2 Pirates trade steals continue to haunt elite MLB franchises

The Pirates have had their fair share of awful trades in the past couple of decades. Whether it was Neal Huntington's generally awful Chris Archer trade or some of the regularly bad trades made by Ben Cherington, such as the Josh Bell and Starling Marte trades, Bucs fans are used to being haunted by trades.

Although these trades have all been at the Pirates' expense, even a broken clock is right twice a day. Joel Reuter of Bleacher Report recently wrote an article about 20 MLB trade deadline deals that haunt teams, and the Pirates made the list twice, for positive reasons.

2 Pirates trades that haunt the opposing teams - congrats, Ben Cherington!

The Oneil Cruz Trade

The Oneil Cruz trade was one that looked good for the Pirates even before Cruz entered the Major Leagues. In 2017, Oneil Cruz was traded from the Dodgers' farm system at 18 years old for long-time Pirates reliever Tony Watson.

Watson was solid with the Dodgers for the remainder of that 2017 season, posting a 2.70 ERA, but those 20 innings he pitched after the trade deadline were the only innings he ever pitched for the Dodgers.

Cruz was the Dodgers' 17th-best prospect at the time and was looked at as a shot in the dark for the Pirates. Neal Huntington, the former Pirates GM who made this trade, didn't last long enough to reap the benefits, but he gave Pirates fans something to be happy about on the way out.

Of course, now, Cruz is the best hitter on the Pirates' active roster, with 12 home runs and an .828 OPS. The proposition of adding another power bat to the Dodgers' lineup is scary, and the league better thank Neal Huntington for getting Cruz out of that Dodgers farm system back in 2017.

The Bailey Falter Trade

Quite possibly the most random trade of the year at the time has become impactful in a short period of time. Falter was having a horrible year for the Phillies in 2023 and was traded to the Pirates for infielder Rodolfo Castro, who is infamous for his phone falling out of his pocket in a game.

Castro was hitting just .228 at the time for the Pirates, so neither player in this trade had any real value. Castro went on to play just 14 games for Philadelphia in 2023 and had just three hits in 32 plate appearances. Since 2023, Castro has bounced around the Phillies' farm system.

Normally, a trade like this would go down as a wash with two teams taking chances on underperforming players, but that did not end up being the case. Falter has been great for the Pirates. After a bad 2023, Falter was solid in 2024, pitching 142 innings at the back end of the Bucs' rotation.

Falter's 2025 is what landed him on this list. Falter has been dominant in 2025, holding an ERA of 3.14. In May, he broke the record for the lowest ERA in one month in Pirates history (with at least six starts) at 0.76. Adding a top-25 WHIP, Falter has been one of the best pitchers in the NL.

The Phillies have multiple great starting pitchers, but with Aaron Nola's rough start and injury concerns, the Phillies front office has to be kicking themselves for letting go of Falter for virtually nothing. Ben Cherington hasn't done much right in his tenure, but this was a fleece for the Pirates' GM.