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Portland coach Chauncey Billups thinks Damian Lillard and Trail Blazers will reconcile after acrimonious trade saga

DETROIT — Portland Trail Blazers head coach Chauncey Billups knows it seems far away in the wilderness, but he sees a day where a reconciliation happens between Damian Lillard and the Trail Blazers franchise.

The wounds from the acrimonious divorce are still fresh from Lillard’s summer trade request and subsequent move to the Milwaukee Bucks. It was a sour ending to over a decade of Lillard representing the franchise, becoming an All-NBA and Top 75 player.

Lillard is the all-time franchise leader in several categories, including scoring and points per game — and second in assists.

“Sooner or later, talks will be had,” Billups told Yahoo Sports recently. “Emotion will be down and that will heal itself. I really believe that.

“At the end of the day, what Dame did for the organization has never been done before. He’s gonna go down as the greatest. And also what this organization did for Dame was incredible. They had an incredible two-way relationship for the entire time.”

Portland Trail Blazers head coach Chauncey Billups talks to Damian Lillard during a 2022 game. Lillard was traded to the Milwaukee Bucks before this season. (Photo by Jason Miller/Getty Images)
Portland Trail Blazers head coach Chauncey Billups talks to Damian Lillard during a 2022 game. Lillard was traded to the Milwaukee Bucks before this season. (Photo by Jason Miller/Getty Images)

Billups has a unique perspective on matters. As a player, he was moved multiple times — both as a player trying to establish himself in the league, then as a franchise leader, and then even as part of a trade request, although not his own but by virtue of Carmelo Anthony’s trade request out of Denver in 2011.

Billups was also thought to be more of a front-office type than a head coach, even going through the interview process with the Cleveland Cavaliers in 2017 before withdrawing and becoming a TV analyst.

He stayed out of Portland's trade talks, though, leaving that to general manager Joe Cronin. Some coaches want minute-by-minute updates, and others don’t want to go through the highs and lows.

“Until it got to a point where it was real. Then, it’s, ‘Let’s talk about it,’” Billups told Yahoo Sports. “But I wasn’t in the day to day. It’s not my job. Obviously, it impacts my job. You stay close enough or far enough to trust Joe and his staff to do their thing and to have me in mind.”

Even before becoming Lillard’s coach for two years, the two were close. That relationship strengthened through the proximity they shared in Portland, and the relationship has stayed strong even through the franchise strife.

“We’ve had several [conversations], even when it first started [the trade request],” Billups told Yahoo Sports. “I already knew, even however this goes, it’s not gonna change our relationship, our friendship. We talk about very personal things, we talk about hoop at times. And we’ve talked several times since it’s been over. I’m happy for him.”

Lillard is finding his way with the Bucks, averaging 24.3 points, 4.7 assists and 4.4 rebounds on 40% shooting and 29.3% from 3-point range. Billups has seen player-team divorces affect personal relationships in his playing days and was going to make sure that wasn’t the case here.

He acknowledged how emotional it was, even becoming toxic when it was perceived Lillard wouldn’t get to his preferred destination, the Miami Heat. The Bucks largely swooped in at the last second, making a deal days before training camp began.

“We all felt it, on the daily,” Billups told Yahoo Sports. “It’s something coming out every day. You can’t run away from it. You can’t ignore it. At all. You give it the little you give it at the time, knowing there’s little you can do to affect it, and you keep it moving.”

But one day he feels Lillard will be welcomed with open arms by the franchise and by the fans. He’s seen it and been part of it too many times.