this season. He has a 2.21 ERA and 1.05 WHIP with 88 strikeouts in 69.1 innings. St. Louis can explore stretching Fuentes back out to a starter's workload, but he'd also immediately become the best reliever on the Cardinals roster. If St. Louis can lock him in as a shutdown closer, under club control through 2031, that's a huge boon for a team that has struggled to preserve leads down the stretch.
Cardinals trade Masyn Winn to Yankees for ex-top prospect

The Yankees' lack of fundamental soundness on the defensive end has bitten them in the you-know-what all season, just like it did last year. The hope was that top prospect George Lombard Jr. could steady the ship at shortstop, but he has stacked up errors left and right. It's too early to write off the 21-year-old long term, but he could serve more comfortably at third or second — which is notable, since Jazz Chisholm Jr. is about to free agency.
Winn immediately alleviates a ton of defensive issues for the Yankees, while his weaker bat would be well-protected in the American League's most potent lineup. New York has the resources to one day pay Winn his worth, too, although three additional years of club control means those conversations are in the distant future.
This move allows St. Louis to bump Wetherholt to shortstop and plug in former top prospect Anthony Volpe at second base, where he has looked much more solid of late in New York. Volpe is a former Glod Glove shortstop whose defensive profile is very much salvagable, especially at a less demanding position. He's also a hitter with more upside right now, with the potential to add real pop to the back half of St. Louis' lineup.
The Cardinals also add high-leverage reliever Brent Headrick, with a 1.94 ERA and five years of club control, and 24-year-old southpaw Kyle Carr, a Triple-A arm who profiles as a potential back-end starter with plus command.
Cardinals trade Masyn Winn to Dodgers for power arms

The Dodgers don't need the extra help, but L.A.'s infield has become a point of concern this season. Mookie Betts is still a phenomenal defender almost anywhere on the diamond, but it could behoove Los Angeles to move him to a less burdensome position. The Dodgers can upgrade at second base and add an all-world shortstop in one fell swoop, trading from their unmatched depth to get a deal across the finish line.
Edgardo Henriquez is already one of the most dominant relievers in baseball at 24 years old, but the Dodgers have a lot of money and talent wrapped up in the bullpen. The Cardinals would value Henriquez more as a potential long-term closer with triple-digit velocity and an elevated soft contact rate.
Emmet Sheehan has gradually phased out of the Dodgers' rotation this season, but that's more a factor of L.A.'s wealth of talent than any lack of ability. Sheehan has struggled, yes, with a 4.79 ERA and 1.22 WHIP in 107.0 MLB innings, but the 26-year-old is a single season removed from posting a 2.82 ERA in 15 appearances (12 starts) and pitching important bulk innings in the playoffs. Sheehan's underlying metrics lay the groundwork for positive regression (3.72 expected ERA); he could end up as a front-line member of the Cards rotation in the coming years, under club control through 2029.
