RealGM

Portland Trades
Anfernee Simons to ORL
DeAndre Ayton to MIL
Shadeon Sharpe to MIL
2028 MIL Swap to MIL
2029 MIL FRP to MIL
2030 MIL Swap to MIL

Portland Receives
Chet Holmgren from OKC
Kentavious Caldwell-Pope from ORL
Kyle Kuzma from MIL

Oklahoma City Trades
Isaiah Hardenstein to MIL
Chet Holmgren to PDX
Nikola Topic to MIL
#15 to MIL
2-3 Future FRP to MIL

Oklahoma City Receives
Giannis from MIL

Milwaukee Trades
Giannis to OKC
Kyle Kuzma to PDX

Milwaukee Receives
DeAndre Ayton from PDX
Isaiah Hardenstein from OKC
Shadeon Sharpe from PDX
Nikola Topic from OKC
#15 from OKC
#16 from ORL
2028 MIL Swap from PDX
2029 MIL FRP from PDX
2030 MIL Swap from PDX
2-3 future FRP from OKC

Orlando Trades
Kentavious Caldwell-Pope to PDX
#16 to MIL

Orlando Receives
Anfernee Simons from PDX

WHY FOR PORTLAND
They pay a big price to get a unicorn in Chet who is an ideal roster fit and compliments both Deni and Clingan tremendously well. They take on Kuzma and KCP but the end result is a very solid, young starting lineup and they manage to keep pick 11 in the process.

WHY FOR OKC
If they lose G7 I can see big changes. Its been clear this playoff season that the team lacks, at least at this moment, a reliable compliment to SGA. Giannis is Giannis and adding him to SGA, Jalen and their overall depth likely makes them the easy favorite to win 1 or more titles.

WHY FOR MIL
It may be wishful thinking as a Blazers fan but here they opt to get Sharpe + their picks returned over Chet. They get a big EC in Ayton while moving off Kuzmas longer deal and Isaiah is someone that will be very 'flippable'. The pick package is pretty great - netting 5-6 FRP and 2 swaps. Topic is a nice swing as well.

WHY FOR ORL
They need that scoring guard and get one here while moving off the extra year on KCP's contract.

I think if OKC goes Giannis JWill is the centerpiece, not Chet. Chet fits too beautifully with Giannis.

I think it's a great deal for Portland (probably too good), and a very solid deal for Milwaukee.

I think it's an overpay for OKC though.

Texas Chuck wrote:I think if OKC goes Giannis JWill is the centerpiece, not Chet. Chet fits too beautifully with Giannis.

That does look ideal.

They would want to get their picks and swaps from POR and everything on the MIL roster is flaming garbage so the value would have to come from OKC.

Texas Chuck wrote:I think if OKC goes Giannis JWill is the centerpiece, not Chet. Chet fits too beautifully with Giannis.

Yeah all hypothetical but that’s how I see it too.

I think JDub would do great in Portland and fit in well as well.

Hoping OKC can get over the hump and this all just stays hypothetical.

JWill would be great to have in Portland. I'm struggling though with why Milwaukee would not just keep him? Is 4 picks too much for JWill? I don't see many OKC games so I know he's a good player; I don't know whether he is THAT good.

I would do this for Portland, but I don’t think it saves us from the treadmill. Our future would depend highly on the development of Scoot and landing a good SG with #11. Our front court would be awesome, but this leaves us with the questionable future of Scoot and practically no other guards, while not having the Bucks picks to look to for high value drafts or trades. I like Chet more than JWill, but fit wise, JWill would be much better for this team.

Isn't Homgren injured quite often? If that's the case, I'd prefer JWill.

To answer the point in the OP about this being "wishful thinking," I'm afraid that it just might be. I do think Milwaukee cuts Portland out and takes Holmgren (or Jalen Williams), and I also don't think OKC has to give up as much as you have outgoing for Giannis. So, the deal depends on OKC selling the farm for Giannis AND Milwaukee letting the biggest prize go to Portland.

Unrelated to my evaluation of the trade's merits, I like DaVoiceMaster and Myth am skeptical this saves the Blazers from mediocrity. Chet is an excellent player (and I agree he still has upside beyond the level he's already at) but a risky bet as your franchise player, which is the kind of investment Portland is making here. I'm willing to trade all that for the right piece, but I have my doubts that Chet is reliable enough to be that guy.