Grading the Craziness of the Damian Lillard Trade
After months of waiting, Damian Lillard was finally traded to…Milwaukee? Huh? Let’s break down one of the most shocking trades…ever.
The Damian Lillard saga and myself had an equally uneventful summer. After 11 years of watching management fumble away his future, Lillard finally decided enough was enough. He demanded a trade to Miami. And then we waited. Days turned into weeks and weeks turned into months. It seemed like neither side would blink and the whole summer would pass before a deal would happen.
And then…BAM! Out of nowhere, the Milwaukee Bucks swooped in to trade for one of the 75 greatest players in NBA history. Let’s break down this complicated mess.
The Trade
Bucks Receive:
- Damian Lillard
Blazers Receive:
- Jrue Holiday (via MIL)
- 2029 unprotected FRP (via MIL)
- 2028 and 2030 unprotected first-round pick swaps (via MIL)
- Deandre Ayton (via PHX)
Suns Receive:
- Jusuf Nurkic (via POR)
- Nassir Little (via POR)
- Keon Johnson (via POR)
- Grayson Allen (via MIL)
It’s Officially Time for a New Era of Blazers Basketball
The past few years have been a slow, depressing decline for the Portland Trail Blazers. They waited too long to fire Terry Stotts and trade CJ McCollum. They tried, in vain, to hold onto Damian Lillard while remodeling the rest of the roster. After back-to-back miserable, losing seasons, it was clear that the franchise needed to make its hardest decision. It was finally time to trade Damian Lillard. Whether he demanded it or not, the relationship no longer made sense to either party.
Lillard is arguably the most important figure in franchise history. He’s certainly the most talented. For 11 years, Lillard was the perfect franchise superstar, both on and off the court. But, sometimes, things aren’t meant to be. Lillard wanted to win in Portland. Badly. Most superstars wouldn’t have put up with as much failure and losing as Lillard. Through thick and thin, he carried an often sub-par roster to relevance. His departure may have been drawn out and bitter, but that doesn’t discount the decade of memories he created before. He’ll always be welcome back to Rip City. Nurkic, too.
For months, I assumed that Lillard was going to Miami. As did everyone. Even though everybody knew Miami’s trade package centered around Tyler Herro and picks was weak, I didn’t think Portland would find a better suitor. In recent weeks, Lillard was at the Blazers’ practice facility, interacting with players and coaches. Dame reportedly let Portland know he was willing to be fully present for the start of the 2023-24 season if only to give the organization more time to work toward a potential trade with the Heat. Joe Cronin and the front office were set on dealing the 7x All-Star before training camp began.
The Blazers re-opened trade negotiations with the rest of the league on September 18th. Teams like Milwaukee, Toronto, Boston, and New Orleans were among those who expressed interest. In the end, the Blazers got a win-win proposal for everybody involved. They got a nice collection of players and picks while rewarding Lillard with the opportunity to win a championship.
Now, Portland can officially turn over a new leaf. It’s time for the Scoot Henderson era to begin. Henderson quickly became an afterthought after he was drafted with the 3rd overall pick in the 2023 NBA Draft. Everyone was focused on Lillard’s trade request. Now, Henderson is the face of a rebuild in Portland, just like Lillard was in 2015. It’s a passing of the torch, from one electric guard to another. Along with Shaedon Sharpe and Anfernee Simons, Portland has a foundation to build on.
The package Joe Cronin secured was better than I had hoped for. Portland turned Jrue Holiday into Robert Williams (!!!), Malcolm Brogdon, and two first-rounders, one of them being an unprotected first from the Celtics in 2029. That pick along with the picks from the Bucks all have a chance to be lottery tickets. There’s no telling where the Celtics and Bucks will be in 5-6 years. But, to me, the most intriguing part of this return is Deandre Ayton.
Ayton fell out of favor in Phoenix due to lackadaisical effort and plateauing production. After Kevin Durant entered the fray, Ayton’s days in the desert were numbered. The former #1 overall pick now gets a fresh start on a rebuilding team. It’s been a while since the Blazers have had a young big with as much potential as Ayton. He’ll be relatively out of the spotlight and could become a mainstay in Portland if things go well. Also, going from a center rotation of Jusuf Nurkic and Drew Eubanks to Ayton and Timelord is quite the turnaround.
It’s a new day in Portland. Tearing teams down is obviously harder than building them up. The process to return to a winning franchise will likely take years. Not having Damian Lillard will obviously make things harder. But, fans should be excited about Henderson and Sharpe and Ayton. The future is bright and more importantly, the team has finally picked a direction.
Grade: A++
The Milwaukee Bucks Are Going For It
Let’s go back to 2020. The Milwaukee Bucks had flamed out of back-to-back playoffs. Some doubt that reigning 2x MVP Giannis Antetokounmpo will re-sign long-term. So what does GM Jon Horst do? Trade five first-round picks to acquire Jrue Holiday from New Orleans. Giannis then signs a supermax extension, and the Bucks win a title. A decent turn of events.
Flash forward to the present, and Milwaukee found themselves in a similar situation. After another disappointing postseason exit where the same offensive problems plagued them, Horst knew changes were needed. Firing Mike Budenholzer was the tip of the iceberg. While Jrue Holiday is one of the best perimeter defenders in the league and was coming off the best offensive season of his career, Milwaukee needed more oompf.
Earlier this summer, Giannis made some comments that surely made Bucks fans squirm in their seats. Antetokounmpo said it “didn’t make sense” to sign an extension this summer. He wanted assurances that Milwaukee was still pushing for a title and would wait until next summer to think about re-upping. I think trading for Damian Lillard will ease his mind on that front.
Sure, the Bucks gave up a lot for Lillard. Jrue Holiday made the most important defensive play in franchise history, turning the tide of the 2021 NBA Finals. Those unprotected first-round picks in 2028, 29, and 30 all have chances of being valuable. But Horst and the Bucks know they can’t sit idly by. The cost of being conservative is one of the most dominating forces the league has ever seen. No pressure or anything.
Bringing in Lillard gives Milwaukee some much-needed firepower offensively. Their offense has stalled in the postseason when the game slows down. Lillard will now stretch the floor and take some shot-creation duties and pressures away from Khris Middleton, who is looking to bounce back after a couple of down seasons. Putting Middleton in more of a CJ McCollum-esque role will benefit him — he works masterfully off the ball.
The idea of Lillard/Giannis pick-and-rolls is so scary that I don’t want to put that picture in my mind. There are still some questions with the rest of this roster, but the Bucks undoubtedly got better by adding Lillard. I do have my questions about this team’s defense, though.
Losing Holiday means the Bucks are much more exposed on the perimeter. In one summer, Milwaukee went from Jrue Holiday and Jevon Carter to Damian Lillard. A downgrade, to say the least. While Giannis and Brook Lopez will smother anything down low, relying on Khris Middleton to be your wingstopper is…far from ideal. Let’s put it like that.
Still, for the first time in his career, Dame will be able to “hide” defensively with the aid of Giannis and Lopez. Last year, the Bucks were one of the league’s top-five defenses. That will probably take a hit this season but don’t expect things to completely collapse.
Regardless, the Damian Lillard deal makes sense for the Bucks. It helps cover some of their offensive shortcomings, reassures Giannis, and makes them the favorites in the Eastern Conference. There are worse outcomes.
Grade: A-
Was Trading Ayton the Right Move for Phoenix?
After trading for Bradley Beal earlier in the summer, I assumed the Suns would rest on their laurels and enter training camp relatively drama-fee. But Mat Ishbia isn’t your typical owner. Amid the Lillard saga, the Suns found a way to continue their aggressive pursuit of a title.
It has been reported that Phoenix was carefully watching the Lillard situation unfold, planning to be a part of trades with the Bucks, Heat, or whoever else was going after Dame. Clearly, trading Deandre Ayton was of some importance to this regime.
Ayton was supposed to be one of the faces of the Suns. Instead, he became the scapegoat for the Suns’ shortcomings. Luka Doncic going two picks after him in 2018 doesn’t help matters. After a fantastic 2021 postseason, Ayton stagnated. His effort waned, and he became less and less involved offensively. Monty Williams and Ayton regularly sparred. After Kevin Durant got added, he was a footnote. And it isn’t wise to pay your footnotes $132 million.
Phoenix didn’t have much choice but to match Ayton’s massive offer sheet from the Pacers during the 2022 offseason. Such is the price for not previously extending Ayton. By trading away Ayton, the Suns now have more financial flexibility to deal with the other three max contracts on their roster.
The return, headlined by Jusuf Nurkic, for Ayton, is interesting. As a Blazers fan, I will always ponder what Nurkic could have been had he not had that horrific leg injury in 2019, the best season of his career. He hasn’t been the same player since then and has continually struggled with injuries.
Nurkic is older, slower, and less talented than Ayton. While he is much cheaper (3 years / $54 million), I don’t know if that makes up for the talent disparity. Nurkic and Drew Eubanks are innings eaters, but I doubt they’ll move the needle that much in the postseason. The prospect of Nurkic trying to stop high pick-and-rolls against teams like the Warriors is mortifying.
And, to state the obvious, the Suns are still exposed in their fight against Nikola Jokic. Trading for Nurkic or anybody, really, doesn’t change that reality. At least Nurkic will be a little more physical in the post than Ayton? That’s the only silver lining I can offer.
The other pieces the Suns added, however, make a lot more sense. Nassir Little offers size and athleticism on the wing. Grayson Allen is one of the best shooters in the league. Those two guys will surely see regular minutes in the regular season. Allen will likely be an option in crunch time with his ability to space the floor and create his own shot.
Frank Vogel’s rotation has been filled with a solid group of cheap, reliable veterans. That, along with the trio of Durant, Booker, and Beal, should be able to compete in the West. Still, no matter your opinion of him, Ayton is leaving a void behind down low. Only time will tell if that void will be consequential to Phoenix’s quest for a championship.
Grade: C+
The Miami Heat Messed Up Big Time
Oh, Miami. How the mighty have fallen. Pat Riley and the Heat arrogantly waited for months and months for the Blazers to cave. They bet everything on Portland not being able to find a better package, hoping that Joe Cronin would settle for their mediocre one. Instead, the Heat lost out on Lillard and are now in a precarious situation. It isn’t hyperbole to say things couldn’t have played out worse for Miami.
This is unusual territory for Miami. They usually get superstars who they want. From Alonzo Mourning to Lebron James, superstars like playing in South Beach. Damian Lillard was no exception. The problem was Miami didn’t have the assets to entice Portland to make Portland an offer. Or did they?
Early reports suggest that Miami’s best offer was a boatload of picks, Nikola Jovic, with Tyler Herro being rerouted to a third suitor. Portland was rightfully disinterested. Did Miami not add Jaime Jaquez Jr. or Caleb Martin? Miami may have been lacking in assets, but they had some more than that reported offer. This begs the question, was Miami not aggressive enough in their pursuit of Lillard?
That’s a damning thought for a team that desperately needed Lillard to fix their problems. Without Dame, this team’s outlook for 2024 is draconian. Gabe Vincent and Max Strus left in free agency. Miami’s offense, which ranked 25th last year, got considerably worse. With Vincent leaving, who’s going to play point guard? A 37-year-old Kyle Lowry who was benched last postseason? Tyler Herro?
Speaking of Herro, how does he feel about all of this? For months, he’s been tossed in trade rumors. This isn’t the first time this has happened. It’s only natural for him to question his place in Miami’s future. Sure, they gave him a big contract, but the front office seems very willing to trade him. Herro and Jaylen Brown should start group therapy sessions to console each other.
And now, with Jrue Holiday off the market, Miami doesn’t look like one of the juggernauts in the East anymore. Remember, this team was a few minutes from losing to the Bulls in the play-in tournament. They then benefitted from a weak playoff run to miraculously make the Finals as an eighth seed. But this is the same team that struggled mightily during the regular season. And now they got a lot worse this offseason.
Jimmy Butler is 34, and his contract will only balloon over the next few seasons. Unless Bam Adebayo turns into Hakeem Olajuwon, this team is betting on their young guys and Caleb Martin to lead them into contention. That’s not a pleasant thought.
We’ll never truly know what went wrong in the Damian Lillard negotiations. But the logistics of this organizational failure shouldn’t sit well with Heat fans. They had Lillard in the palm of their hands. He was drinking all of that Heat Culture bullshit. And then they watched him go to the Milwaukee Bucks, which indirectly hurts their chances of stealing Giannis Antetokounmpo next summer.
And now, Pat Riley has a broken, old, and weirdly constructed roster to deal with. The expectation to contend will remain, but this roster simply isn’t good enough to fulfill those aspirations. Without Damian Lillard, the Miami Heat’s future is the total opposite of South Beach.
Grade: F-
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