Landing Veteran Pitchers from Cardinals Already Pay Off for Brewers

When the Milwaukee Brewers approached the St. Louis Cardinals in early August about the availability of veteran pitchers Dustin May and JoJo Romero, they had nights like Monday squarely in mind.

A starter throughout his career, May was the first pitcher used out of the Milwaukee bullpen on Monday night when Logan Henderson was pulled from the game after just four innings of work. Facing his former team, May tore through the Dodgers and pitched a scoreless fifth inning while striking out a batter.

In the sixth inning, the Brewers strategically deployed Romero so that he could face Dodgers superstar Shohei Ohtani. Using his sharp-breaking slider, Romero has dominated his regular-season matchups against Ohtani – a driving force behind why the Brewers wanted the lefty in the playoffs. The four-time Most Valuable Player is just 1 for 8 against Romero, with four of those at bats ending in strikeouts.

In Monday’s sixth inning, Romero once again fooled Ohtani with a sweeping slider that was well off the plate. Ohtani tried checking his swing, but he failed for another strikeout.

Romero then struck out catcher Will Smith and got dangerous left-hander Max Muncy to ground out to second base to get out of the sixth inning. When Williams Contreras drove in David Hamilton for the go-ahead run in the bottom of the sixth inning, Romero was in position to earn the first postseason victory of his MLB career.

To give themselves the best shot possible of unseating the back-to-back champion Dodgers, the Brewers acted proactively in adding as many proven arms as they could stockpile to match the firepower of Los Angeles. They did just that – even if it meant trading with the National League Central Division-rival Cardinals and also surrendering two of their prized Minor League prospects.

Holding the leverage in the deal, Cardinals president of baseball operations Chaim Bloom was able to turn the expiring contracts of May and Romero into 18-year-old outfielder Alexander Frias and 22-year-old outfielder Josiah Ragsdale. Frias, who was signed to a $350,000 signing bonus out of the Dominican Republic in January of 2025, is already ranked No. 5 in the Cardinals Minor League system. Ragsdale, a New Jersey native, reached Double-A Springfield by the end of the season and is the No. 11-ranked prospect for the Cards.

Both Frias and Ragsdale possess a rare combination of speed and power and showed it in 2026. Frias played 86 games in the Milwaukee and St. Louis systems, and hit .314 with 20 doubles, five triples, 10 home runs, 73 RBI and 25 stolen bases. The 6-foot-2 slugger has a long, looping swing and he had four doubles, a triple and two homers in 25 games after joining Class-A Palm Beach. Frias is already back in camp with other Cardinals prospects, participating the club’s six-week Fall Off-Season Program in Jupiter, Fla.

Ragsdale dominated play at High-A and Double-A, joining the exclusive 20-double, 20-homer, 20-stolen base club. The former college star at Iona and Boston College slashed .295/.418/.536/.954 with 25 doubles, three triples, 24 homers, 65 RBI and 37 stolen bases in 116 games.

Could it be the rare win/win trade for a Milwaukee team trying to win its first World Series crown and a rebuilding Cardinals franchise trying to get back into contention to win their 12th?