The most painful thing anyone can experience, save for maybe a paper cut, is the bite of a Major League Baseball trade gone wrong.

Need examples? We got 'em.

We've recalled 15 trades—some of which we've lumped together for [waves hands] reasons—from recent years that have turned disastrous for one team and which will likely be just as bad, if not worse, in 2023. These concern the surrendering of players who were unproven or even on a downswing at the time but who have since realized or reclaimed stardom.

Expecting to read about the trades of Manny Machado from 2018 or of Mookie Betts from 2020? Well, don't. Both may be notorious flops, but the club control that the Baltimore Orioles and Boston Red Sox were trading at the time has long since run out. It's therefore disingenuous to wonder what things would be like if they still had Machado and Betts today.

We'll start with some dishonorable mentions before hitting on some multiple-for-one specials, and then we'll check others off one at a time in chronological order.


Dishonorable Mentions

Chicago White Sox: The James Shields-Fernando Tatís Jr. Trade

The Deal (June 4, 2016): Chicago White Sox get RHP James Shields (minus-0.3 WAR); San Diego Padres get SS Fernando Tatís Jr. (13.6), RHP Erik Johnson (minus-0.6)

This looked like an all-time blunder for the White Sox as Tatís was going off for a 160 OPS+, 81 home runs and 52 stolen bases between 2019 and 2021. But following his suspension and multiple surgeries in 2022, one now has to wonder if the worst has past for the Pale Hose.


Miami Marlins: The Dan Straily-Luis Castillo Trade

The Deal (Jan. 19, 2017): Miami Marlins get RHP Dan Straily (1.9 WAR); Cincinnati Reds get RHP Luis Catillo (18.3), RHP Austin Brice (minus-0.5), OF Zeek White (0)

Former Marlins president David Samson says he would do this one again, for whatever that's worth. For our part, we sided against giving it the full-bash treatment because today's Marlins have so much pitching that they were able to sacrifice Pablo López for Luis Arráez just last week.


Seattle Mariners: The David Phelps-Pablo López Trade

The Deal (July 20, 2017): Seattle Mariners get RHP David Phelps (0.2); Miami Marlins get RHP Pablo López (8.5), RHP Lukas Schiraldi (0), RHP Brandon Miller (0), OF Brayan Hernandez (0)

López was indeed traded for a middling pitcher in his own right, as Phelps was a good-not-great relievers at the time, and he ultimately made just 10 appearances for Seattle. The Mariners are nonetheless in the same boat as the Marlins in having too much pitching to really fret about it.


Los Angeles Dodgers: The Tony Watson-Oneil Cruz Trade

The Deal (July 31, 2017): Los Angeles Dodgers get LHP Tony Watson (0.4 WAR); Pittsburgh Pirates get SS Oneil Cruz (2.4), RHP Angel German (0)

This, of course, depends on how Cruz continues to develop. But if he starts getting bat to ball more frequently, his other eye-popping tools may well turn him into the kind of star that the Dodgers would probably prefer to have at shortstop instead of Miguel Rojas.


Houston Astros: The Martín Maldonado-Patrick Sandoval Trade

The Deal (July 26, 2018): Houston Astros get C Martín Maldonado (0.1 WAR); Los Angeles Angels get LHP Patrick Sandoval (5.9), international bonus money

Sandoval should probably be a bigger star after pitching to a 2.91 ERA last season. And even though the Astros have a good rotation lined up for 2023, they may find themselves missing the lefty if the guys they have struggle to paper over the absence of reigning American League Cy Young Award winner Justin Verlander.