Extratime debated that exact question on their latest show, with Portland qualifying for the continental tournament after winning the MLS is Back Tournament this past August. They're one of four MLS teams already into the 2021 edition, while Toronto FC could still qualify via the Canadian Championship route.
For Matt Doyle, Portland's potential CCL success will come down to tactical decisions from head coach Giovanni Savarese, particularly along the backline.
"It's almost more tactical than it is personnel-related for Portland," Doyle said, "because even if they upgrade those two spots, right back and center back, just the way they play when they're giving up possession, it really, really hurt them last year. And so it's something that Gio Savarese has to figure out on a tactical and a strategic level just in terms of who we are as a team."
To elaborate further, Doyle pointed to Portland's Audi 2020 MLS Cup Playoffs exit at the hands of FC Dallas. That's when they allowed a late Ricardo Pepi equalizer and then fell on penalty kicks, raising some caution in Doyle's eyes.
"If you watched the way the Timbers played last year, any time they were conceding possession, they were going to concede lots of shots, lots of good shots, which is why they were a disastrous team over the final 15 minutes of every single game they had a lead or were tied in," Doyle said. "And we saw that into the playoffs, where they went up 1-0 on FC Dallas and then inevitably in stoppage time gave up the equalizer."
For more from Extratime, check out the clip above and listen to the entire show here.