Portland Bought a Young Wing for Almost Nothing
Portland acquired Maurice Harkless from Orlando in July 2015 for a conditional 2020 second-round pick. Harkless was only 22 and had just fallen out of the Magic rotation, so the Trail Blazers were buying upside at a very small acquisition cost. The bet worked immediately. Harkless appeared in 78 games in his first Portland season, moved into the starting lineup late in the year and then started all 11 playoff games as the Blazers reached the second round.
Harkless Became a Four-Year Rotation Staple
The first season was not a one-year spike. Harkless spent four seasons in Portland, appearing in 274 regular-season games and starting 173 of them. His best shooting year came in 2017-18, when he hit 41.5 percent from three, and he remained a useful defender and transition finisher even when his offensive role changed. He also played 33 playoff games for the franchise, starting 32, including 16 starts during Portland's run to the 2019 Western Conference Finals.
Orlando's Conditional Pick Produced No Drafted Player
Orlando later sent the Portland 2020 second-round right to Cleveland in the January 2016 Joe Harris transaction. That pick was protected from Nos. 31 through 55. Portland ultimately used its own No. 46 selection in 2020, so the protected obligation did not transfer to Orlando or Cleveland. Portland, meanwhile, received years of real rotation value from Harkless.
This Low-Cost Bet Paid Off for Portland
The Trail Blazers were rebuilding their supporting cast around Damian Lillard after losing several veterans in the 2015 offseason. Harkless fit that timeline, improved enough to earn another contract and became a dependable starter on playoff teams. Orlando had understandable reasons to clear a crowded wing rotation after Harkless' poor 2014-15 season, but the return never developed into comparable value. The canonical A for Portland and C+ for Orlando fit the difference between a four-year contributor and a conditional pick that never conveyed.
Final Verdict
Blazers Win — Portland A, Orlando C+. Portland acquired Maurice Harkless for a conditional 2020 second-round pick and received 274 regular-season games, 173 starts and four playoff runs from him. Orlando later rerouted the conditional pick, and the protected Portland obligation ultimately did not convey because the Trail Blazers' 2020 second-rounder landed at No. 46. Harkless became a useful long-term wing on teams that repeatedly reached the postseason.