8. The Cape Cod Buccaneers
In 1979, before he was a billionaire (or even owner of World Wrestling Entertainment), Vince McMahon struck a deal to lease the Cape Cod Coliseum in his then-home of Cape Cod, Massachusetts. He brought a number of different acts from all walks of entertainment to the arena, and actually managed to promote events there more successfully than his predecessors. After a very lucrative preseason hockey game between the Buffalo Sabres and the Boston Bruins, Vince saw an opportunity. In 1981, he purchased the rights to the Cape Cod Buccaneers, a franchise in the newly-formed minor-league Atlantic Coast Hockey League (ACHL). McMahon scouted coaches and players, and the team (and the league) started operations off in October 1981. Unfortunately, though, the success of the NHL game didn't carry over as the area was so sparsely populated, McMahon had trouble keeping his arena filled for games. Compounding the lack of fan support was the fact that the Buccaneers weren't very good, compiling a record of 17-21-1 in their first (and only) seaason. On February 1, 1982, Vince McMahon folded the Cape Cod Buccaneers, the strain on his finances simply having become too great. He would soon move to Greenwich, Connecticut, and take more of an active role in WWE, buying the promotion from his father before the end of the year. The ACHL as a whole would fold in 1987, becoming as much of a memory as Vince McMahon's foray into professional hockey.
Final Tally: $30,000 loss