Year: 1994

Dave Winfield is a Hall of Famer, but that doesn't mean he is immune from the weird world of baseball trades. His involvement came at the very end of his career, when the Twins were looking to part with their 40-year-old outfielder during the 1994 players' strike. They struck a deal with the Indians to swap Winfield for a player to be named later, but when the season was canceled, the teams were stuck. To ensure the trade went through, the Twins' executives took their Cleveland counterparts out for dinner and paid the tab, effectively trading Winfield for some steaks masquerading as "cash."