Six goals were traded as the Timbers overcame an early red card to keep at least one point on home turf.
With the Crew coming into the game winless in seven and and on a three-game losing skid, Portland looked ready to exacerbate those recent struggles with an early goal. Steve Zakuani's through ball split two Crew defenders en route to Maximiliano Urruti, who recovered from a poor first touch to turn and roof a shot past Steve Clark.
But Portland hadn't accounted for the individual brilliance of which Federico Higuain is capable. The Portland defense sat back as a fluid Columbus move through central midfield found the Argentine, and given the space, he sensationally chipped Donovan Ricketts from 25 yards out.
Alvas Powell was sent off for a brutal challenge in the 34th minute. The right back slammed into Chad Barson and flipped the Crew defender end over end in midair, and referee Carlos Rivero wasted no time in brandishing the red card.
The man in the middle would again punish the Timbers in the first half. Futty Danso was whistled in the box for pulling down Giancarlo Gonzalez, and Higuain converted to put the visitors ahead.
The Timbers thought they had done enough for a draw when a 80th-minute goal from Will Johnson brought things back to equal status at 2-2, but the Crew responded immediatey.
Barely seconds after the restart, the Crew again jumped ahead, with Ethan Finlay's shot deflecting off Danso and into the goal to make it 3-2 in the 81st.
Portland refused to stay down though. Gaston Fernandez scored his team-leading fifth goal of the season to earn his club a 3-3 draw in a thrilling spectacle.
The Timbers lift themselves out of the bottom of the Western Conference with a 1-3-7 record. Columbus is now 3-4-4.