The tournament had its roots in a game that is considered one of the greatest upsets in college history. On December 23, 1982 the top-ranked and undefeated University of Virginia made a scheduled trip to Honolulu for a game. Originally seeking to play the University of Hawaii, Virginia agreed to play Chaminade, which at the time belonged to the NAIA, on the trip instead. In a game that was not televised and only covered by one sportswriter from outside the local media, Chaminade defeated the Ralph Sampson-led Virginia squad 77–72 in front of 3,300 spectators at the Neal S. Blaisdell Center. Shortly after the upset, Virginia head coachTerry Holland congratulated Chaminade's athletic director, Mike Vasconcellos, and suggested to him that he consider beginning a Hawaii tournament. Two years later, the Maui Classic was inaugurated with Chaminade reaching the finals and losing to Providence. Today the tournament provides schools an opportunity to compete on a neutral court with some of the top basketball programs in the country. Associated Presscollege basketball editor Jim O'Connell called the Maui Invitational "the best in-season tournament in the country – the standard by which all others are compared." Some 108 schools representing 26 conferences and 40 states have competed in the Invitational. Five times the winner has gone on to win the NCAA Men's Division I Basketball Championship later that season: Michigan in 1988, North Carolina three times—in 2004, 2008, and 2016, and UConn in 2010. Of the eight teams which play in the tournament, generally there is one from each of the six major conferences, one from another conference such as the American Athletic Conference, Conference USA, the Mountain West Conference or the Atlantic 10, and Chaminade. Beginning with the 2011 tournament, the field includes four additional mainland teams that play the Maui-bound teams at home. The four mainland teams will then play each other in regional games. The winner from each game will square off in the championship contest, preceded by the consolation game between the losers. Beginning in 2018 and continuing with every even-numbered year, Chaminade will play games on the mainland, and eight Division I schools will compete in the championship bracket on Maui. In odd-numbered years, Chaminade will compete in the championship bracket.
Each year more than 4,000 out-of-state visitors—boosters, players, officials, team and game personnel, media representatives, sponsors, production crews and basketball fans—attend. The 2007 Maui Invitational Tournament ranked among Hawaii's top revenue-generating events, bolstering the local economy by more than $8 million according to financial data released by the Maui Visitors Bureau. The tournament has brought more than $110 million to Maui's economy since the tournament's debut in 1984.
