

James later stated, "I've met with Dan, face-to-face, man-to-man. Gilbert later claimed that he regretted the letter, and has since apologized to James. Gilbert was later fined by NBA Commissioner David Stern for his remarks. Following the special, Gilbert published an open letter to Cleveland Cavaliers fans in which he criticized how James made his announcement. In July 2010, Ohio native LeBron James announced that he was leaving the Cavaliers for the Miami Heat on an ESPN television special dubbed The Decision. In 2011, Gilbert purchased the New Mexico Thunderbirds from what was then the NBA Developmental League (now called the G League), and moved them to Canton, Ohio renaming them the Canton Charge, and making them the Cavaliers' affiliate. In 2016, the Monsters won the AHL's top prize – the Calder Cup – giving Gilbert two championships within eight days. In 2007, Gilbert bought the dormant Utah Grizzlies American Hockey League franchise, moved it to Cleveland and renamed it the Lake Erie Monsters (now Cleveland Monsters). During Gilbert's tenure, the Cavs won six Central Division championships (2009, 2010, 2015, 2016, 2017, 2018), five Eastern Conference championships (2007, 2015, 2016, 2017, 2018), and one NBA championship (2016), which ended the 52-year Cleveland sports curse. Gilbert became majority owner of the Cleveland Cavaliers in March 2005 and undertook a complete overhaul of the front office, coaching staff, player personnel and game presentation. In August 2020, Quicken Loans went public under the name Rocket Companies and made its debut on the New York Stock Exchange under the ticker symbol “RKT.” As of 2020, Gilbert remained the majority owner, controlling 79% of the company's shares.

All 3,600 Michigan-based employees moved into Detroit's urban core by the end of 2010. In 2007, Gilbert and the city of Detroit announced an agreement to move the company's headquarters to downtown Detroit.

As of 2021, Gilbert served as the chairman of Quicken Loans, Inc. In 2002, Gilbert and a group of private investors purchased Quicken Loans and its affiliated national title company, Title Source, Inc., from Intuit. purchased Rock Financial and renamed the national web operation Quicken Loans. In the fourth quarter of 2017, the company became the largest retail mortgage lender by volume in the United States. In the late 1990s, the company launched its internet strategy, becoming an early online direct mortgage lender. Gilbert founded Rock Financial in 1985 with his younger brother Gary Gilbert.
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While in college he earned a real estate agent's license and while in law school, he worked part-time at his parents' Century 21 Real Estate agency. He earned his bachelor's degree from Michigan State University and a Juris Doctor from Wayne State University Law School, and is a member of the State Bar of Michigan. He grew up in Southfield, Michigan, where he attended Southfield-Lathrup High School. Gilbert was born to a Jewish family in Detroit, Michigan.
