Damian Lillard trade rumors: How Trail Blazers' NBA Draft pick Scoot Henderson could impact star's future

It has turned into an annual offseason question: Will Damian Lillard and the Trail Blazers really part ways?

After being selected with the No. 6 pick in the 2012 NBA Draft, Lillard has spent the entirety of his professional career in Portland. Each time rumors have surfaced about his future, he has firmly rejected the idea of leaving the franchise.

While it would be easy to once again dismiss the speculation surrounding Lillard, the comments from the man himself and recent reports have suggested a trade involving the seven-time All-Star could happen this summer.

Portland's decision to take point guard Scoot Henderson near the top of the 2023 NBA Draft board may open the door for a Lillard departure.

MORE: Breaking down the winners & losers of the 2023 NBA Draft

How Trail Blazers' draft pick could impact Damian Lillard's future

The Trail Blazers ended the 2022-23 campaign with a 33-49 record and missed the playoffs, putting themselves in position to secure a lottery pick. After the season, Lillard made it clear that he wanted the front office to make a win-now move rather than bring in another young player.

"I don't have much of an appetite for bringing in guys two and three years away from really going after it," Lillard said in April. "I think we get Shaedon [Sharpe] at 19, and he's just different. Just being around him, his disposition, how he listens, his frame, his natural talent and his ability. I think that's enough 19-year-olds. You probably won't find one that will come along the way he has. I'm just not interested in that.

"And this is not a secret. I want a chance to go for it. And if the route is to do that, then that's not my route. I think we're all in line with doing what we got to do to put a team together that we can actually go out there and get something done."

Portland landed at No. 3, giving the organization the opportunity to select Henderson. In addition to Henderson's youth, positional overlap is impossible to ignore.

While the Trail Blazers' rise up the board changed the thought process for the team, Lillard never adjusted his stance.

"Damian Lillard wants to win. He wants to win now. He wants to compete for a title," Bleacher Report's Chris Haynes said on the "Dan Patrick Show" earlier this month. "I don't think he believes that taking that pick and keeping it is gonna do them any service in the now. ...

"If they keep that pick, whether it's Scoot or anybody else, I think a serious conversation would be had about potentially parting ways."

Only hours ahead of Thursday night's draft, ESPN's Brian Windhorst reported on "Get Up" that teams are "preparing their offers" if Lillard doesn't react positively to the Trail Blazers' draft strategy.

"They are already getting ready, waiting for the moment to happen," Windhorst said. "Whether Lillard makes the move or the Blazers make the move, nobody seems like they want to be the fall guy here. Lillard doesn't want to look like the bad guy.

"The Blazers still are hoping to convince him to stay, but we'll see how long they continue with that position."

.@windhorstespn says teams are "preparing their offers" for Damian Lillard 👀

"Anybody who would look at Dame Lillard ... Who asked [the Blazers] to go in a different direction and they draft anyway would say to him, 'It's time to go.'" pic.twitter.com/z3j9WneyU5

— Get Up (@GetUpESPN) June 22, 2023

Can the Heat pull off a Damian Lillard trade?

Miami has been the most obvious landing spot for Lillard if he does truly become available. 

Shortly after the news broke that Bradley Beal would be heading to Phoenix, Haynes noted that the Heat were locked in on Lillard. They held a "genuine belief this could be the offseason the veteran guard seeks a change of scenery," per Haynes.

However, on Wednesday's edition of "The Pat McAfee Show," ESPN's Adrian Wojnarowski reported that the Trail Blazers haven't shown any interest in discussing a Lillard trade.

"I think Miami, they're going to be very anxious to watch what happens in Portland to see if there's any point this summer where Damian Lillard becomes available," Wojnarowski said. "He's not available now. He says he wants to be in Portland, and the Blazers have shut down anybody who's called about the possibility of trying to trade for him.

"But certainly, [Heat president] Pat Riley is always going to be real aggressive in trying to improve his team. They want to make that last step. I'm sure they're gonna continue to be real active this summer."

"Miami is very anxiously waiting to see what happens in Portland..

As of right now the Blazers have shut down anybody who has called for Damian Lillard"@wojespn #PMSLive pic.twitter.com/5hhZZPniDB

— Pat McAfee (@PatMcAfeeShow) June 21, 2023

Damian Lillard contract details

Lillard signed a two-year, $122 million extension with the Trail Blazers in 2022. His current deal runs through 2024-25, and his extension will take him through the 2026-27 season if he accepts his player option.