My thought process was to find great — in some cases Hall of Fame — players that had a short stint with the Yankees well past their prime. It was pretty easy to fill the lineup just by scrolling through a decade of rosters from the mid 2000s on, until I got to shortstop (thanks, Derek). I also tried to construct a good, well-rounded, lineup, and I think I achieved that.
This lineup has lefty-righty balance, a great lead-off man in Lofton, power in the middle with AJ and Canseco, and good contact guys like Olerud so we’re not an all-or-nothing team.