After Signing Damian Lillard, the Portland Trail Blazers Have the Weirdest Roster in the NBA—Fantasy Hoops Fallout
In this story:
Damian Lillard is a Hall of Fame level point guard.
Jrue Holiday is one of the league’s top defenders from the one-spot.
Scoot Henderson was the most sought-after floor general of his draft class.
Shaedon Sharpe is a Swiss Army knife who, at times, has excelled from the point.
All four are excellent basketball players. All four merit a starting job.
Thing is, thanks to Lillard’s return to Rip City, all four are wearing Portland red and black—thus two of them will have to come off the bench. Which means it’s fair to assume that right about now, there are a goodly number of players and agents sending some nasty texts to Blazers head coach Chauncey Billups.
The Return of the Dame
Portland created this potential mess when they signed free agent Lillard—one of the greatest figures in the history of the franchise—to a three-year, $42 million contract, as first reported by ESPN’s Shams Charania.
In another world—a world in which the Blazers didn’t just acquire Holiday—this would be one of the happiest stories of the NBA off-season: An all-time great finishing out his career where it all began.
But as it is, Portland now has a backcourt logjam that could create some agita in Oregon:
- Sharpe went from being arguably Blazers’ most potent offensive backcourt weapon to their sixth or seventh man.
- Henderson’s minutes will take a massive hit, and thus might arrest the development we saw from him at the end of last season.
- Holiday is a team-first guy and would likely come off of the pine without complaint, but making him a backup after trading away an elite scorer (Anfernee Simons) for him wouldn’t be a great look.
- As for Lillard, for that kind of bread, he'll be expected to be the Dame of old. Thing is he's 35 and coming off of Achilles surgery, so who knows.
The whole thing is almost as confusing as what’s happening in Portland's paint.
Meanwhile, in the Middle…
Portland’s center situation is equally odd.
Soon-to-be-sophomore Donovan Clingan is coming off of a stellar rookie season, and his backup, Robert Williams III, if healthy—and that’s a big if—is a near-elite defender. Despite that, the Blazers spent their 2025 first-round pick on raw middleman Yang Hansen, a head-scratching positional choice. Granted, Hansen showed out during the Summer League, but still.
The good news is that things are relatively normal at the forward position, with Jerami Grant slotted in as the undisputed starter at the four, undisputedly backed up my Kris Murray. And Deni Avidja will bop between three and four, with Tourmani Camara wandering between two and three, giving them a versitle, nasty rotation that will help them survive the West.
All of this will make things interesting on the court—it’s so crazy that it just might work—but it’ll make things annoying on the stat sheet.
Meanwhile, In Fantasyland…
Traditionally in fantasy world, Lillard is a first- or second-round option, but the uncertainty about his minutes—an issue that won’t be entirely sussed out until who-knows-when—will make it damn near impossible to figure out where to draft him. If he’s healthy and receiving a full complement of burn, Lillard is a late-first or early-second round choice who will help you dominate in five categories, those being scoring, assists, FT%, threes, and steals.
But that whole surgery and age thing muddies the waters. Like, a lot.
Until about two hours ago, Sharpe and Henderson had fantasy potential oozing out of their respective wazoos, but with Lillard in the building, they’ll lose anywhere from three to ten minutes a night, effectively making them mid-round options who can’t be relied upon on a game-by-game basis. If either falls into the eighth or ninth round, sure, grab them. But not much earlier.
A world-class player and teammate, Holiday's best work doesn’t show up in the box score, thus he’s never been a great fantasy option; unless the Blazers move on from Henderson or Sharpe, that’ll very much be the case in 2025-26.
Holla for D.O.L.L.A.
All that said, NBA fans and fantasy players alike hope Lillard can find the form that made him one of the most dynamic scorers of his era, and one of the top 100-ish players of all time.
If he can be the Dame of old, the NBA will be all the better for it.
More NBA News and Takes From Fantasy Sports On SI
-82121a1351894b8089c555f4b4b69420-1d609352940036e7455770363a74a2e9.png "Alan Goldsher")
Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.