Bobby Abreu for Kevin Stocker
This one is an easy call as the most unfortunate trade in franchise history. Sure, at the time of the deal, nobody knew Bobby Abreu would go on to become a possible Hall of Fame player. Now that we have the luxury of looking back on this deal through the spectacles of hindsight, which provide you with 20/20 vision, it’s not good.
This was another expansion draft trade.
With the third pick of the first round and sixth overall pick, the Rays selected Bobby Abreu. He was only 23 with a career OPS+ of 84 at the time of his selection. Abreu was obviously a talented player but the Rays were focused on getting a good defensive shortstop to anchor the infield, and to also make sure they had someone to play shortstop.
They quickly traded Abreu to the Phillies for Kevin Stocker. Stocker would hit just .208 in his first season (OPS+ of 54) with the Rays and .299 the following year. The light-hitting shortstop would find himself out of the game following the 2000 season.
Meanwhile, Abreu made an immediate impact for the Phillies in 1998 slashing .312/.409/.497 with 29 doubles, six triples, 17 homers, 19 steals, and 84 walks. Abreu would complete an 18-year career in which he smashed 574 doubles, 288 homers, and slashed .291/.395/.475 over 2,425 games.
Had the Rays not have made those expansion draft trades, 1998 could have been a lot more fun. Imagine a lineup that mixed the two breakout seasons of youngsters like Dmitri Young and Bobby Abreu with the veteran bats of Wade Boggs and Fred McGriff.