Jack Entertainment was founded as Rock Gaming in 2009 by seven businessmen led by Dan Gilbert,[1][9] as chairman of its board and Matt Cullen as chief executive officer.

[12][13] In May 2012, Rock Gaming, in a joint venture with Caesars Entertainment, opened Horseshoe Casino Cleveland as well as gained a stake in a Kentucky racetrack, Turfway Park.

[19] Two months later, Jack entered into an agreement to sell the Greektown casino to Vici Properties and Penn National Gaming for a total of $1 billion.

[23] In January 2020, the company also sold the real estate assets associated with its Cleveland casino and the Thistledown racino to Vici in a sale leaseback transaction.

[24] Later in 2020, Gilbert sold his controlling stake in Jack Entertainment to a group of the company's managers, led by chairman Matthew Cullen and CEO Mark Dunkeson.