The year is 2002. The Boston Red Sox have a vacant General Manager position that they want to fill. And who did they consider as the man to ultimately build a curse-ending team?
Yes, according to this recently-unearthed 2002 article from the Pittsburgh Post Gazette, the then-newly-hired Littlefield was considered by the Red Sox as a possible candidate for their vacant job. Fortunately for them, Littlefield was under contract to the Buccos for years and years to come, and as the article points out, "The Red Sox, however, have not contacted the Pirates for permission to interview Littlefield, and permission likely would be denied if they did".
As we all know, the Sox hired 28-year-old Theo Epstein in November of '02, and by 2004 the Sox were hoisting a World Series trophy over their heads.
And Littlefield? He's now employed as a scout with the Chicago Cubs after driving the Pirates further into the ground during his years in Pittsburgh.
Isn't history fun?
Littlefield not talking to Boston [PG, Wednesday, October 23, 2002]