He became president of the New York Knicks in March 1991, and in his four seasons as president, the team made it to the Eastern Conference Finals three times and went to the NBA Finals in 1994 and 1999. The team set records for attendance, television ratings and revenue under his watch.
He went on to become president and chief executive officer of Madison Square Garden, the company that owns the New York Rangers, New York Knicks, New York Liberty of the WNBA and Madison Square Garden and the MSG television network. In 1997, MSG acquired Radio City Music Hall. From 1997 to 2001, the Rangers failed to make the playoffs four straight seasons despite having one of the highest payrolls in the NHL.
In September 2001, Checketts founded Sports Capital Partners Worldwide, a consulting and investment service firm for sports teams. In 2002, SCP acquired SportsWest Communications, a syndicated broadcaster of college sports. In July 2004 SCP bought into Major League Soccer and established a team in Utah, Real Salt Lake, which began play in April of 2005.
Checketts attended the University of Utah and got a master's degree in business administration from Brigham Young University. After graduation, he joined the Boston-based consulting firm of Bain & Company.
Checketts is a member of The Church of Jesus Christ of Latter-day Saints. He was also featured in a book titled The Mormon Way of Doing Business.