Everyone knew the move was coming: The Portland Trail Blazers would trade Damian Lillard and reset the franchise. The only question was when and to where. Would general manager Joe Cronin finally relent and accept the Miami Heat's offer? Were there even other offers on the table?
The drama lingered through the summer and almost into October before the Milwaukee Bucks shocked the NBA world and swooped in to acquire Lillard, pairing him with Giannis Antetokounmpo and resetting their own franchise to make another title run. Included in the three-team deal was Jrue Holiday, who had no place in Rip City as a veteran star looking to win another title himself.
The Trail Blazers set themselves up for a part two of the Lillard trade
Not only did Cronin hold out and land a much better Milwaukee package instead of caving and accepting a sub-par Miami bundle, he made the smart move to grab a two-time All-Star and NBA champion point guard. He could flip Holiday to a contender, piggybacking the offseason's biggest trade with a second massive deal for another haul of assets.
Portland received Deandre Ayton, Toumani Camara, an unprotected 2029 Bucks pick and two Milwaukee pick swaps for Lillard. Now the Blazers had a five-time all-defensive team floor general and Olympic Gold Medalist to sell as well.
The current outlook on the Jrue Holiday trade
Things have certainly worked out for the Celtics, who have the NBA's best record and a 14-game lead on Dame and the Bucks for the top seed in the Eastern Conference. As a refresher, here's the trade in its entirety:
Since the Blazers were transitioning into complete rebuild mode, the best course of action was to land as many future assets as possible. Dame brought back a young franchise center and at least one valuable first-round pick, if not more (and, as it turns out, a piece of the long-term puzzle in Camara).
In exchange for Jrue, Cronin landed a second veteran guard in Brogdon; a young, cost-friendly big man in Williams who, along with Ayton, could potentially create the best center duo in the league; and two future firsts, one in the upcoming draft and another potentially premium selection down the line.
Regrading the Holiday trade
It's not easy to separate this deal from the Lillard deal; they're two pieces of the same puzzle, and combined, they earn Cronin an "A". But ignoring the Dame return and simply examining this move as if the Blazers had Holiday all along and traded him to Boston, it's easier to pick the move apart one asset at a time.
The snap judgment on acquiring Brogdon was that he was another veteran guard who would be shipped out in a much smaller part three of this deal. Shortly after the trade was made official, though, Cronin said he had no intention of moving the 31-year-old before the season. He valued his leadership and intelligence on a young team.
Brogdon hasn't played since the all-star break. He has a fairly long injury history and he developed some issues in his elbow in mid-February. If Portland was competing for a postseason spot, there's a good chance last season's Sixth Man of the Year would be back on the court. But the Blazers aren't so he isn't.
Still, he was a critical part of Scoot Henderson's development in multiple ways and was useful when he was on the floor, averaging 15.7 points and 5.5 assists while shooting 41.2 percent from three.
Williams, who has a much longer injury history, has been a complete non-factor. Even though the Trail Blazers held the 26-year-old out of every other game to avoid another major injury, it only took six games for Time Lord to tear ligaments in his knee and require season-ending surgery.
The 2029 Celtics pick holds legitimate value. Holiday will be retired by then, Kristaps Porzingis will likely be on a beach somewhere with him, and who knows where Jayson Tatum and Jaylen Brown will be at ages 31 and 32, respectively. And the Warriors' down season has been a pleasant surprise for Portland, which will likely end up with a second lottery pick this summer.
Additionally, there's still a likelihood that Brogdon and Williams will be traded at some point. Malcolm was reportedly worth a protected first-round pick at this year's trade deadline, and there was rumored interest from the Houston Rockets in Williams, who may be worth at least a pair of second-round selections.
This trade is still incomplete. Both players the Blazers received will be moved on for more assets at some point. What Cronin decides to do with a late lottery pick is still to be determined. And what value Portland gets from an unprotected Celtics' pick five years from now will remain a mystery for a while. But all that factors into the grade the Trail Blazers deserve for the Holiday deal.
Blazers trade grade: B