Number 6: Chris Young
The team that has perpetually needed pitching made a blunder in 2006 trading pitcher and now GM Chris Young to the Padres in 2006. It was a trade that sent Chris Young to play for Bruce Bochy in his last year in San Diego. The Rangers had come up short on trading for Josh Beckett earlier that offseason and overpaid to get Adam Eaton after signing Kevin Millwood. Eaton would leave in free agency after the 2006 season and Otsuka stayed through the 2007 season before departing.
Chris Young would go on to have a long career pitching for the Padres, Mets, Mariners, and Royals. He won a World Series in Kansas City in 2015. He was never a great pitcher, but he would have fit in nicely on those World Series teams as a 3rd or 4th starter. The one good thing about that trade was that Young spent one season pitching for Bruce Bochy and developed a relationship that led him to hire Bochy as Rangers manager 17 years later.