Canzano: Damian Lillard trade is a chance to see what might have been

Trail Blazers trade seven-time All-Star.

Damian Lillard was traded to Milwaukee on Wednesday. (Photo: Naji Saker)

You knew it was coming. I did too. The saga had become exhausting and the distraction too difficult to ignore. Still, I found myself a little somber in the aftermath of the trade of Damian Lillard on Wednesday.

The seven-time All-Star is gone.

The Blazers moved on.

Before everyone scatters, one truth — the Lillard era should have been so much more. More fun. More winning. More playoff confetti. That it fell short on those fronts goes down as one of the biggest misfires in franchise history.

After months of uncertainty, cryptic social media posts, the unfollowing of his team on Instagram, the Trail Blazers traded Lillard. I get why they did it. And I understand why Lillard wanted out. But I wonder if the involved parties realize their union could have been so much more fun.

Zero playoff victories beyond the second round. A single appearance in a Western Conference Finals — where the Blazers were promptly swept. No parade. No champagne. No banners. And not nearly enough to smile about as we all watch one of the franchise greats pack for some another NBA town.

It was a three-team trade. Portland gave up Lillard, Jusuf Nurkic, Nassir Little and Keon Johnson. In return the Blazers reportedly got Jrue Holiday, Deandre Ayton, Toumani Camara, Milwaukee’s 2029 unprotected first-round pick, and unprotected swap rights in 2028 and 2030. Phoenix receives Nurkic, Little, Johnson and Grayson Allen.

I imagine Portland fans texted each other in the aftermath, sorting through the particulars, trying their hardest to fall in love with the trade. Coach Chauncey Billups has to be pleased, as his defense got better and the narrative for next season shifted in a positive direction. It’s his team now, truly — and finally.

Blazers’ general manager Joe Cronin may not be done. But it’s not a bad trade at face value for the Blazers. Better than what Miami was offering. And it avoids an uncomfortable scene at the team’s upcoming media day and skips the soap opera that would have clouded Portland’s training camp.

Lillard asked for a trade. He demanded Miami. The Blazers sent him to Milwaukee instead. On social media Lillard wrote: “Excited for my next chapter!” But I wonder if he pumped a fist or threw his duffle bag across the room. This whole thing started with Lillard’s suitcase thinking “swim trunks” but ended with “parka.”

Aaron Goodwin, Lillard’s agent, told a reporter for The Miami Herald: “(The Heat) did everything they could to acquire Dame. It takes two to get a deal done.”

Heat star Jimmy Butler took to social media with a message to the NBA: “Y’all need to look into the Bucks for tampering. Y’all do. I’m just going to put that out there. Y’all didn’t hear that from me.”

I definitely did hear it from Butler. We’ll see how it unfolds. The Bucks won the trade big-time on paper. They got a true star. But given that the Lillard era in Portland often underdelivered I’m fascinated to see what happens next in Milwaukee.

Jusuf Nurkic and Damian Lillard were both traded. (Photo: Naji Saker)

Championship? Or bust? I guess I’m asking if the underachievement in Portland had more to do with Lillard or the Blazers? I suspect it was the rudderless franchise, but it’s a question to ask as we wait to see whether Lillard can deliver a third NBA championship to the Bucks.

He’s a gifted offensive player, but is challenged defensively. Will that matter as much on Milwaukee’s roster? And how will Lillard fit alongside another super star player?

Giannis Antetokounmpo isn’t just an All Star. He’s a two-time MVP who already won a championship. I wondered every summer why star free agents didn’t pick Portland. Was it the franchise? The small media market? Or did they not see themselves being able to shine with the ball so frequently in Lillard’s hands?

The Bucks and Giannis give Blazers’ fans an opportunity to see what might have been with Lillard. Because with stronger ownership and better management it could have been Portland — not Milwaukee — who went all-in years ago on a trade for a perennial All-Star.

We all knew Lillard would eventually be traded. Now? Later? And for what? Those were the only questions. Meanwhile, the Blazers shaped their entire media day around trying to make things less tense.

The team issued an advisory earlier this week indicating that the president, GM and coach would take questions as part of a panel interview next Monday. Then “Trail Blazers players” would be made available, presumably on stage.

“There will be no one-on-one interviews on Media Day and no member of the media should approach players for an interview,” the advisory said.

Forget all that now.

The guy everyone wanted to hear from is gone to Milwaukee.

We all knew Damian Lillard would be traded. It had to happen. The Blazers needed to go free. Lillard wanted a fresh start. Fans were over it, too. But there’s a melancholy undertone to this whole thing.

All the hope and joy in Milwaukee today should have belonged to Portland.

---

Thanks to those who support this independent publication with a subscription. If you’re not already a paid subscriber consider one here or buy a gift subscription for a friend or family member:

This is an independent reader-supported project with both free and paid subscriptions. Those who opt for the paid edition are providing vital assistance to bolster my independent coverage. Please consider becoming a paid subscriber to have full access to all of my posts.