Bucks Talk: Trying to get the money and picks right for a massive NBA deal
The rumor mill continues to swirl around Dame Lillard, arguably one of the top ten players in the NBA and where he might end up. It appears the Trail Blazers are about ready to go through a full-rebuild. Milwaukee is still wondering, “what in the world happened to our season?” Pairing Giannis and Dame together is a Bucks fan’s dream.
Both Lillard and Giannis have been able to “flirt” a little through social media. And grabbing Lillard through a trade, pairing him with Antetokounmpo and Jrue Holiday makes this team instantly better. Maybe even Championship better!
But what would it take? Any team can make a “bad deal”, and teams not in the playoffs might be eager to make a “big deal”. But what deal would make sense? What possible trade scenarios could work best for the Bucks and best for the Blazers. We will go in order from option #1 (great for the Bucks) to option #3 (maybe not so great). This exercise is to see what it would take to get Damian Lillard together with Giannis.

Related: 2 Reasons the Bucks won’t hire Nick Nurse: And one reason they should
Option #1- Just Middleton and Connaughton
This one makes the most sense if Portland would go for it. You’d have to believe Middleton could be a placeholder-type “face of the franchise” while reuniting with P.C. would help your team compete now.
It is unlikely that a rebuilding team would go for a deal that did not include any draft picks. Unfortunately, for the Bucks, they don’t have much. To sweeten the deal they could add in this year’s second round pick. (They don’t have any picks in the 2024 draft.) The Bucks could even add in a later first round pick.

Mjs Bucks19 11 Jpg Bucks19
Syndication Journal Sentinel
Option #2- The Three Team Move
Hello Houston!
Houston only had 20 wins last year. They are in the running for prized prospect Victor Wembanyama. And they have both picks and cap space. Plus they have some interesting young players. Houston may like to add a pick and Grayson Allen to their mix.
The Bucks have veteran talent.
The Blazers just want to get better.
In this “fun”, also not likely trade scenario, (5% chance) the Blazers pick up Houston’s 2024 1st, the Bucks second round pick this year, the Bucks second round pick in 2024 and Grayson Allen.
They would give up Ty Ty Washington (to Mil). They would also send athletic forward Jae’Sean Tate to the Blazers. Portland would still grab Khris Middleton. The Blazers would also grab the Bucks 1st round picks in 2028 and 2029 and a pick swap in 2024 with Houston.
The Bucks would receive Damian Lillard along with Ty Ty Washington.
This deal is interesting on its face because it would be Houston starting to make moves now to try to make the playoffs. It also gets Portland Khris Middleton and some picks.

Related: Bucks Love/Hate Trade Rumors
Option #3- Let’s really make it a party (4 Team Swap)
This is why we have the D. Rose picture above; in this scenario you’d have to find the New York Knicks really wanting to move off that contract.
In the NBA, teams make massive deals all the time involving lots of players. This deal would involve the Milwaukee Bucks, Oklahoma City Thunder, San Antonio Spurs and New York Knicks.
The easiest way to think of this is like this: Milwaukee has no picks but has some players, the Knicks have a few picks and little salary room, Portland has younger assets and picks and OKC has a TON of picks.
- The Bucks Receive Damian Lillard and OKC’s 2029 1st round pick
- The Knicks Receive Khris Middleton and Aaron Wiggins (OKC). (The money here gets tight.)
- Oklahoma City Receives Josh Hart, Evan Fournier, the Bucks 2024 second round pick and Jabari Walker
- Portland Receives Josh Giddey, Derrick Rose and Grayson Allen and OKC’s 2023 least favorable 1st round pick and a 2025 pick.
WOW! That is a lot! But it upgrades all four teams. The money works (especially if the Knicks can get Khris to spread out salary over a long term deal) and Portland gets three nice veteran pieces along with some picks and expiring deals. If OKC is high on Josh Hart it kinda makes sense (they do give up a lot in this scenario.) But hey, it’s “fantasy basketball here.”
What do you think? Leave a comment below.
For the Bucks, this would be the ultimate “all-in”. You’d have to hope, above all hopes, that Damian Lillard, paired with Giannis, would take Milwaukee to another NBA Championship.
Follow me on Twitter at @authorrudylb and check out my other writings at www.rudylb.com. Check out the cool I-Heart Radio Podcast Gyro Step Podcast here. Follow us at @WiSportsHeroics for all things Wisconsin sports. Also, check out our merch store for some amazing WSH merchandise!