9. Houston Texans, NFL – $700 million by Bob McNair in 2002
After Houston Oilers owner Bud Adams moved the team from the Astrodome to Tennessee in 1996, the NFL to bring a football team back to Houston and awarded the ownership of the new team to Bob McNair, a billionaire with strong ties to the city of Houston.
But winning didn’t come easily for the Texans, who started their existence with five straight losing seasons. But the team finally got over the hump in 2011 and made the playoffs in two straight seasons.
8. Chicago Cubs, MLB – $700 million by Thomas S. Ricketts in 2009
Arguably the most star-crossed franchise in the sporting world, the Cubs have not won a World Series since 1908 and have not made an appearance in the MLB title series since 1945. But that didn’t stop former Incapital LLC CEO Thomas S. Ricketts from making the winning bid for the team in 2009 – and it didn’t stop the Cubs from losing either.
Since Rickets took over, the Cubs have failed to make the playoffs every season and have just one winning season.