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The Milwaukee Bucks are in the midst of their first NBA Finals appearance in 37 years and are gunning for their first NBA championship in four decades. As it stands, this is already a tremendous playoff run for the Bucks. However, seeing it end without lifting the Larry O'Brien will definitely be disappointing.
In case they do not win this year's NBA championship, the Bucks may feel like they need just a little bit more to finally push them over the top. Perhaps Portland Trail Blazers superstar Damian Lillard will be the solution to help Milwaukee win its first title since 1971.
Unfortunately for Milwaukee, the only way they can get Lillard is through trade and they have close to zero assets that will entice the Blazers to even listening to them on the phone. They already emptied their cupboard of draft capital to acquire Jrue Holiday last year. With that, a Lillard trade involving just Milwaukee and Portland is just impossible to imagine. Thus, the Bucks may need to tap into a third team in order to bring in the All-NBA point guard.
Perhaps Milwaukee may find that third team in the Philadelphia 76ers. With that, the structure of the deal would probably begin with Lillard, of course, going to the Bucks for a chance to win a championship with Giannis Antetokounmpo. The Sixers would send Ben Simmons to the Blazers, while Milwaukee ships Khris Middleton to Philly.
There will certainly need to be additional pieces in this particular three-way deal. Perhaps the Bucks will also need to give up promising guard Donte DiVincenzo in the trade, while also giving away whatever is left of their draft picks, if there are any.
From the looks of it, perhaps the only way this deal takes place is if Lillard expresses that he wants out of Portland and he explicitly tells the Blazers front office that he wants to head to Milwaukee to give him the best chance of winning a title. The Blazers will probably honor the 30-year old's wishes as a way of showing appreciation for everything he has done for the franchise over the nine years.
With this trade, the Bucks will now banner a big three of Giannis Antetokounmpo, Damian Lillard, and Jrue Holiday. On paper, that trio should match that of the healthy version of the Brooklyn Nets big three of Kevin Durant, James Harden, and Kyrie Irving.
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Replacing Middleton with Lillard undoubtedly gives Milwaukee a massive upgrade. While Middleton is very much capable of being one of their primary playmakers, Lillard is one of the best scorers in the NBA and is simply on higher level than the 6-foot-7 wing. In addition, Milwaukee will benefit from Dame Time with Lillard's elite clutch shot making down the stretch of close games.
Lillard, however, would be a downgrade for them defensively. Nonetheless, Milwaukee has a strong team defense and Holiday's presence on the perimeter should be more than enough to cover the 6-time All-Star's deficiencies on that end of the floor.
Philly would probably consider doing this deal as they probably wouldn't need to give up much else other than Simmons. Middleton fits their need of bringing in a primary playmaker that can create his own shot. The 2-time All-Star is a capable scorer that the Sixers can go to whenever they need a bucket and he should instantly have the ball in his hands in close games. Middleton also would not be massive downgrade defensively for the Sixers given his good size and sharp instincts on that side of the ball.
Meanwhile, the Blazers build their team around a promising young star like Simmons and make him the new face of the franchise. The Aussie undoubtedly has his strengths as an absolute dynamo in the open floor, an elite playmaker, and an All-NBA defender. However, the 24-year old's lack of shooting makes him somewhat of a semi-project that Portland could develop as they move towards a rebuild.
Overall, the three teams involved in this deal could talk themselves into considering pulling the trigger. The Bucks are obviously the huge winner in this trade as they acquire arguably one of the top 10 players in the league to pair with a 2-time MVP and arguably the best perimeter defender in the NBA. This would instantly make them a top-2 favorite in the East once again.
Meanwhile, Philly may be looking for a change, especially after another disappointing run from their star point guard. Finally, Portland could finally hit the reset button and bring in someone who they can give the keys to the franchise.
