Blazers Free Agency: How day 1 moves may impact Damian Lillard’s future

Jerami Grant (left), Damian Lillard, Portland Trail Blazers (Photo by David Berding/Getty Images)
Jerami Grant (left), Damian Lillard, Portland Trail Blazers (Photo by David Berding/Getty Images) /

Day one of the 2023 NBA free agency period has come and gone. A lot of money was spent. (Like a lot). Things went pretty chalk for the Portland Trail Blazers, though; a few moves were made, only one of which was unexpected. So is there anything we can glean from the NBA’s moves about Damian Lillard’s future in Rip City?

Day one NBA free agency moves that could affect Blazers, Damian Lillard

Free agency move No. 1: Portland re-signs Jerami Grant

The Trail Blazers’ most significant move of early free agency was also the easiest to call: reaching an agreement to bring back Jerami Grant.

The number – five years, $160 million – is steep. Is Grant a $30 million-plus per year player? Not really, but it didn’t much matter for Blazers General Manager Joe Cronin and Portland’s front office. Lillard expected Grant to be back and PDX needs him to compete, so he’s back. Call it the “Dame Tax.”

Had the organization’s most significant free agent agreed to a deal elsewhere, it would have set off sirens across the NBA that Lillard would be following him out the door shortly.

Re-signing Grant was step one of the “keep Dame in Portland” plan.

Free agency move No. 2: Blazers extend a qualifying offer to Matisse Thybulle

After Grant, Portland’s most important free agent is Thybulle, and sending a qualifying offer his way (before day one of free agency) means that bringing him back should be about 99 percent assured.

Thybulle is a multi-time All-NBA defender; the Blazers couldn’t afford to let him walk. Bringing him and Grant back meant bringing back the team’s two best defensive players, a must for Cronin.

His 38.8 percent shooting from three on 4 attempts per game in Portland was an unexpected but welcome bonus.

Free agency move No. 3: James Harden-Sixers rumors

Re-signing Grant and Thybulle were two moves designed to keep the roster around Lillard stable. Not that the Blazers have any control over this one, but Harden’s expected trade out of Philadelphia muddies the waters, at least a bit.

If The Beard moves on, the Sixers will have gaping holes to fill in the backcourt and on billboards. Dame would be a natural solution to both, and as ESPN’s Brian Windhorst logically put two-and-two together, Philly could come calling for Lillard.

Whatever the 76ers get in return for Harden, coupled with Tyrese Maxey (who looks like a future star) would at least make Cronin and the Blazers have a conversation, however unlikely a trade might be.

Or, to flip things in the complete opposite direction, maybe a godfather offer for Joel Embiid could entice Philadelphia to have a conversation of its own?

Free agency move No. 4: Draymond Green re-signs with Golden State

It was probably a pipe dream all along, but had the Blazers been able to lure Draymond away from the Warriors, any conversation about Lillard leaving Portland would have been snuffed out.

Not only did Dame want Green, but the 33-year-old forward would have been the elixir to most of, if not all, the Blazers’ defensive issues, and he would have brought a veteran presence and winning pedigree no one in Portland has (and Lillard surely wants).

Free agency move No. 5: Letting a trio of players walk

In one of the most confusing moves of the day, Portland decided to waive 22-year-old forward Trendon Watford, who had a promising season last year. He filled in admirably up front, even as a small-ball center at times.

For a team devoid of size and depth, letting a talented young player who was only owed $1.8 million leave for nothing seems odd to say the least, irrespective of any timeline(s) the Blazers choose to be on.

Cam Reddish signed with the Los Angeles Lakers as part of their flurry of day one moves, and Drew Eubanks is taking his talents to Phoenix as part of the Suns’ own frenzy of early moves.

This probably means nothing in terms of Lillard’s future, but the Watford move is weird unless something more is eventually coming down the pike.

Free agency move No. 6: Toronto’s backcourt spending spree

After Fred VanVleet left for Houston and the Lakers pried Gabe Vincent away from Miami, the Raptors were left with a gaping hole at point guard. That created an intriguing opportunity for the Blazers to dangle Anfernee Simons in another attempt to land OG Anunoby or perhaps even Pascal Siakam.

Instead, the Raptors signed Dennis Schroder, who left LA after Vincent arrived, and brought back former Blazer Gary Trent Jr. on a “lucrative multiyear extension.”

There’s still room for Toronto to add to its backcourt, but there’s no major need or desperation to do so like there may have been had Trent and VanVleet both left and Schroder signed elsewhere.

Next. 3 Actually realistic trades to give Damian Lillard a shot in Portland. dark

It’s only day one, and actually shelling out money to sign players was never going to be the real plan for the Blazers this week. If Cronin is going to get anything done to make sure Lillard remains a Trail Blazer, it will almost certainly come via trade. We’re still in a waiting game at this point.