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Grade the trade: Blazers deal Lillard to Bucks (updated with Holiday return)

Andrew Hanlon
Andrew Hanlon

Rip City Project

Damian Lillard, Portland Trail Blazers, Credit: Rob Gray-USA TODAY Sports

Note: This piece originally ran just hours after the Damian Lillard trade was complete. It’s been updated to include the Jrue Holiday trade to the Boston Celtics.

The inevitable has finally happened: The Portland Trail Blazers made their Damian Lillard trade – shaking the NBA world to its core in the process – sending one of the best players in franchise history to the Milwaukee Bucks in a three-team deal that includes the Phoenix Suns.

There were whispers over the past few days about the Bucks holding talks with Trail Blazers General Manager Joe Cronin, but Milwaukee’s assumed lack of assets created just a general shrug from most people. Of course they checked in, but there wasn’t really a chance the Bucks had enough to land Lillard.

Now here we are, with Dame heading to the Cream City to chase his elusive championship next to Giannis Antetokounmpo.

Portland Trail Blazers, Milwaukee Bucks, Phoenix Suns combine on Lillard trade

Unlike Milwaukee, it seemed like there was some legitimate truth to rumors that the Phoenix Suns could be the third team in a potential Lillard trade.

As it turns out, that was perhaps the case all along. Maybe Cronin was just waiting for the big, final domino to fall, which happened to be the Bucks making what he felt was the right offer.

But was it the right offer? What grade does the Blazers’ return package deserve?

Jrue Holiday is part of the Portland Trail Blazers trade of Damian Lillard to the Milwaukee Bucks.
Jrue Holiday, Milwaukee Bucks (left); Damian Lillard, Portland Trail Blazers. Mandatory Credit: Jaime Valdez-USA TODAY Sports

Blazers send Lillard to Bucks, Nurkic goes to Suns, Ayton comes to Portland

Deandre Ayton has reportedly been on the Trail Blazers’ radar for months, if not longer. When rumors of Phoenix’s involvement in a Lillard trade started to trickle out, the key part of any deal involving those two teams was an Ayton-Jusuf Nurkic swap.

In a week filled with rumors, most of which turned out to be just smoke, it appears at least one was true.

From a Bucks perspective, the allure of this trade is simple: pair Lillard with Giannis and go win a championship. Oh, the pick-and-roll possibilities with those two…

To get their guy, Milwaukee traded Jrue Holiday – one of the best defensive guards in the NBA and a critical piece of the franchise’s 2021 championship team. In fact, the Bucks won their first title in 50 years the season Holiday arrived in Milwaukee.

The Bucks also sent Grayson Allen to the Suns and a first-round pick in 2029 and first-round pick swaps in 2028 and 2030 to Portland.

Phoenix sends Ayton and Toumani Camara to the Blazers in return for Nurkic, Allen, Nassir Little and Keon Johnson.

Update: Blazers trade Jrue Holiday to the Boston Celtics

It’s easier to look at this deal as a whole now that each part of the trade is complete.

Portland flipped Holiday to Boston in exchange for Robert Williams III, Malcolm Brogdon, the Golden State Warriors’ first-round pick in 2024 (top-four protected) and the Celtics’ first-round pick in 2029.

It was another waiting game to see what would happen with Brogdon – as another veteran guard, would he be rerouted the way Holiday was? Would the Lillard trade become a trilogy?

As it turns out – at least to begin the season – that won’t be the case. The 30-year-old former Rookie of the Year will be sticking around in Portland as the adult in the backcourt room with the 19-year-old Scoot Henderson, 20-year-old Shaedon Sharpe and 24-year-old Anfernee Simons.

The Portland Trail Blazers got Deandre Ayton from the Phoenix Suns in the Damian Lillard trade.
Deandre Ayton, Phoenix Suns (Photo by Christian Petersen/Getty Images)

How did the Blazers do in acquiring Ayton from Phoenix, Holiday from Bucks?

Ayton is the centerpiece of the deal for Portland. He is a significant upgrade over Nurkic.

The No. 1 overall pick in the 2018 draft is only 25 years old, so he fits in comfortably with the Trail Blazers’ youth movement. He’s also a solid fit with the team’s trio of guards, Henderson, Sharpe and Simons. The four of them will be able to grow together over the next several seasons.

Losing Lillard was a given, and trading Nurkic seemed like a good possibility, but shipping out Little is a bit of a surprise, Johnson less so. Obviously, neither of those players were deal-breakers, but Little still holds potential as a three-and-D forward if he can stay healthy. He’ll be a solid rotation piece around Kevin Durant, Bradley Beal and Devin Booker with the Suns.

The most significant question looming over the entire deal is what happens with Holiday. While he would be awesome as a veteran leader for Henderson, Sharpe and Simons, he doesn’t fit with the the roster overhaul or goals Portland has. He certainly can’t have interest in being part of a rebuild, either.

Nabbing Ayton – a nimble, 6-foot-11, 250-pound big man as the long-term answer at center – especially considering his age and fit with the rest of the Blazers’ core – is not nothing. But until we find out what Cronin gets in exchange for Holiday, there’s no way to analyze this deal in its entirety.

Updated: Portland Trail Blazers’ complete Damian Lillard trade return

With the full deal complete – again, for now (Brogdon could potentially be traded during the season or at the trade deadline) – the Trail Blazers’ entire return in the Lillard trade consists of:

  • Deandre Ayton, Robert Williams III, Malcolm Brogdon, Toumani Camara
  • First-round picks from the Warriors in 2024 (top-4 protected), Bucks in 2029, Celtics in 2029 and potential first-round pick swaps from Milwaukee in 2028 and 2030.

So Cronin turned Lillard, Nurkic, Little and Johnson into two athletic, versatile centers for the future – one offensively gifted, the other defensively, but both excellent fits around Scoot, Sharpe and Simons; a veteran combo guard who can stay on the floor in any lineup; a lottery-ticket in Camara; three first-round picks; and two potential first-round pick swaps.

Considering the offers that had been reported prior to the actual trade, this is a home run for Cronin and the Blazers.

Final Blazers trade grade: A

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.