The Worst Trades The Pirates Have Ever Made

The Pittsburgh Pirates have been around so long that they predate Major League Baseball itself. Their first official season as a franchise was in 1882 as Allegheny City. They joined the National League in 1887 and moved to Pittsburgh in 1891.

The Pirates won their first World Series in 1909 – and their most recent in 1979. In that span, they've made a lot of trades, either to get better or, in modern times, to release salary and build for a better future.

Some trades have worked, some have not.

Here are the four worst trades in Pittsburgh Pirates history.

4. Aramis Ramirez and Kenny Lofton to Cubs for Jose Hernandez, Bobby Hill and Matt Bruback (2003)

It was a salary-dump move at a low point, but it didn't have the desired effect.

Related: Dodgers Worst Trades In Team History

The veteran infielder Hernandez played 48 games for Pittsburgh, batting .223 before moving on to the Dodgers in 2004 (and hitting .289). Hill hit two home runs and didn't steal a base in 184 games in Pittsburgh before his pro career ended. Bruback spent nine seasons in the minors before retiring.

Meanwhile, Ramirez went on to become a beloved third baseman for the Cubs and later the Brewers, making three All-Star appearances and finishing with 386 home runs.

Loften finished out 2003 in Chicago and batted .327, then played four more seasons, batting .301 and annually stealing 20-plus bases the rest of his career.

3. Robinzon Diaz to the Blue Jays for Jose Bautista (2008)

Bautista was a three-year starting third baseman for the Pirates who was hitting 15-16 home runs per year, driving in 50-60 RBI. But he was being squeezed when the team acquired Andy LaRoche in a trade. So he moved Bautista to the Jays for the dreaded "player to be named later."

That player, the catcher Diaz, played 43 games over two seasons for the Pirates before calling it a career.

Bautista, meanwhile, became a primary outfielder in Toronto. He also became a six-time All-Star, had seasons with 53 and 47 home runs, led the league in walks on two occasions, and four times finished Top 8 in AL MVP voting.

2. Preacher Roe, Billy Cox and Gene Mauch to the Dodgers for Dixie Walker, Hal Gregg and Vic Lombardi (1947)

Walker was the gem for the Pirates in the deal. He was a four-time All-Star in Brooklyn, including his last two campaigns at ages 35 and 36. But in Pittsburgh, his production cratered. He managed 54 RBI in 129 games for the Pirates in 1948, averaging 111 in the three previous seasons. He hit 19 doubles (34 average L3 years) and scored only 39 runs (86.3).

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The LHP Lombardi was a solid starter-reliever in three seasons with the Dodgers (3.07 ERA in 112 games) but fell apart in three seasons after the move (4.60 ERA in 111 games). The RHP Gregg didn't do much.

Meanwhile, Roe was a star for the Brooklyn Dodgers, receiving MVP votes as a pitcher four straight years, all All-Star campaigns.

In 1951, he went 22-3 with a 3.04 ERA. Cox was a standout infielder who played on four World Series teams in Brooklyn, including the 1955 champion.

1. Tyler Glasnow, Austin Meadows, Shane Baz to the Rays for Chris Archer (2018)

This one hurts both in what was gained and what was lost.

Archer was considered a great prospect in the early 2010s, but hadn't panned out. He was the Rays' two-time All-Star, but with an ERA that hovered around 4.00. Still, the Pirates went big to acquire him. Archer was 3-5 with a 4.31 ERA with the Rays when the Pirates acquired him, and 3-3 with a 4.30 ERA after the swap.

Archer lasted just one more season in Pittsburgh, going 3-9 with a 5.19 ERA in 2019. He played more seasons elsewhere before retiring.

More pain comes with what was sent off.

Glasnow had injury issues in Tampa but was 6-1 with a 1.78 ERA in 2019, 5-1/4.08 in '20 and 5-2/2.66 in '21. He is still going strong as a starter for the two-time World Series champion Los Angeles Dodgers.

Meadows was an All-Star in his first full season in Tampa, with 33 home runs and a .291 average. He finished in the Top 20 in MVP voting twice before he went to Detroit in 2022, and his career fizzled. Baz was a reliable starter for two seasons in Tampa and is now with the Orioles.

Related: The Worst Trades The Braves Have Ever Made

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This story was originally published June 25, 2026 at 6:18 PM.