Top Five worst trades in Pittsburgh Pirates history

Jul 11, 2015; Kansas City, MO, USA; Kansas City Royals pitcher Chris Young (32) delivers a pitch against the Toronto Blue Jays during the first inning at Kauffman Stadium. Mandatory Credit: Peter G. Aiken-USA TODAY Sports

1. December 20, 2002: Chris Young and Jon Searles traded to the Montreal Expos for Matt Herges.

Chris Young never appeared in a game with the Pittsburgh Pirates, but his trade still makes no sense. He was a young prospect with a fantastic arm and appeared to have ridiculously high potential, but out of no where in December of 2002, he was traded for Matt Herges of the Montral Expos. Herges, like Young also never appeared in a game with the Pittsburgh Pirates as three months after the trade, he was given his outright release by the organization.

Chris Young would go on to become a very productive big league pitcher. To date he’s pitched 11 big league seasons and compiled a 73-58 record with a 3.73ERA, a 4.40FIP, an ERA+ of 108 and accumulated 17.3 WAR.

This is one of the most annoying moves of the Littlefield Era. He traded a young, cost controlled starting pitcher for a guy that ended up released three months after the deal. The salt in the wound of this trade is that in 2003 Herges would sign with the San Diego Padres, appear in 40 games with an ERA of 2.86, a FIP of 3.30 an ERA+ of 139. He would then be traded to the Giants and continue his stellar season. Pitching a 2.31ERA, a FIP of 2.66 and an ERA+ of 186 with San Francisco.

Dave Littlefield wasn’t alone in making some bizarre and bad trades, heck even World Series winning management teams can make some boneheaded deals. Which brings us to number three on our list…

Next: Number 3