Hamilton played 14 seasons in the National Basketball Association (NBA) and is best known for his nine-year stint with the Detroit Pistons, where he was a three-time All-Star.

Born and raised in Coatesville, Pennsylvania, a city 40 miles (64 km) west of Philadelphia, Hamilton played three years for the University of Connecticut.

Named a consensus first-team All-American, Hamilton decided to forgo his senior year and enter the NBA draft.

Drafted seventh overall by the Washington Wizards where he would spend the next three seasons, Hamilton notably averaged 20 points per game starting next to Michael Jordan.

He was named the 1999 NCAA tournament's Most Outstanding Player after UConn's run to that year's national title after averaging 24.2 points per game.

Number 1 UConn's race to the top also included a close, physical defeat of the national Cinderella team no.

The Huskies were nine-point underdogs, but upset the Blue Devils after Hamilton contributed 27 points, 7 rebounds, and 3 assists in the final game.

In his first career game, Hamilton recorded 10 points in almost 16 minutes of playing time on a 94–87 win over the visiting Atlanta Hawks.

In the off-season, Michael Jordan announced that he would return to the court for the Wizards, and Doug Collins was hired to coach the team.

With Jordan now the team's small forward, Hamilton moved back to shooting guard and assumed the starting role.

In September, the Wizards traded Hamilton to the Detroit Pistons, along with Bobby Simmons and Hubert Davis, in exchange for Ratko Varda, Brian Cardinal, and All-Star scorer Jerry Stackhouse.

In a back-and-forth seven-game series against the Nets, Hamilton scored 21 points and grabbed 6 rebounds in the decisive Game 7 victory, as the Pistons came back from a 3–2 deficit.

[15] The Pistons were viewed as a major underdog in the Finals, as they faced the star-studded Los Angeles Lakers, who were just one season removed from winning three straight championships.

Adding a new chapter to the Lakers–Pistons rivalry of the late 1980s and early 1990s, the Pistons dominated game 1 in Los Angeles and shocked the Lakers 87–75.

In a match-up overshadowed by the brawl between the two teams earlier in the season, the champs overcame a 2–1 series deficit with Hamilton scoring 28 points in the decisive game six victory.

Detroit faced the San Antonio Spurs in the Finals, led by all-stars such as Tim Duncan, Tony Parker, and Manu Ginóbili.

He also led the league in three-point field goal percentage with .458, as the Pistons excelled throughout the season and won a franchise-record 64 games.

This set up a rematch with Miami, and while the Pistons had home court advantage they had no answer for the dominant play of Dwyane Wade, and lost in six games.

The Pistons won 53 games, and swept the Orlando Magic in the first round of the playoffs before defeating Chicago and Wallace in the conference semifinals.

[20] Detroit advanced to their sixth straight appearance in the Eastern Conference Finals, but fell to the Boston Celtics in six games.

[21] Indeed, changes began immediately when Flip Saunders was dismissed as head coach, despite the best winning percentage in Pistons history.

Just two games into the 2008–09 season, Detroit traded Hamilton's longtime backcourt mate Chauncey Billups in exchange for former MVP Allen Iverson.

[31] Hamilton cleared waivers on December 14, 2011, and quickly signed a three-year, $15 million contract with the Chicago Bulls, with the third year being a team option.

On November 26, 2012, Hamilton scored a season-high 30 points, but missed a shot as time expired that would have won the game, in a 93–92 loss to the Milwaukee Bucks.

Special guests included Dwyane Wade, Rasheed Wallace, Chauncey Billups, Michael Jordan, and many others.