Portland will send a future second-round pick to the Magic for Harkless.
Harkless was the 15th overall pick in the 2012 NBA draft, but never fully met his potential in Orlando. Only 22 years old, Harkless is still a young player with upside and a sensible acquisition with little risk for the Blazers as general manager Neil Olshey reshapes the roster post-LaMarcus Aldridge and Wesley Matthews.
Portland has a need at small forward and Harkless will get an opportunity with the Blazers.
The Blazers are awaiting Oklahoma City's decision on matching a $70 million offer sheet for restricted free-agent center Enes Kanter. That deadline is midnight ET on Sunday.
Portland brings Harkless into a team that has added such young players as Mason Plumlee and Noah Vonleh in trades this summer. The Blazeers signed Ed Davis, and Al-Farouq Aminu to go with All-Star point guard Damian Lillard, Meyers Leonard and C.J. McCollum.
Harkless averaged 3.5 points last season and 6.8 points in his three NBA seasons in Orlando.
More NBA coverage: