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Brad Stevens shook up his roster this offseason, and with the assets he traded away, it’s fair to question whether or not he pursued the most valuable return

By Danny Picard

BOSTON — I hate to interrupt the Brad Stevens “Executive of the Year” Coronation, but before you go placing the crown on that man’s head for acquiring Kristaps Porzingis and Jrue Holiday, I need to share something with you.

What I’m about to say will probably sound blasphemous, as you continue to celebrate the Boston Celtics’ current mastermind. But here it goes: Danny Ainge would’ve traded for Damian Lillard instead.

This isn’t something you want to hear right now. I realize that.

You most certainly don’t want to agree with it. And how could you? You’ve already made these new-look Celtics the favorite to win the NBA Championship next summer. You’ve turned Porzingis into Luka Doncic. And you’ve described Holiday’s defense to me as if his nickname was “The Glove.”

You love this team and the moves Stevens has made. So why would you even want to consider any criticism thrown his way?

You won’t stand for any of it. Fine. But at least think about this.

What if the news, back in June during the week of the 2023 NBA Draft, was that Stevens traded Marcus Smart, Malcolm Brogdon, a 2029 first-round draft pick, and multiple first-round pick swaps (the equivalent of Milwaukee’s package of Holiday, Grayson Allen, and the first-round pick/pick swaps) in a three-team deal with the Portland Trail Blazers and Phoenix Suns, that landed Lillard in Boston? Would you be upset that Stevens didn’t take those same assets and make two separate trades to acquire Porzingis and Holiday instead?

Of course you wouldn’t.

You’d be celebrating the Celtics’ new “Big Three.” Your comparisons to the Kevin Garnett trade in 2007 would never stop. But more than anything, you’d be obnoxiously praising Stevens for making “a Danny Ainge deal.”

Obnoxious or not, I’d be right there praising him with you. Because it would be true. That would be “a Danny Ainge deal.” Compile assets, target a bonafide veteran superstar who’s tired of playing for the same losing organization his entire career, get creative with a trade that previously seemed impossible. That’s what Ainge did to pry Garnett from the Minnesota Timberwolves.

And something’s telling me that if Ainge was still with the Celtics, he would’ve done the same thing to acquire Lillard this offseason.

It should be noted that the circumstances are somewhat different at the moment here in Boston, given the Celtics’ success in recent years with All Stars Jayson Tatum and Jaylen Brown. So you could make the case — and I’m sure you will — that these C’s “don’t need” Lillard to win a championship.

Maybe you’re right. Maybe they can win with this group, if Porzingis stays healthy, and if Holiday can be a little more trustworthy than Smart behind the three-point line. But I’ll tell you what isn’t an “if.” And that’s Lillard being an elite scorer for the final three years of his current contract — four years if he opts in for 2026-27.

It’s a superstar league. The old “there’s only so many balls to go around” line has proven to be false-advertising. Just ask last year’s Celtics, who were desperate for another elite scorer when Tatum and Brown combined to shoot just 20 percent from three-point range (18-for-90) in the Eastern Conference Finals, or when the entire Celtics team shot just 21 percent from three (16-for-77) in the final two games of that series.

I’m truly amazed at the number of people who complained about Tatum’s scoring droughts and Brown’s turnovers during the playoffs, only to turn around now, several months later, to tell me Lillard wouldn’t be a good fit here.

Having an additional elite scorer like Lillard last season would’ve put the Celtics in the NBA Finals for the second straight year, for sure. Lillard finished third in the NBA in scoring, averaging 32.2 points per game. And he was third in the league in three-pointers made per game, with 4.2, behind only Steph Curry (4.9) and Klay Thompson (4.4).

It’s called superstar insurance. And it should be pursued and embraced. Holiday isn’t on Lillard's level, and the only insurance we should be worried about with Porzingis is his health insurance.

Yet, you’d still rather have those two instead of Lillard? OK, fine. But I think you’re crazy.

I just have a tough time seeing that the Bucks acquired the best player available this offseason, when it was the Celtics who traded away more assets. As I mentioned on my latest podcast, here are the notable Net Exports from both the Bucks and Celtics in the aforementioned trades:

Celtics Net Exports:

-Marcus Smart

-Malcolm Brogdon

-Robert Williams

-1st Round Pick in 2029

Bucks Net Exports:

-Jrue Holiday

-Grayson Allen

-1st Round Pick in 2029

The Celtics also gave away irrelevant players like Danilo Gallinari and Mike Muscala, and both teams made additional pick swaps, but that’s why I described the above trade chips as “net” exports.

Had you told me before the offseason that this is what the Bucks and Celtics would trade away, and then asked me, “Which of these two teams will acquire Lillard?” I wouldn’t even blink before answering, “The Celtics will get Lillard if they’re willing to give up that much, obviously.”

Credit to Stevens for his creativity this offseason though. It was an admirable effort to improve the team and fill some holes, no doubt. To me, it feels more like 2004 Theo Epstein than it does 2007 Ainge, but the good news is, both of those teams ended up winning championships.

Still, I do wish Stevens had been the one to get Phoenix involved — back in June — as the third team in a blockbuster deal with Portland to bring Lillard to Boston.

He didn’t. And so, last week, Bucks general manager Jon Horst did, making the type of trade that wins you the NBA “Executive of the Year” award.

Sorry to ruin the party.

Follow Danny on instagram @DannyPicard.


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