Tampa Bay Devil Rays — 1998

The first season is in the books: 68–94, fifth in a brutal AL East (four teams won 93 or more), 29 games behind Toronto — and five wins better than the real 1998 Devil Rays’ 63–99. Run in commissioner mode with every game auto-simmed, the front office made its calls at the margins: one deadline deal sending Wade Boggs to Toronto, no fire sale, and an extension keeping Fred McGriff in St. Petersburg through 2002. The year closed with three straight wins at Yankee Stadium and a farm system bringing home a long shelf of awards.