9. Re-signed Meyers Leonard in 2016
The Blazers drafted Leonard 11th overall in 2012, and he showed improvement in his first four years. The seven-footer never broke into the starting lineup, but he averaged 8.4 points and 5.1 rebounds in 21.9 minutes per game just before he became a free agent.
Leonard was also helped by the massive cap spike in 2016. The $24.1 million increase left every team with money to spend, and the 24-year-old inked a four-year $41 million contract to stay in Portland.
Leonard’s playing time decreased immediately. He never worked his way into a starting role as the seven-footer averaged 5.2 points, 3.2 rebounds, and 1.0 assist in 14.0 minutes per game over the next three seasons combined.
The Trail Blazers traded him during the 2019 offseason in a four-team deal that sent Hassan Whiteside to Rip City. Whiteside’s stay lasted just one season but was a significant upgrade over Leonard.
Meyers Leonard was the 114th highest-paid player in the NBA in the 2016-2017 season as he made nearly double the mid-level exception. It was a disastrous deal that the Blazers luckily got out of a year early. Leonard never reached his ceiling, which meant the Portland Trail Blazers were stuck overpaying him for years.