It’s no secret that MLB front offices have become more sophisticated than ever before, with data and advanced analytics shaping nearly every decision. As a result, teams are making fewer major mistakes compared to past decades. This trend is especially evident when you look at some of the prospects traded away in the previous decade (2010-2019). Names like Yordan Alvarez, Max Fried, Zack Wheeler, and Fernando Tatis Jr. all stand out as examples of players who were dealt before reaching their potential, only for those trades to haunt the teams involved. While a few teams managed to win championships in the short term—such as the Cubs with Aroldis Chapman (traded for Gleyber Torres) and the Nationals with Adam Eaton (traded for Lucas Giolito)—most of these moves ultimately did not pay off.

Now, as we reach the midpoint of the 2020s, major trade blunders are fewer and farther between. Top prospects are viewed as highly valuable commodities, often held onto unless absolutely necessary. However, even in this new era of strategic decision-making, mistakes are still made. These errors can come in various forms: poor trades, ill-advised signings, and miscalculations during key moments in the playoffs. Drawing inspiration from ESPN NFL writer Bill Barnwell, we’re looking back at the worst decision each MLB team has made from 2020 to 2024. The focus here is not on the process or the reasoning behind the moves, but rather the outcomes and the lasting impact.

Among the least damaging mistakes in this period, we can see examples from teams like the Baltimore Orioles, Pittsburgh Pirates, and San Francisco Giants. For instance, the Orioles traded away Tanner Scott, a promising relief pitcher, to the Marlins in April 2022. While Scott had struggled with control earlier in his career, he found his groove in Miami, posting stellar numbers in the following seasons. The Orioles, who made significant strides in rebuilding their roster, could have really used Scott in their bullpen, particularly in 2023 when they were in playoff contention. This trade could have been avoided, and Scott might have helped fill the closer role that ultimately went to Craig Kimbrel in 2024.

Similarly, the Pittsburgh Pirates’ selection of Henry Davis with the first overall pick in the 2021 draft has not aged well. While there wasn’t a clear-cut consensus top prospect that year, Davis, a catcher from Louisville, has not lived up to expectations. His struggles at the plate have been evident, with a .144 batting average in 37 games during the 2024 season, and his overall production has been disappointing. In hindsight, players like Jackson Jobe, Marcelo Mayer, or Jordan Lawlar might have been better picks for the Pirates.

Lastly, the San Francisco Giants made a head-scratching decision when they signed outfielder Mitch Haniger to a three-year, $43.5 million contract in December 2022. Haniger, entering his age-32 season, was coming off a rough year in which he played just 57 games and had a history of injuries. The deal was risky for a player with limited speed and a questionable injury history. Even with the best intentions, this move has proven to be a misstep, as Haniger has failed to deliver on the expected production.

Despite the rise of smarter decision-making in MLB, these mistakes remind us that even the most data-driven front offices are not immune to misjudgments. The next few years will likely reveal even more lessons learned and potential regrets from teams trying to navigate the increasingly complex world of modern baseball.