Lester was a member of the 1979 USA Basketball team that won the gold medal in the 1979 Pan-American Games.

After 24 years in the Lakers organization, with seven NBA titles, Lester served as a scout for the Phoenix Suns from 2011 to 2015.

Born in Canton, Mississippi, Lester grew up in a public housing project in Chicago, Illinois.

Growing up in the Stateway Gardens housing project near Comiskey Park in Chicago, Lester was raised by his single mother Nadine, along with his with three sisters.

[1] Lester started on the varsity team at Dunbar High School of the Chicago Public League as a 5'6" sophomore.

[2] As a senior, Lester averaged 27.0 points per game, playing alongside teammate Ken Dancy, who was a future 1980 NBA draft pick.

[2] Lester led the Dunbar Mighty Men to the Chicago Public League Championship playoffs, where they lost 75–60 to Morgan Park High School, with University of Illinois recruit Levi Cobb.

Lester ultimately chose Iowa after being recruited by Arizona, Creighton, Louisville, Nebraska and Texas-El Paso.

"[6] Every Friday after practice in Iowa City, Olson, accompanied sometimes by his wife Bobbi, would drive to Chicago to visit Lester.

"He lived in an area that probably not a lot of people wanted to go into and visit with him and his mom," Olson said in 2015, recalling his recruiting of Lester.

[7][8] Starting for Iowa as a freshman, Lester made an immediate impact, averaging 13.4 points, 3.6 assists and 2.4 rebounds in 1976–1977.

Iowa finished 18–9, as Lester was second on the team in scoring, behind Bruce "Sky" King's 21.0 points, and he led the Hawkeyes in assists.

[12] Lester represented the US as a member of the 1979 Team USA that went 9–0 and won the gold medal in the Pan-American Games.

The roster included Hall of Famers in Isiah Thomas, Kevin McHale and Ralph Sampson, as well as Mike Woodson, Kyle Macy, Ray Tolbert, Danny Vranes and Michael Brooks.

[19][20][21] Lester's knee improved and he returned for the end of the regular season, with Iowa having lost three of its previous four games.

Iowa had been so decimated by injures, the team, which relied mostly on six players in Lester's absence, was labeled the "Fabulous Few."

[22][18][20] With an 18–8 record, Iowa received an at–large bid and a #5 seed in the East Regional of the 48–team 1980 NCAA Division I Basketball Tournament.

[23] Lester then had 17 points and four assists in just 28 minutes, as Iowa defeated North Carolina State and coach Norm Sloan 77–64 in the sweet sixteen.

[24] In the elite eight, Iowa faced #1 seed Syracuse under coach Jim Boeheim, with Louis Orr and Danny Schayes.

Lester had eight points and nine assists, taking just seven shots, with his playmaking and distribution helping Iowa to shoot 31 of 51 (60.8%) for the game, along with making 19 of 20 free throws.

[20][18][26][27] In the NCAA National Semi–Final, Lester injured his knee 12 minutes into the game, after scoring 10 of Iowa's first 12 points on 4 for 4 shooting and 2 for 2 from the line.

"[29] “It was frustrating getting hurt from the beginning and missing half my senior year,” Lester said of the Final Four season.

But we had great team success and that’s what it’s about, winning and losing as a team.”[30] Even after the continued success Lute Olson enjoyed at the University of Arizona (including four Final Four appearances, a National Championship, with players such as Mike Bibby, Gilbert Arenas, and Jason Terry), Olson regards Lester as the best player he ever coached.

Hall of Famer Earvin "Magic" Johnson, who played at Michigan State University, once called Lester the toughest opponent he ever faced in the Big Ten.

In the Eastern Conference playoffs, the Bulls defeated the New York Knicks, 2–0, before losing to the eventual 1981 NBA Champion Boston Celtics, 4–0.

Lester would spend the next 24 seasons with the Lakers organization in various capacities, being a part of seven NBA Championships: one as a player, three as a scout, and three as assistant general manager.

[34][42] In 1984–1985, serving as the backup to Magic Johnson, whom he had played against at Michigan State, Lester averaged 2.8 points and 2.5 assists in 32 games as the Lakers won the NBA Championship.

He requested that the training room in Carver-Hawkeye Arena be named after longtime (1972–2012) Iowa athletic trainer John Streif.

"[31] Over time, Lester, Lute Olson, his Iowa teammates and fans contributed to help Kenny Arnold.

Teammates Lester and Mike "Tree" Henry accompanied Arnold on the successful hospital visit.