As a kid, I enjoyed collecting Don Mattingly cards- he was an All-Star and just seemed like a good guy. Once I was old enough to appreciate the connotation of playing for the loathsome Yankees, I kind of wrote him off- he stayed off my sports radar until I got to college. One of my good friends was a huge Mattingly fan, which I found curious since he wasn’t a particularly big baseball fan. When I asked him about it, he painted a persuasive image of Don Mattingly as an endearingly tragic figure.

While Don Mattingly was indeed a great Yankee, he had the misfortune of playing at the worst possible time in the history of baseball’s most successful franchise. The Yankees of the 80’s and early 90’s were a mess, generally overpaid and largely underachieving. Following a loss to the Dodgers in the ‘81 Series (the year before Mattingly broke in), the Yanks wouldn’t make it back to the Fall Classic until 1996- a mere season after Mattingly retired. As such, Donnie Baseball has the dubious honor of being considered the greatest Yankee to have never played in a World Series. Mattingly is also famous for his stance against the late George Steinbrenner’s policy that players maintain well-groomed head and facial hair. Mattingly served a brief team suspension when he refused to cut his mullet, sparking a city-wide controversy that ultimately led to a “loosening” of the rule.

Mattingly played hard and was a clubhouse leader, representing the Yankees well through some of their darkest organizational days- telling “The Boss” to go screw was the icing on the cake. The fact that he never got a shot at a ring seems criminal, even to a Sox fan.