He has won five NBA championships as a head coach, four with the Los Angeles Lakers during their Showtime era in the 1980s and one with the Heat in 2006.

He is the son of Mary Rosalia (Balloga)[4][5] and Leon Riley, who played 22 seasons of minor league baseball as an outfielder and first baseman, and appeared in four games for the 1944 Philadelphia Phillies.

[6][7] Riley played basketball for Linton High School in Schenectady under head coach Walt Przybylo and assistants Bill Rapavy and Ed Catino.

Coached by Adolph Rupp, UK lost to Texas Western (today's UTEP), a game that was reenacted in the movie Glory Road.

[22] With rookie guard Magic Johnson and longtime star Kareem Abdul-Jabbar, the Lakers defeated the Philadelphia 76ers in six games in the 1980 NBA Finals, giving Westhead and Riley championship rings in their first year coaching the team.

Riley ushered in the Lakers' "Showtime" era, along with superstar players Johnson and Abdul-Jabbar with their running game.

Riley became a celebrity in his own right, a fashion icon for his Armani suits and slicked-back hair which complemented the team's Hollywood image.

[25] Besides using Lakers' up-tempo style established by McKinney and Westhead, Riley was also innovative on defense; he was one of the first coaches to employ a 1-3-1 half-court trap to pick up the pace of the game.

Both teams returned to the Finals the next year, and this time Riley's Lakers, hobbled by injuries to Norm Nixon, Bob McAdoo and rookie James Worthy, were swept by the 76ers.

With future Hall of Famers Magic Johnson, James Worthy and Kareem Abdul-Jabbar, plus Byron Scott, A.C. Green, Mychal Thompson, Kurt Rambis, and Cooper, the Lakers finished 65–17 in the regular season, third-best in team history.

They met with similar success in the playoffs, dispatching the Celtics in six games to win Riley his third NBA title.

The Lakers beat the Detroit Pistons in seven games in the 1988 NBA Finals, making good on Riley's promise.

In the days leading up to the 1989 NBA Finals, Riley took his team to a mini-training camp in Santa Barbara, California in hopes of keeping his players in peak physical form.

[33] After stepping down, Riley accepted a job as a television commentator for NBC for one year before being named head coach of the New York Knicks, starting with the 1991–92 season.

Commentators admired Riley's ability to work with the physical, deliberate Knicks, adapting his "Showtime" style with the fast-paced Laker teams in the 1980s.

[34] Riley returned to the NBA Finals, in 1994, en route to defeating the three-time defending champion Bulls (without Michael Jordan) in seven games during the Eastern Conference semifinals.

However, he had the unfortunate distinction of becoming the first (and to date, only) coach to lose an NBA Finals Game 7 with two teams, having lost to the Celtics, in 1984.

In 1995, Riley resigned from the Knicks via fax to become president and head coach of the Miami Heat, with complete control over basketball operations.

This Heat season was notable for personnel changes, as the team welcomed franchise building blocks Alonzo Mourning and Tim Hardaway.

Advancing to the Eastern Conference finals for the first time in franchise history, the Heat were again defeated by the eventual champion Bulls.

Riley was selected as Coach of the Year for the third time after leading Miami to a 61–21 regular season record and first place in the Atlantic Division.

The Heat then lost two of their best players when guard Tim Hardaway was traded to the Dallas Mavericks and Anthony Mason signed with the Milwaukee Bucks.

After the Heat finished the 2002–03 season 25–57, Riley stepped down as head coach and was succeeded by longtime assistant Stan Van Gundy.

In July 2004, Riley traded Caron Butler, Brian Grant, Lamar Odom, and a first-round draft pick to the Lakers for star center Shaquille O'Neal.

Wade and O'Neal led the Heat to the Eastern Conference finals during the 2005 playoffs, where they lost to the defending champions Detroit Pistons after leading the series 3–2.

[40] During the 2005 off-season, it was widely speculated that Riley was attempting to push Van Gundy out and make himself head coach once again now that the team was a championship contender.

The team had lost several of its players to extended injuries, and a disgruntled Shaquille O'Neal was traded mid-season.

[47][48] In 2010, Riley acquired LeBron James and Chris Bosh to form the Heat's "Big Three" with Dwyane Wade.

Before the season, Riley traded for Jimmy Butler, drafted Tyler Herro, and signed the undrafted Kendrick Nunn.

One of the phrases Riley coined in the book was the "Disease of More", stating that "success is often the first step toward disaster" and that defending champions often fail the following season because every player who returns wants more playing time, more shots per game, and more money.