In the aftermath of last summer’s Damian Lillard trade, ESPN’s Brian Windhorst took everyone behind the scenes and into the swift, direct response from rival front offices.
Windhorst detailed how general managers rushed phone lines when the Dame news broke. But GMs weren’t panic-trading to counter the new-look Milwaukee Bucks. Not really.
While fans and media openly gushed over the NBA’s newest and, perhaps, most dangerous duo in Lillard and Giannis Antetokounmpo, teams knew what the Jrue Holiday move meant for contenders.
Title-chasers across the league opened up their war chests widely and immediately.
Because they all saw how Portland’s trade with Milwaukee changed everything.
A Championship In the Making
With Jrue Holiday off to the Portland Trail Blazers (a team avoiding the 2024 title like a 2020 virus), Holiday’s status on the open market became an unexpected “massive opportunity” for contenders, according to Windhorst.
“This is one of the rarest transactions you see in the NBA,” he wrote in a column titled Why Jrue Holiday—Not Dame—Will Impact The NBA Title Race More.
“A league-altering trade,” he called it, “that begets another possible league-altering trade.”
Flash forward to today, and Windhorst’s proclamation looks like the stuff of legend. (Again.)
Holiday was indeed dealt to the contending Boston Celtics. And ahead of Friday’s Game 4 against the Dallas Mavericks, Holiday is on the brink of his second title, all after watching Lillard’s season crash land with the Bucks in Round 1.
As Windhorst both explained and clarified back in September:
“That is not because Holiday is a ‘better’ player than Lillard, who is one of the greatest offensive players of this generation. But because Holiday’s skill set—he’s a voracious defender coming off one of the best offensive seasons of his 14-year career—is so desired by contenders in the league.
“That he’s got championship experience,” Windhorst continued, “and can play a variety of different roles only makes him more valuable on a star-laden team.”
The Big ‘What Ifs?’
Holiday, who was 33 at the time of the deal and turned 34 on Wednesday, has the experience, defense, and on-or-off-ball skills to plug into any backcourt. The Trail Blazers, more than most, were and remain deprived of those first two core characteristics.
Keeping the veteran guard, though, tucked away in the Pacific Northwest was never the plan. Not while the team’s most meaningful wins are being counted in ping-pong balls. And not after Joe Cronin was able to bring in a haul of future assets and (albeit oft-injured) swappable trade pieces.
Then again—this is the NBA, and there’s never a bad time for a game of What If? It’s really never too early.
So let’s ask: What if Portland had held onto Holiday?
Would the star guard have unlocked Deandre Ayton earlier in the year? How would Holiday’s defense and playmaking have made life easier for Anfernee Simons, Scoot Henderson, and Shaedon Sharpe?
Furthermore, which young backcourt member would be relegated to a lesser role?
Holiday is more than a supercharged Malcolm Brogdon set to come off the bench; he’s a starter every which way about it, and if the team isn’t threatening to win big, the sacrifice to long-term pieces just isn’t worth it for anyone involved.
What About Boston?
If you assume the Blazers hold onto Holiday initially, but they remain iffy postseason bets at best, you can also safely assume Holiday ends up the No. 1 target on most contender trade-block big boards come February’s deadline.
This is where Boston’s big “what if?” comes into play because if the Celtics don’t land Holiday during the offseason, the Jrue Sweepstakes in February would have been unlike anything we saw for OG Anunoby or Pascal Siakam.
Don’t believe me? Just ask Jayson Tatum, who said outright, “I don’t know how they let us get him,” post-game on Wednesday.
And when asked where the C’s would be without Jrue, following the soon-to-be two-time champion following his 26-point, 11-rebound game?
Tatum said, with an expression of relief even more so than joy:
“Good thing we don’t have to find out.”
Holiday is one win away from earning his place in Celtics history.
But as they say: Once a Trail Blazer, always a Trail Blazer.
