Ranking the 6 best trades of the Milwaukee Bucks’ Jon Horst era

No. 1 – The out of nowhere Damian Lillard trade

It seemed like a huge long shot that any trade would dethrone the Jrue Holiday deal anytime soon, but that all changed in the blink of an eye on September 27. Out of nowhere, the Milwaukee Bucks acquired Damian Lillard in a three-team deal with the Portland Trail Blazers and Phoenix Suns, and they immediately were the talk of the entire NBA landscape.

In the deal, the Bucks shipped out Jrue Holiday, Grayson Allen, a 2029 first rounder, and two future pick swaps in 2028 and 2030 in exchange for Lillard. Holiday landed in Portland alongside a trio of draft picks, Deandre Ayton and Toumani Camara. Allen will now go to Phoenix with Keon Johnson, Nassir Little, and Jusuf Nurkic.

While it’s tough to see Holiday go, especially given everything he meant to this team on and off of the court, Lillard is an upgrade at the point guard position. Allen’s absence means the Bucks will be starting a new two guard this coming season, but it seemed inevitable that he would be traded at some point this year. Who could have guessed it would be in a deal for Lillard?

Lillard is a tremendous addition for the Bucks, immediately giving them more star power – he was named one of the 75 best NBA players ever in 2021. Alongside Giannis Antetokounmpo, Lillard is a perfect partner, as he can stretch the floor way beyond the arc to allow the Greek Freak to operate down low. These two may instantly become one of the most lethal offensive duos in the league.

Speaking of Giannis, this news certainly showed how seriously the front office took his comments about wanting to make sure everyone was on the same page before signing a contract extension. Though Giannis will likely wait to sign an extension if he plans to, as he would make more money, this deal will likely be similar to the Holiday one in the sense that it makes him very happy.

Understandably so, most of the talk involving this deal has revolved around the fit between Lillard and Giannis. However, adding Lillard will also benefit Khris Middleton, who will now become a third option on offense, meaning he will get lesser defenders compared to what Lillard and Giannis will receive. That should help fuel his success on that side of the ball this coming season.

Lillard is yet to suit up for the Milwaukee Bucks, but on the surface, there is no doubt that this is the greatest trade Horst has made in his tenure, as it pairs together two superstars and puts the team in a position for years to come. The new NBA season cannot come soon enough.

Stay tuned for more Milwaukee Bucks analysis ahead of the upcoming 2023-24 NBA season.