Purchase price (year): $8.5 million (1982)
Current team value: $1.03 billion
Stanley Cups as owner: 4 (1997, 1998, 2002, 2008)
Bottom line: Former minor league baseball player Mike Ilitch and his wife, Marian, opened the first Little Caesars pizza restaurant in 1959 outside of Detroit — it would be the building block for a multibillion-dollar fortune.
The Ilitchs purchased the NHL’s Detroit Red Wings in 1982 and the MLB’s Detroit Tigers in 1992, paying just under $90 million for the two teams, which are worth a combined $2.5 billion in 2023. Both teams have won championships since, with the Red Wings winning four Stanley Cups in 1997, 1998, 2002 and 2008.
The Iltich’s youngest son, Christopher, has been the CEO of the Red Wings, Tigers and Little Caesars since 2010. They’re one of the most respected ownership groups in all of professional sports.