Michael Flaskey


Michael A. Flaskey, known as Michael Flaskey, is an American businessman and chief executive officer of the timeshare company Diamond Resorts. He is also the founder and executive director of the Diamond Resorts Invitational and the Diamond Resorts Tournament of Champions™, held annually in Orlando, Florida.

Personal life

Flaskey attended Limestone University, previously known as Limestone College, where he was one of the first five players to sign with the Limestone baseball program under Hall of Famer Gaylord Perry and was named to the NAIA All-District team. He graduated in 1992 with a bachelor's degree in physical education. In 2009, he was inducted into the Limestone Athletics Hall of Fame.

Business activity

In March 2017, Flaskey was named chief executive officer of Diamond Resorts International. Prior to joining Diamond Resorts, Flaskey held senior leadership positions with Starwood Vacation Ownership from October 2003 to July 2006 and with Fairfield Resorts from August 1992 to September 2003. He serves on the board of directors of Soberlink, Inc. He is also on the board of directors for Diamond Resorts.
At Diamond Resorts, Flaskey launched Events of a Lifetime, an experiential vacation platform. He also is the founder of the Diamond Resorts Invitational, a mixed event celebrity golf tournament held annually in Orlando, Florida. In 2019, the tournament transformed into the Diamond Resorts Tournament of Champions™, an official LPGA event featuring LPGA winners from the previous two seasons playing alongside a roster of world-class sports and entertainment celebrities.
Flaskey regularly appears on the MLB Network and has appeared several times on Golf Channel with professional golfers and celebrities, including John Daly and Lee Janzen.

Charitable activity

Since 2013, Flaskey has helped manage the Diamond Resorts Invitational to raise more than $4.1 million for Florida Hospital for Children.