Portland Trail Blazers guard Damian Lillard Troy Wayrynen-USA TODAY Sports

Damian Lillard has been relatively open about his displeasure over how the Portland Trail Blazers have handled themselves this offseason.

First, Lillard expressed disappointment with how the team’s coaching hunt went, then he revealed frustration about his team’s approach to free agency over the summer.

Despite all this, Lillard never came out and actually demanded a trade. His representatives later revealed why in a leak to the media. That means, for better or worse, he is tethered to Portland for the foreseeable future.

But how long exactly is that?

According to Shams Charania of The Athletic, if Portland ultimately gets off to a bad start, there is a chance Lillard demands out.

“I think there’s going to be a light going into this upcoming NBA season on the future of Damian Lillard,” he said. “And if Portland gets off to a rough start, like, I’ll tell you guys this if they’re not improved under Chauncey Billups this year, they risk losing Damian Lillard long term.”

Billups recently came out with a rather blunt message to Lillard regarding all the trade chatter. Clearly it is wearing on both him and the organization.

If the Blazers can’t get off to a good start, it’s not difficult to see a scenario where all this gets blown up.

Many around the league have said they believe Lillard will be a member of the Boston Celtics by Christmas.

Will that prediction actually come to fruition? Time will tell.

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