Cardinals' rekindling of negotiations with rival Brewers quashes 11-year trade drought

It required a bit of waiting, but the St. Louis Cardinals have finally executed their first deal of the 2026 trade deadline, trading starting pitcher Dustin May and relief pitcher JoJo Romero for outfield prospects Alexander Frias and Josiah Ragsdale. The most notable facet of the trade, though, was the Cardinals' partner in this tango, as the two pitchers are headed to the division rival Milwaukee Brewers in the first deal between the teams since 2015.

Jeff Jones posted on X that the last trade between St. Louis and Milwaukee involved the Brewers sending veteran relief pitcher Jonathan Broxton and cash to the Cardinals for minor league outfielder Malik Collymore. Broxton had pitched to a 5.89 ERA in 36.2 innings prior to the trade, but the Cardinals saw some bright spots under the hood, such as his 3.71 FIP, and opted to take a flier on the then-31-year-old veteran.

The Cardinals needed bullpen reinforcements down the stretch, as setup man Seth Maness had faltered in July, and they had also acquired reliever Steve Cishek earlier that month. The moves paid off, as Broxton pitched to a 2.66 ERA in 23.2 innings and the Cardinals ultimately won the competitive National League Central, holding an impressive 100-62 record and eking out the second-place Pittsburgh Pirates by two games.

The Brewers, meanwhile, were headed nowhere fast and finished fourth in the division, with a 68-94 record. They hoped that Collymore, MLB Pipeline's 27th-ranked Cardinals prospect that season, would bolster their farm system. Collymore had hit .333 with an .883 OPS with the Cardinals' Rookie ball affiliate in 2014 but struggled and hit .216 in 2015 prior to the trade.

Collymore spent just one full season in Milwaukee's system, hitting .167 with a .435 OPS at High-A Brevard County. He finished his professional career in the Cincinnati Reds system and played one season of independent ball with the Ottawa Champions in the Canadian-American Association in 2019 before hanging up his spikes.

The Cardinals ended up on the stronger side of the deal, even though Broxton faltered in 2016 and was downright putrid in 2017 with St. Louis. But since around 2016, the Cardinals and Brewers have drifted in opposite directions regarding player development and talent identification, which could cause Cardinals fans some anxiety with the latest trade.

The Cardinals need to be careful when trading with the Brewers

Trades within the division seem to be all the rage during this deadline: Along with the Cardinals-Brewers swap, the Baltimore Orioles made a deal with the Boston Red Sox; the New York Mets paired off with the Philadelphia Phillies; and the San Diego Padres hammered out a trade with the San Francisco Giants.

Although divisional play is less frequent nowadays with every team playing each other at least once every season, there are still reasons to be wary of intradivisional deals, especially if both teams are competing. That's not the case with the Cardinals, and they seemed to be happy to provide May and Romero, both of whom are on expiring contracts, to the Brewers as Milwaukee races toward the divisional crown.

Bloom's latest trade partner is novel, risky and exciting. The Brewers have made headlines recently for their shrewd moves, such as offloading Caleb Durbin in a deal for a seemingly stagnant former top prospect in Kyle Harrison prior to this season. The Brewers unlocked Harrison's potential, and he is currently among the top pitchers in the National League. In 2022, they grabbed William Contreras in a complex three-team traded that forced them to surrender only outfielder Esteury Ruiz, and those aren't their only clever moves. The Cardinals, meanwhile, were victims of the Randy Arozarena swipe and the Sandy Alcantara swindle.

The Cardinals have since remade their pipeline and overhauled their development staff, and that, combined with Chaim Bloom's more modern approach than that of John Mozeliak, can assuage fans' fears to an extent about a Brewers deal. The trade package that St. Louis received appears enticing at first glance, and maybe these new-look Cardinals can mold Frias and Ragsdale into strong regulars for the next competitive squad.

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