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MLB Trade Fails That Will Hurt Teams in 2023

Henry Hansen

Mookie Betts celebrates after hitting a home run for the Los Angeles Dodgers on May 25, 2022.


The most notorious trading flop in baseball history is one that is known by everyone, whether they meticulously follow baseball or not. On January 5, 1920, a seemingly mediocre pitcher was given to the New York Yankees, a trade that would spark one of the most famous sports rivalries of all time, and haunt the Boston Red Sox until almost a century later. This trade, of course, concerns the legendary Babe Ruth, who upon arriving to the Yankees, began an entirely new era of home-run hitting.


In today’s age, influential trades occur constantly and can cause seasons to be ruined and careers to be broken––all due to poor management. Take, for example, the Boston Red Sox’s trade of Mookie Betts to the Los Angeles Dodgers. Betts was sent to Dodgers on February 10, 2020, which may seem like a long time ago, but both teams are still feeling the effects now. Betts played a top-notch, consistent game throughout the 2022 season, hitting 35 home runs and making the all-star team for the sixth time. His fielding was solid, as usual, and he received his 5th Fielding Bible Award for the best defensive right fielder of the year. On the other hand, the Red Sox had their worst year since 2015, with a winning percentage of 0.481. It seems as though the Red Sox giving up Betts in order to gain some younger stars, such as prospects Connor Wong and Jeter Downs, really cost them.


A more recent trade, just after the all-star break of 2021, gave the Yankees an excellent addition to their pitching roster. Clay Holmes, an amazing closer, was traded by the Pittsburgh Pirates for Diego Castillo and Hoy Park. Holmes had his first all-star appearance last season and finished with a 2.54 earned run average (ERA). In his previous years on the Pirates, he had a 6.84 ERA in 2018, and a 5.58 ERA in 2019. Although the Pirates weren’t able to predict that Holmes would be able to take his sinker to a whole new level, they certainly got the short end of the stick in the trade by losing him.


And yet, what comes around goes around, and the Yankees learned that the hard way. In a deal finalized right before the 2022 trade deadline, the Yankees decided to give the St. Louis Cardinals starter, Jordan Montgomery, in return for Harrison Bader, a center fielder. Bader certainly delivered in the postseason––hitting 0.333 and going long five times––but losing Montgomery struck the Yankees hard. Montgomery won six games in 63 days with an ERA of 3.11 with the Cardinals, after previously only winning three in 137 days. Something must have clicked in Montgomery because he pitched like an entirely different person after the trade.


It can be challenging for baseball organizations to foresee how a player may do after a trade, and sometimes teams just get unlucky. They all essentially took a gamble as they believed their decisions would pay off, but ultimately, they were far worse off because of it.



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