dan gilbert casino Tony Dejak/AP
Dan Gilbert, left, celebrates with gaming executives on Nov. 4, 2009, after Cleveland voted to legalize casino gambling.
  • Cleveland Cavaliers owner Dan Gilbert is the billionaire founder of Quicken Loans and oversees more than 100 companies, including the Jack Entertainment casino group.
  • Gilbert is based in Detroit, but in 2009 he was a pivotal champion of legalizing casino gambling in Ohio so that he could expand his business.
  • The episode shows how Gilbert has built his empire by transforming communities rather than just building in them.

When Dan Gilbert expands his businesses, he doesn’t move to a place and stand idly by. Since moving his mortgage company Quicken Loans’ headquarters to Detroit in 2010, he’s invested more than $3.5 billion (with $2.1 billion more in development) into the city’s downtown, where his company Bedrock owns about 60 properties. And before that, after he became the majority owner of the Cleveland Cavaliers NBA team in 2005, he began thinking of ways to expand his influence there, as well.

“There’s a natural…