6. Sam Cassell – 3 Titles
It’s hard to think of a better way to start an NBA career than by winning two NBA titles right off the bat. That’s like winning an Oscar for Best Actor in your first two movies. That’s exactly what Sam Cassell did after being drafted 24th overall in the 1993 NBA draft by the Houston Rockets.
While he played backup to Kenny Smith throughout his rookie season, he quickly earned the “clutch” label by frequently hitting important shots down the stretch. Cassell’s playoff career was highlighted by his two huge games on the game’s biggest stage, the NBA Finals.
In Game 3 of the 1994 NBA Finals against the New York Knicks, Cassell dropped 15 points, including seven in the final minute to help the Rockets win 93-89. In Game 2 of the following season’s Finals against Orlando, he poured in 31 points off the bench on 4-of-6 shooting from downtown.
While it took him no time at all to become a two-time NBA champion, it took another 13 seasons before Cassell was able to call himself a three-time champ, when he ended up on the Boston Celtics for their 2008 championship run.
5. Gerald Henderson – 3 Titles
Not to be confused with his son, Gerald Henderson Sr. played from 1979-1992, with a tiny stop in Houston shortly before retirement. He was 36 when he joined the Rockets and only played a total of 34 minutes before ending up in Detroit, where he would end his NBA career.
While none of his championship success was with Houston, he still played an important role on two championship-winning Boston Celtics teams in the 1980s.
Henderson averaged 5.8 points per game in the 1981 playoffs to help Boston win it all that year. In 1984, Henderson upped that average to 12.5 points per game through 23 playoff games to win his second ring.
A couple of seasons before briefly joining the Rockets, he won one more title with the Detroit Pistons in 1990, but only played 19 minutes in that postseason.
Next: No. 4 & 3