3 reasons the Milwaukee Bucks won’t trade for Damian Lillard

About a month ago, Damian Lillard was asked by a fan who he would pick to help him get into the playoffs and maybe the finals, his answer was Milwaukee Bucks‘ Giannis Antetokounmpo. The tweet took off and fueled a wildfire among Bucks fans about how to bring the All-Star Lillard to Milwaukee to team up with Giannis. However, unfortunately for those fans wanting Lillard in Milwaukee, it just isn’t a realistic possibility for a few reasons.

Reasons the Milwaukee Bucks won’t trade for Damian Lillard: #1 Supermax

Heading into the 2020-21 season there was a collective sigh breathed by the entire Milwaukee Bucks franchise when it was announced that Giannis Antetokounmpo was signing the supermax contract he was eligible for and remaining in Milwaukee for the foreseeable future.

However, the way the supermax extension is structured, is so that no team can have more than two players with supermax contracts, Giannis is one and Lillard would be the second. The supermax contract can take up to 35 percent of each season’s salary cap, meaning in Lillard and Giannis, the Milwaukee Bucks would have 70 percent of their salary cap spoken for. The Milwaukee Bucks ownership hasn’t been shy about going into the luxury tax but shelling out potentially $85 million for Lillard and Giannis puts the Milwaukee Bucks’ General Manager Jon Horst in a really tough position to fill out the rest of the roster with other free agents to build around the pair.

Reasons the Milwaukee Bucks won’t trade for Damian Lillard: #2 Chemistry

Tying into what constraints the salary of Damian Lillard would put on the Milwaukee Bucks, there is no possible scenario where the Bucks don’t trade either Jrue Holiday or Khris Middleton, regardless of which one it is will hurt the chemistry that has been built in the last two years with Holiday or nearly the past decade between Giannis and Khris.

Furthermore, Lillard is making $42.5 million in 2022-23, meaning if the Bucks trade Jrue the team would need to move or account for the nearly $10 million difference, possibly by including Grayson Allen, which means the Bucks would be trading two starters for one. The other possibility would be that the Bucks likely lose out on re-signing one or both of Bobby Portis and Pat Connaughton, two of the Bucks biggest bench contributors over the last few seasons. Both Portis and Connaughton are huge to the chemistry of not only the team, but the city of Milwaukee itself, Portis has endeared himself to the fans by playing hard and showing his love for the city and Pat Connaughton has contributed to the community in several ways and has rooted himself here.

If trading Khris Middleton, which would really hurt the chemistry as Khris and Giannis have been together for nearly a decade and have built an ironclad working relationship and understanding of each other’s games, the Bucks would need to account for about $5 million difference in salary, there are some bench players that could be included to make the money work out but then the next problem the Bucks would face is, who starts at point guard? Lillard and Holiday are both capable of playing off the ball, but why intentionally construct your roster that way?

Not only the chemistry of the players, but also of the play, Lillard is 5″ shorter than Middleton, and while Middleton is not known for his defense, there is something to speak for his length that does contribute on the defensive end. Not that I don’t believe Lillard is capable of being the second option to Giannis Antetokounmpo, but it is a role that Khris Middleton has adapted to and embraced as a Milwaukee Buck.

Reasons the Milwaukee Bucks won’t trade for Damian Lillard: #3 Trading a 31 year old for a 31 year old benefits no one.

As I mentioned during the chemistry reason, Jrue Holiday and Damian Lillard play the same position. While there is absolutely no doubt that Damian Lillard is a much better offensive player, the defensive side of the game tips in favor of Holiday. Ultimately, this deal is somewhat of a lateral move for both teams when considering the boost at point guard the Bucks would get versus the opportunity cost of who they could lose by taking on nearly $10 million of additional salary and sending out another first round draft pick, leaving the Bucks in an extremely difficult position when trying to replenish depth.

Looking through the eyes of the Portland Trail Blazers, trading a franchise cornerstone for a player that plays the same position, is the same age and isn’t nearly as flashy to watch seems like a way to ensure that less fans come to watch games. While the $10 million difference in salary offers some opportunity, the Blazers simply have extremely little incentive to trade for a player the same age as the one they would receive. It is far more likely that the Blazers would be looking for a large package of picks and players, similar to what the Los Angeles Lakers paid for Anthony Davis or Russell Westbrook, to kick off a full scale rebuild, trading for 31 year old Jrue Holiday, Grayson Allen, the 24th pick and some second rounders isn’t going to be enough to entice the Trail Blazers to send Lillard to Milwaukee.

The idea of Damian Lillard and Giannis Antetokounmpo together in Milwaukee is one that is fun on paper but ultimately unrealistic in the real world outside of a video game.