NBA Mailbag: Damian Lillard's Future, the Up and Down Celtics and More

What does the shakeup in Portland mean for the future of their franchise superstar?

With more than a quarter of the season in the books, let’s open up the Mailbag for your questions on the Blazers, the Coach of the Year race, a (fictional) LeBron return to Cleveland, the up and down Celtics and the next coach of USA Basketball …

What does the shakeup in Portland mean for the future of Damian Lillard? -Stephen, Eugene, Oregon

Lot to unpack here. Let’s start with what Damian Lillard wants. The Athletic reported this week that Lillard has voiced support for a deal that would bring Ben Simmons to Portland. I’ve heard the same. The Sixers and Blazers discussed such a swap in the preseason, but Philly’s steep price—C.J. McCollum, three first round picks, for starters, I’m told—ended those talks quickly. But Lillard likes it. He’s been vocal about his desire to see Portland’s roster change. Simmons, if he’s right, would instantly improve one of the NBA’s worst defenses and energize an up-tempo offense. Olshey’s unwillingness to make the deal led to some friction between the ex-GM and the franchise star.

Lillard wants to get paid. Next summer, Lillard is eligible to sign a super max extension that will tack two more years on to his contract. Lillard has conveyed that he wants that offer, I’m told. An extension would add another $106 million to Lillard’s deal and tie him to the Blazers until 2027, when Lillard will be 37. While there was nothing Olshey could do about that now, I’m told the Olshey-led front office wasn’t sold on offering that extension.

Now—to your question. I don’t believe Lillard will be traded in-season. Joe Cronin is the interim GM, and while he has been fully empowered to make basketball moves, I can’t see Jody Allen signing off on a Lillard trade unless Cronin, a candidate for the permanent position, is given the job.

What I can see is Portland making a deal involving McCollum. Maybe it’s for Simmons, maybe it’s for someone else. But in an effort to salvage the Lillard Era, I can see Cronin being open to dealing his second-best asset. As I wrote last week, Olshey didn’t want to trade McCollum. He drafted him, invested in him and Olshey believed a Lillard-McCollum core could win. Cronin may—and likely will—have a different mindset. Maybe a trade works, and the Blazers can continue down a path of building around Lillard. And if it doesn’t, well, Portland can go into the offseason with the knowledge that they tried.

At this point in the season, why is Steve Kerr more deserving of Coach of the Year compared to someone who doesn’t have a Steph Curry or Draymond Green cheat code, like say Billy Donovan? -@IaintMoody

I don’t look at it as Kerr being more deserving than Donovan. Donovan is a strong candidate. How many questions did we have about the Bulls defensively this season? They are inside the top-ten in defensive efficiency and rank in the top half of the NBA in deflections, steals, opponent turnovers and scoring off opponent turnovers. But don’t dismiss Kerr just because he has Curry. Kerr’s work at developing some of the Warriors key role players (Jordan Poole, Damion Lee, among others) is a big reason why Golden State is atop the Western Conference. And they still don’t have Klay Thompson.

Still, and I know you didn’t ask, but my first quarter Coach of the Year vote goes to Monty Williams. The Suns have picked up right where they left off last season, while Williams has helped Phoenix navigate some significant off the court issues. Early on it was Deandre Ayton’s failed extension negotiations—Ayton, to his credit, hasn’t sulked and is once again the anchor of one of the NBA’s top defenses—and then it was the accusations of inappropriate behavior leveled at team owner Robert Sarver, charges the league is still investigating. That the Suns have powered through all of that is a credit to Williams, giving him an edge over a very good field of candidates.

If LeBron were moved to the current Cavaliers, what would that team’s expectations be? Would they be better than the Lakers with LeBron? - @AllenUNC89

Kirby Lee/USA TODAY Sports

Interesting question. James always has championship expectations but you can certainly argue they would be lower in Cleveland because a) it’s Cleveland, not Los Angeles and b) there is no Anthony Davis. Still—would a LeBron-led Cavs team be better than the current Lakers? Cleveland is a middle-of-the-pack three-point shooting team, so there could be similar spacing issues, especially with a team that starts two bigs in Jarrett Allen and Evan Mobley. But the Cavs have a top-five defense. They have an emerging star in Darius Garland. They have Mobley, who has been favorably compared to a young Davis. And LeBron could probably extract more out of Kevin Love. The Cavs are younger and more athletic. Let’s just say this—it’s probably close.

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So where do you stand on Boston? Some nights they look like a team that can contend in the conference. Other nights (more nights) they look like a team that needs to shake things up. – Edward, Melrose

I like what I’ve seen offensively from Boston lately. The offense is finally clicking. They scored 130-points in a loss to Utah and drilled Portland for 145. Jayson Tatum has had a heavy workload of late but Tatum has responded by playing some of his best games of the season. Dennis Schröder has been excellent, Grant Williams is shooting 43.2% from three while Al Horford has picked up right where he left off three seasons ago. There are a lot of questions about the Tatum-Jaylen Brown dynamic, but I’m a believer in it. They just need more time on the floor together.

What concerns me about Boston is the defense. Look up and down that roster—they don’t have many minus defenders. Schröder, Marcus Smart and Josh Richardson are high level perimeter defenders. Tatum, Horford and Brown are solid up front. Robert Williams is one of the NBA’s best shot blockers. Statistically Boston is a good defensive team—ninth in defensive rating, per NBA.com—but they have had far too many clunkers. Utah dropped 137 points on them at the start of this current road trip. Brooklyn put up 123 in a win over the Celtics last month. This is a team with the talent to be a top-five defense. And to have a shot at being more than first round fodder come April, they have to be.

Who should be the next coach of USA Basketball? – Stephen, Dallas

Gregg Popovich, the outgoing USA Basketball coach, remarked this week that USAB was getting closer to a decision on the next coach. The obvious choice is Steve Kerr, who worked as Pop’s assistant in ’19 and ’21. Kerr is accomplished, well-liked and his free flowing offensive system would likely work well at an international level.

If there was a dark horse candidate it’s Erik Spoelstra, the Heat coach who popped up on the USA Basketball scene for the first time last summer, coaching USA Basketball’s Select Team. Spoelstra, 50, is one of the younger potential candidates, which could be meaningful if Grant Hill, who has taken over for Jerry Colangelo as the head of the program, wants to establish some continuity with the program by tabbing a coach who will work multiple Olympic cycles, as Mike Krzyzewski did. Spoelstra’s international coaching experience is limited—a factor Hill will undoubtedly consider—but he’s one of the NBA’s brightest coaching minds who has proven he can coach a team loaded with stars.

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