St. Louis Cardinals’ Jack Flaherty Trade: A Deal That Hasn’t Paid Off for Either Side

The 2023 season was a disaster for the St. Louis Cardinals, marking one of their worst seasons in recent memory. After an exciting 2022 campaign where they finished 93-69 and garnered plenty of attention due to Albert Pujols’ chase for 700 career home runs, the Cardinals crashed hard in 2023. They finished last in the National League Central with a dismal 71-91 record, which kicked off what looks like a prolonged rebuilding period. While 2026 is still technically a part of this rebuild, there have been some positive moments that suggest the future may hold more promise.

However, when reflecting on 2023, one of the biggest moments was the Cardinals’ decision to become major sellers at the trade deadline. Among the players traded were key figures like Jordan Montgomery, Jack Flaherty, and Jordan Hicks. The trade involving Flaherty, in particular, has raised questions, as it appears to have been a poor decision for both sides.

The Flaherty Trade: A Miss for Both Teams

The St. Louis Cardinals traded Jack Flaherty, who was set to become a free agent after the 2023 season, to the Baltimore Orioles in exchange for infielder César Prieto, left-handed pitcher Drew Rom, and right-handed pitcher Zack Showalter. Looking back, it’s safe to say that the deal hasn’t worked out well for either team.

Flaherty pitched in just nine games for Baltimore, posting a disappointing 6.75 ERA over 34.2 innings. He showed little of the potential that once made him a key figure for the Cardinals’ rotation. While his time in Baltimore wasn’t a complete disaster, it certainly didn’t yield the expected results for the Orioles.

But the Cardinals’ return for Flaherty hasn’t been any better. Of the three players they acquired, only César Prieto remains with the team, and he’s currently a bench piece in St. Louis after performing decently in Triple-A. While it’s positive that Prieto has contributed at the major league level, the Cardinals have struggled to make the most of the other pieces they received.

The Decline of Zack Showalter and Drew Rom

In a troubling development, the Cardinals made the decision to release Zack Showalter, one of the prospects they received in the trade, in early May 2026. Showalter had been a part of the deal that sent Flaherty to Baltimore, but after struggling to find a spot in the Cardinals’ system, he was cut loose. As a result, he is now a free agent, leaving the Cardinals with only Prieto as a direct return from the trade.

Drew Rom, another piece in the deal, has not fared much better. Rom is currently in the Milwaukee Brewers’ farm system, far removed from his time as a prospect with the Cardinals. The fact that Rom is no longer part of St. Louis’ plans underscores the lack of success this trade has yielded.

A Deal That Went Wrong for Both Sides

At the time of the trade, Jack Flaherty was viewed as a promising, albeit inconsistent, starting pitcher with a lot of potential. The Cardinals thought they were making a smart move by trading him for what they hoped would be three solid prospects. Fast forward to 2026, and the deal has not paid off.

For the Cardinals, two of the three players they received—Showalter and Rom—are no longer with the organization, and Prieto, while still in the majors, is limited to a bench role. It’s a far cry from the potential they envisioned when making the trade.

Meanwhile, the Orioles, who were hoping Flaherty would help bolster their pitching staff, got very little out of the trade. Flaherty’s lackluster performance in Baltimore leaves them with little to show for their effort, as his brief tenure did not impact their postseason aspirations in a meaningful way.

A Poorly-Aged Trade for the Cardinals

The Jack Flaherty trade is the perfect example of a deal that has aged poorly. The Cardinals traded away a starting pitcher with potential and received three prospects in return, but only one of them remains with the team, and he is a fringe player at best. This is the type of trade that makes you question the front office’s decision-making and ability to capitalize on valuable assets.

For the Orioles, while they didn’t give up much to acquire Flaherty, they also didn’t receive much in return, making the deal a wash for them as well. It’s a lose-lose situation, with neither side coming out as a clear winner.

In the end, the trade didn’t benefit either team, and it’s one of those moves that will be remembered as a mistake for both sides. The Cardinals, as they continue to rebuild, will need to make smarter trades if they hope to regain their competitive edge in the coming years. The Flaherty trade, in hindsight, will likely be seen as one of the low points in a difficult period for St. Louis.