In 2013, PGA Tour professional, Brian Gay, offered to lend his name to the inaugural Diamond Resorts-sponsored golf invitational in an effort to help raise money for Florida Hospital for Children.

[8] In its second year, the Diamond Resorts Invitational was held at Isleworth Country Club in Windermere, Florida from December 11–14, 2014.

More than 400 people participated in the weekend event, which included a celebrity/amateur golf tournament and private concert by country music artist Colt Ford.

It was held January 12–17, 2016 at The Golden Bear Club in Windermere, Florida and featured a Stableford scoring format with a $500,000 purse.

[10] The celebrity lineup included Super Bowl MVPs Jerry Rice, Marcus Allen, Richard Dent and Mark Rypien; Atlanta Braves Hall of Fame pitcher of Greg Maddux, John Smoltz and Tom Glavine; ESPN college football expert and former NFL quarterback Danny Kanell; baseball legends Reggie Jackson, Roger Clemens and Gaylord Perry; and celebrity entertainers Larry The Cable Guy, Jake Owen and Colt Ford.

The players were organized into threesomes of one professional and two celebrities, and competed side-by-side in a Modified Stableford scoring format for separate purses totaling $1.25 million.