The trade between the St. Louis Cardinals and the Baltimore Orioles involving pitcher Jack Flaherty has become a frustrating reminder that not every deadline move works out the way teams expect. What once looked like a potentially beneficial deal for both organizations has gradually turned into a disappointing outcome on each side, with neither franchise receiving the long-term payoff it hoped for.
When the Cardinals traded Flaherty during the 2023 MLB season, the organization was in a difficult position. Just one year earlier, St. Louis had been viewed as one of baseball’s more complete teams. The club finished the 2022 campaign with a strong 93-69 record and captured plenty of national attention thanks to the memorable farewell season of Albert Pujols, whose pursuit of 700 career home runs energized both the fanbase and the league.
However, the optimism surrounding the franchise disappeared quickly in 2023. Injuries, inconsistency, and underperformance across the roster pushed the Cardinals into one of their worst seasons in recent memory. Instead of competing for another division title, the team struggled throughout the year and eventually finished last in the National League Central with a 71-91 record.
Because of the disappointing season, the Cardinals shifted their focus toward the future before the trade deadline. Veteran and expiring-contract players suddenly became trade candidates as the organization attempted to collect younger talent and reset the roster. Among the most notable names moved were Jordan Montgomery, Jordan Hicks, and Flaherty.
At the time, trading Flaherty seemed understandable. The former ace had shown flashes of brilliance earlier in his career but had also battled injuries and inconsistency. Since he was approaching free agency, St. Louis risked losing him for nothing if they kept him through the end of the season. The front office believed it was the right opportunity to acquire multiple young players who could eventually contribute at the major-league level.
The Orioles, meanwhile, were in a much different situation. Baltimore was emerging as one of the American League’s fastest-rising teams and needed pitching help for a postseason push. The organization hoped Flaherty could stabilize the rotation and provide valuable innings during the second half of the season.
To complete the deal, Baltimore sent infielder César Prieto, left-handed pitcher Drew Rom, and right-handed pitcher Zack Showalter to St. Louis. On paper, the trade appeared balanced enough. The Orioles received a veteran starter with playoff potential, while the Cardinals added three younger players who could help during the club’s transition period.
But almost immediately, the trade began trending in the wrong direction for Baltimore.
Flaherty struggled badly after arriving with the Orioles. Instead of becoming a dependable starter, he failed to find consistency and had difficulty controlling opposing lineups. Across nine appearances with Baltimore, he recorded a 6.75 ERA in just 34 2/3 innings. His performances often put the Orioles in tough situations, and he never truly settled into a reliable role before the season ended.
For a team with postseason aspirations, the lack of production from Flaherty was a major disappointment. Baltimore acquired him hoping he would strengthen the rotation during an important stretch of the season, but the move ultimately provided little impact. Considering the Orioles gave up three young players in the deal, the return fell far short of expectations.
Still, while Baltimore failed to gain meaningful value from Flaherty, the Cardinals have not exactly emerged as winners either.
Of the three players St. Louis acquired, Prieto is currently the only one still contributing within the organization. The infielder has shown some promise offensively, particularly at the Triple-A level, where he produced strong numbers and earned opportunities in the majors. However, his role at the major-league level has largely been limited to a bench position rather than becoming an everyday starter.
Prieto still has time to develop into a larger contributor, but at this stage, he has not become the type of impact player that would significantly change perceptions of the trade.
The other two pieces acquired by St. Louis have already moved on from the organization. Drew Rom eventually landed in the Milwaukee Brewers farm system, while Zack Showalter was recently released entirely. Losing two-thirds of the return package so quickly highlights just how little value the Cardinals ultimately gained from moving Flaherty.
That reality makes the deal especially frustrating for St. Louis fans. Although Flaherty was no longer performing at an elite level at the time of the trade, he was still a recognizable starting pitcher with upside and experience. The hope was that the Cardinals could at least secure multiple prospects capable of contributing meaningfully in future seasons.
Instead, the organization is left with one reserve infielder and very little else to show for the transaction.
Trades like this often demonstrate how unpredictable baseball can be. At the deadline, teams operate under pressure to improve either the present or the future, and many deals look reasonable based on the information available at the time. In this case, both sides had understandable motivations. Baltimore wanted pitching for a playoff race, while St. Louis wanted younger talent during a disappointing season.
Unfortunately, neither plan worked out.
Flaherty failed to deliver the boost Baltimore expected, and the prospects sent to St. Louis have not developed into major building blocks. Years later, the trade now looks like one of those rare lose-lose scenarios where both organizations walk away unsatisfied.
For the Orioles, the trade serves as a reminder that rental players can be risky investments, especially when a pitcher is struggling with consistency. For the Cardinals, it highlights the importance of maximizing value when selling at the deadline, particularly when moving recognizable talent.
As time continues to pass, the Flaherty trade increasingly feels like a missed opportunity for both clubs. Neither franchise gained the long-term advantage it hoped for, and the deal has gradually become an example of how quickly a seemingly logical trade can age poorly in Major League Baseball.
