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Behold the Portland Trail Blazers Dream Trade

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Yes, it works. Here’s what the Blazers have to do in order to get there.

Milwaukee Bucks v Portland Trail Blazers Photo by Sam Forencich/NBAE via Getty Images

Summertime is also NBA Trade Rumor time, particularly so for teams like the Portland Trail Blazers, who seem tantalizingly close to making a breakthrough but can’t quite get there. Blazer’s Edge reader Barry makes a preemptive strike at trade rumors today, asking how realistic big moves are given Portland’s roster status, eliciting an example of a trade that would make a difference.

Guess what? We have one, and it’s a doozy.


How would you actually get a forward that we need, especially a good one? You’re the one always saying lateral trades don’t help. With the chemistry on this team I’d think that’s especially true. Do you see any hope, especially since that trade is probably going to be with CJ? Or can we get one without him? It’s easy to say it, but how do you do it?

Barry in WA

There’s one possibility I would pursue hard. You can derive permutations from there. It would work, to a lesser extent, with any relatively-expensive small forward.

The best chance the Blazers have of pulling off this kind of deal is if high-expectation Eastern Conference teams with good small forwards fall short. For that reason, every Blazers fans should instantly become a Miami Heat fan. Ideally you’d want the Heat to beat the Bucks and the Celtics to beat the Raptors in this round of the playoffs, then have the Heat cruise on to the NBA Finals. It also probably works if the Celtics make the Finals but don’t win there.

This does two things. First, Boston remains one move away from becoming the team they want to be. Second, Milwaukee and Toronto begin to wonder if they can ever win with their current set-up. Neither would be ready to blow it up entirely, but both would be staring hard at very good small forwards—Khris Middleton and Pascal Siakam—on hugely expensive contracts, wondering if those contracts were going to produce.

For purposes of our exercise, let’s narrow down to Middleton and Milwaukee. The future of Giannis Antetokounmpo is up in the air. There’s no guarantee that he stays after his contract expires in 2021. Even if he does, there’s no track record of them actually winning with the Antetokounmpo-Middleton pairing.

In this scenario, the Bucks need plausible deniability. They need significant talent now, to try and win with Giannis and convince him to stay. They can’t just blow it up, because that would be giving up on him. They probably need to try something new, though. Just as importantly, they need that talent to operate on shorter-term contracts.

For all his awesome ability, Middleton is their second banana. He’s not going to carry the team by himself should Antetokounmpo leave. But Middleton’s contract runs through 2023-24 with a player option at the end for a whopping $40.5 million. That’s justified if he’s carrying them to titles, with or without Giannis. Neither of those seems likely to happen at this point.

Meanwhile, Middleton is the exact archetype of what the Blazers need: defense, shooting range, and scoring at small forward.

Two problems:

  1. Middleton is not going to come cheap. That enormous contract should tell you how much the Bucks like him. In order for the Blazers to pry him away, the Bucks will have to lose early in the playoffs, Giannis’ future will need to be in serious doubt, and the trade offer would need to give them EVERYTHING they need to position themselves right now and in the future: current talent, future financial flexibility, future compromises.
  2. A straight CJ McCollum for Middleton swap probably doesn’t do it, even with sweeteners thrown in. CJ has plenty of talent and would probably work well with Antetokounmpo, but McCollum’s contract runs just as long as Middleton’s and is nearly as expensive. The Bucks don’t get a win in current talent, don’t get flexibility for the future, and the added assets the Blazers could throw in wouldn’t make enough difference to make up the gap.

Enter the Boston Celtics.

McCollum wouldn’t make enough difference for Milwaukee, but he sure could for the Celts.

Boston’s shooting guard, Marcus Smart, is young, talented, and plays on a very reasonable contract. He just isn’t capable of putting up the offensive numbers that CJ can. Small forward Gordon Hayward has produced well for them, but they have a glut of forwards, including Jayson Tatum and Jaylen Brown. McCollum would replace Hayward’s scoring ability, adding range at shooting guard that Smart lacks, combined in a single package at the right position. The Blazers would need to throw in Trevor Ariza to make salaries work and to give Boston back some depth at small forward.

Hayward and Smart wouldn’t be coming back to Portland. They’d go to the Bucks. They’d give Milwaukee scoring, some defense, and better backcourt depth. The talent is more spread out than it was with Middleton, but that may actually be an advantage. The Bucks need structure around Antetokounmpo—particularly veteran structure—as much as they need a sidekick.

The deal works out well financially for Milwaukee as well. Smart’s contract tops out at $15 million and ends in 2022. Hayward has a $34 million player option in 2020-21 and then he’s done. If Giannis stays and the talent mix works out, they can offer to re-sign Hayward. If Antetokounmpo leaves or Hayward doesn’t fit, they release him and have salary cap space to play with.

The Blazers would also throw in future assets to make the deal worth Milwaukee’s while. The obvious ones are Portland’s upcoming 2020 and 2022 first-round draft picks, Anfernee Simons, and Nassir Little. (The Blazers probably can’t part with Gary Trent Jr. or Zach Collins without compromising the integrity of their new starting lineup.) Portland would hope that the Bucks wanted two of those four assets, but if they had to swallow hard and give up three, they should probably do it.

Trade Summary


Gives Up: Marcus Smart, Gordon Hayward

Gets: CJ McCollum, Trevor Ariza


Gives Up: Khris Middleton, Ersan Ilyasova (for cap balancing purposes)

Gets: Marcus Smart, Gordon Hayward, Anfernee Simons or Nassir Little, Portland’s 16th pick in the 2020 NBA Draft, Portland’s 2022 first-round pick


Gives Up: CJ McCollum, Trevor Ariza, Anfernee Simons or Nassir Little, 2020 first-round pick, 2022 first-round pick

Gets: Khris Middleton, Ersan Ilyasova

The Celtics get a player to push them over the top, arguably without giving up any of their top three players (Tatum, Brown, and Kemba Walker). Losing Middleton is ouchy for the Bucks, but they get two starters now, three future assets, and the flexibility to unhitch their roster from Giannis if need be while still building around him if he stays.

This is certainly a win for Boston, probably one for Milwaukee as well in the long run. And frankly, if the Bucks didn’t see it that way, I’d ask how many more picks or young players it would take, because look what happens to Portland’s lineup after this deal.

Starters: Damian Lillard, Gary Trent Jr, Khris Middleton, Zach Collins, Jusuf Nurkic

Reserves: Rodney Hood, Ersan Ilyasova, Wenyen Gabriel, Mario Hezonja, Anfernee Simons or Nassir Little

Portland’s new starting lineup features four good-to-great defenders alongside Damian Lillard, whose personal defense now pays more dividends than it did in a starting five with McCollum and Carmelo Anthony. The Blazers feature shooting/scoring at every position in the starting lineup except power forward. It’s hard to overestimate how good that five-man unit would be.

Portland’s bench would need a little help. They still have a mid-level exception to play with, filling in big or small positions. They could chase a good backup power forward or center with that offer, filling in the reserve point guard spot with a minimum-level veteran (if Simons leaves in the trade).

Obviously all the moves Portland could make currently, including re-signing Carmelo Anthony and/or Hassan Whiteside, would still be on the table, for better or worse.

With some adjustment, this kind of deal would also work if Toronto bailed out of Pascal Siakam’s contract.

This is a Whitsitt-like move in scope, but it would transform the team in similar fashion to a pre-Whitsitt deal: the Sam Bowie-Buck Williams trade in 1989. With a balance of defense, shooting, and scoring through the lineup, Portland would move on par with the best in the West. CJ McCollum is a wonderful player, but he’d be fine challenging for a title in Boston. With Middleton as part of a new starting lineup, there’s at least a fighting chance that he’d find his old teammates waiting for him in the NBA Finals series. And what a story that would be.

Keep those questions coming to! I look forward to talking with you all summer!

—Dave ( / @DaveDeckard / @blazersedge)