1. Dec. 9, 1982: Yankees Trade Future Hall of Famer Fred McGriff, Mike Morgan to Toronto for 2 People Named Dale Murray, Tom Dodd
Now that Fred McGriff is officially a Hall of Famer, this trade goes from "One of the Worst Ever" to "Definitively the Yankees' Worst Ever."
The Bombers drafted McGriff and uncovered his talent in the ninth round back in 1981, which makes the whole thing that much worse. Ultimately, he spent two years in the Yankees' system, hitting .148 in 29 games of Rookie Ball as a 17-year-old in 1981, then hitting .272 and bashing 9 homers in 62 games while repeating the level the next year. Instant progress!
But ... that was it. McGriff, as well as future journeyman and 141-game winner Mike Morgan, were shipped impatiently to the Blue Jays after the season for very little gain. Murray put up a 4.48 ERA in relief in '83 and a 4.94 mark in '84. Dodd played in eight MLB games in 1986, but never appeared for the Yankees again (we call that ratio The Frankie Montas).
McGriff? He didn't debut in the bigs until 1986 either and didn't break out until 1988, too long a wait for the impatient Yankees. They could've probably used his 34 bombs as a 24-year-old that season, though, especially considering his power bat arrived at the exact same time Don Mattingly began to break down. A potential Mattingly/McGriff DH rotation through the mid-90s sounds like a pleasant outcome, but the Yankees pulled the plug on their teenage draft pick far too soon. As per usual.