In 1998, after Shaw became disgruntled with his role with the Warriors, he was traded alongside Joe Smith to the Philadelphia 76ers for Jim Jackson and Clarence Weatherspoon.

During the 1999 offseason, the Blazers resigned Shaw to be traded alongside Ed Gray, Walt Williams, Carlos Rogers, Stacey Augmon, and Kelvin Cato to the Houston Rockets for Scottie Pippen.

He served as a backup to All-Star shooting guard Kobe Bryant throughout the season and playoffs as the Lakers had the league's best record winning 67 games.

Shaw played in all 22 of the Lakers' playoff games as they advanced past the Sacramento Kings and the Phoenix Suns before facing the Portland Trail Blazers in the Western Conference Finals.

While a member of the Heat, on April 8, 1993, Shaw hit a then-NBA record ten three-point field goals (out of 15 attempts) against the Milwaukee Bucks at the Bradley Center, finishing with 32 points.

During his first stint with the Lakers, he worked with legends Kobe Bryant, Shaquille O'Neal, Karl Malone, Pau Gasol, Gary Payton, Lamar Odom, while the team won the 2009 and 2010 NBA Finals but came up short in 2004 and 2008.

He was considered for the Lakers head coaching job following Phil Jackson's retirement, but was ultimately passed over in favor of Mike Brown.

He was later promoted to associate head coach in 2012–13 season where the team lost game seven in the Eastern Conference Finals against the Miami Heat Big Three.

The team experienced success under Shaw with a new core of Paul George, David West, Danny Granger, and Roy Hibbert.

[11] He notably coached rookie Nikola Jokić as well as Andre Miller, Evan Fournier, Ty Lawson, Arron Afflalo, JaVale McGee, and Timofey Mozgov.

[12] The Lakers developed young stars Julius Randle, Brandon Ingram, Kyle Kuzma, Lonzo Ball, Jordan Clarkson, Josh Hart, and Alex Caruso before the arrival of LeBron James in 2018–19.

[13] He led the team to an 8–8 record and a playoff berth but stepped down from the role after the season following Jalen Green, Jonathan Kuminga, and Isaiah Todd all being selected in the 2021 NBA Draft.

[15] On the Clippers, Shaw notably coached superstars Kawhi Leonard, James Harden, Russell Westbrook, and reunited with former Pacers star Paul George.