Since taking over as the general manager of the Milwaukee Bucks in June 2017, Jon Horst has made his share of notable moves.
Not every move has hit, but the 2019 Executive of the Year has done his part to consistently put this team in a position to win it all, having finally gotten over the hump in 2021. A few of Horst’s moves during that 2020-21 season will certainly make this list. With that said, let us rank the six best trades by Jon Horst since he took over in 2017.
No. 6 – The George Hill trade
To start the 2018-19 NBA season, the Milwaukee Bucks were rolling. Giannis Antetokounmpo was playing at an MVP level, and in his first year as head coach, Mike Budenholzer helped the Bucks up their stature on the defensive end. Yet, Jon Horst felt like this team could use more, having made a three-team trade with the Cleveland Cavaliers and Washington Wizards for more point guard help.
In the deal, the Bucks traded Matthew Dellavedova, John Henson, and a 2022 first-round pick to the Cavaliers while receiving George Hill, Jason Smith, a 2021 second-round pick, and cash to the Bucks. Cleveland traded Sam Dekker to Washington for a second rounder in the deal. There really were not any major “losers” in this particular deal, but it proved to be a good move for the Bucks.
Hill didn’t put up crazy numbers in the regular season upon arriving in Milwaukee, but he proved to be a solid addition to this bench unit. However, once the playoffs began, Hill’s importance was off the charts. In 15 games during the 2019 NBA Playoffs, Hill averaged 11.5 points and 2.8 assists per game while shooting 53.4 percent from the floor and 41.7 percent from deep. He was great.
The Bucks fell short in the Eastern Conference Finals that season, but Hill was not one of the big reasons why. In fact, he was one of the players who actually rose to the occasion. The Hill trade was one of the reasons Horst won Executive of the Year in the months that followed, so it made sense for the team to re-sign him on a new deal that off-season.
Hill was even better for the Bucks in 2019-20. He had an incredible regular season showing, as he averaged 9.4 points while shooting extraordinarily, having hit 51.6 percent of his field goals and an NBA-leading 46 percent of his threes. While his shooting percentages regressed, Hill was still one of the more reliable Milwaukee Bucks in that playoff run in the bubble that ended in round two.
Despite his strong play, Hill was included in a trade that off-season that will appear much higher on this list. During his first stint with the Bucks, Hill was a solid rotational player who was worth what the team gave up to get him. Of course, he came back for a second stint, but that does not have anything to do with this 2018 trade. To this day, that trade was a great move.
No. 5 – The Grayson Allen trade
For years, the Milwaukee Bucks constantly cycled through names at the starting shooting guard position. Donte DiVincenzo had been the starter for all of 2020-21 before an ankle injury knocked him out of the NBA Playoffs. As DiVincenzo recovered, the Bucks swung a trade for another young contender to take the reigns at the starting two guard, Grayson Allen.
The Bucks acquired Allen and cash from the Memphis Grizzlies in exchange for guard Sam Merrill and two second round picks. It was immediately viewed as a nice move for the Bucks due to their need for depth in DiVincenzo’s absence, which carried over deep into the season. Allen was an immediate upgrade over Merrill, who scarcely played in his rookie season the year prior.
Shortly after getting off the plane, Allen became Milwaukee’s starting two-guard. Playing a major role as a full-time starter for the first time in his career, Allen took advantage of the opportunity and put up the best numbers of his NBA tenure in several categories. He primarily made his mark as an outside shooter, hitting 40.4 percent of his triples over the past two years with the Bucks.
To be clear, the Allen acquisition wasn’t a home run for Milwaukee, as the guard has had his share of struggles, particularly in the 2022 Eastern Conference Semifinals. However, it’s hard to deny how good of a move this was for the Bucks, having flipped a second round pick who was never going to see prominent time into a full-time starting shooting guard.
The Allen trade recently just helped the Bucks land another player, and that trade will be featured near the top of this list.
No. 4 – The Eric Bledsoe trade
Entering the 2017-18 NBA season, it was clear that the Milwaukee Bucks were worth monitoring as an up-and-coming team. Giannis Antetkounmpo was coming off his first All-Star selection, and Khris Middleton was coming into his own as a second option. Yet, it felt like this team needed just a bit more to truly take the leap, and that came in the form of the Eric Bledsoe trade.
Bledsoe made it clear that he wanted a trade away from the Phoenix Suns, and the Bucks obliged in early November by sending Greg Monroe, a 2018 second round pick, and a 2020 first round pick in exchange for his services. This was exactly the kind of trade the Milwaukee Bucks needed at the time, giving them the best point guard they had in a long time.
The guard immediately saw a prominent role with the Bucks, having started in all 71 games that regular season. This continued over the next two seasons, as Bledsoe was a key part of the Bucks becoming one of the league’s top contenders. He became a stellar defender at the guard position, having earned back-to-back All-Defensive nods in 2019 and 2020.
The biggest stain on Bledose’s time with the Bucks was his playoff struggles. For three years, he could never live up to the task of helping Milwaukee succeed in the postseason, having struggled year after year. It was tough to watch, and after falling short against the Heat in 2020, it was clear that the Bucks had to go in another direction, having traded away Bledsoe for another point guard.
Despite Bledose’s playoff struggles, this was a good move for the Bucks. It showed that they were ready to contend, and they formed a nice Big 3 with Bledsoe, Antetokounmpo, and Middleton. The guard was the perfect complementary piece next to those two and helped them out tremendously as they earned All-Star selections, MVPs, Defensive Player of the Year Awards, and more.
Had they not brought in Eric Bledsoe, who knows if Milwaukee’s ascension to title contention would have happened as it did. The trade itself was beyond reasonable at the time.
No. 3 – The P.J. Tucker (and MarJon Beauchamp) trade
It was no secret that the Milwaukee Bucks were looking for defensive reinforcements during the 2020-21 season. They were rumored to be interested in both Robert Covington and P.J. Tucker of the Houston Rockets. Milwaukee’s interest in Tucker never faded, and before the trade deadline in March, they finally got the guy they wanted to fortify their defense.
The Bucks traded away D.J. Augustin, D.J. Wilson, a 2021 first-rounder, and a 2023 first-rounder for P.J. Tucker, Rodions Kurucs, and a 2022 first-round pick. It was an excellent deal for the Bucks. Augustin was struggling, and this helped the Bucks get out of his hefty contract. Wilson was out of the rotation and needed a fresh start. Shuffling around the picks made sense for both teams.
Shortly after arriving, Tucker dealt with some injuries and missed some time. The Bucks were very cautious, knowing they needed him for the postseason. That quickly proved to be the case after he was made a full-time starter once Donte DiVincenzo went down early in the playoffs. For the rest of the 2021 NBA Playoffs, Tucker gave the Bucks a boost they had been lacking in previous years.
Throughout that playoff run, Tucker played every game like it would be his last. He played the part of the defensive stalwart that Milwaukee needed, oftentimes taking on the most difficult tasks on that end. The primary example of this was in round two vs. Kevin Durant and the Brooklyn Nets. Durant got his points, but Tucker made life as difficult as possible for him on every possession.
Though Tucker was most known for defending Durant, his best playoff effort typically came when he was matched up with guards such as Trae Young and Chris Paul. Against guards, Tucker held guards to 38-of-97 shooting (39.2 percent) while forcing 17 turnovers. This was huge for the Bucks, as it let their other defenders focus on their offensive production or other defensive tasks.
Tucker’s contributions, though not plentiful on the stat sheet, were one of the many reasons as to why the Bucks were champions that season. Despite how impactful he was, the Bucks let Tucker go in free agency as the forward flew to Miami. It’s a decision that is still heavily discussed among Milwaukee Bucks fans to this day, and it won’t stop anytime soon.
Getting Tucker alone would have made this one of Horst’s best moves, but they also swapped a future first-rounder, which they used to select MarJon Beauchamp. Though he didn’t play much during his rookie season, the swingman seems poised to take a leap in year two and be a big part of the team’s success. If so, this trade could get even better for the Milwaukee Bucks.
No. 2 – The Jrue Holiday trade
After three brutal playoff exits, it was clear that the Milwaukee Bucks needed to move on from Eric Bledsoe, who struggled in all of them. The Bucks were heavily shopping the guard around the league in hopes of getting an upgrade. For a while, it seemed like the team was stuck, but that all changed on a historic November night in 2020 when a blockbuster four-team deal went down.
On November 23, the Bucks traded George Hill to the OKC Thunder while sending Bledsoe, three future first round picks, and two pick swaps to the New Orleans Pelicans for Jrue Holiday and the draft rights to Sam Merill in a deal that also included the Denver Nuggets. It was a major move for the Milwaukee Bucks, who paid a hefty price for an upgrade in the backcourt.
Yet, in addition to simply getting Holiday, this deal was also about assuring Giannis that the team would do everything possible to win a title. Indeed, the Greek Freak thought it was enough, as he inked a massive five-year extension shortly after that move went down. Sure, the Bucks gave up a ton for Holiday, but Antetokounmpo’s extension and what came soon after made it all worth it.
Upon arriving, Holiday instantly clicked with his new teammates. He provided excellent defense, which earned him a First Team All-Defensive nod that season. He wasn’t too shabby on offense either, serving as the perfect third piece next to Antetokounmpo and Middleton. Yet, the true test would be the NBA Playoffs, where history happened.
In his first playoff run with the Bucks, Holiday had his share of ups and downs with the Bucks, but he always came through when it mattered. Whether he made timely buckets or one of the most iconic defensive plays in NBA Finals history in Game 5 versus Phoenix, the guard was a key cog in helping the Bucks win it all in 2021.
Over the past two seasons, there’s no denying that Holiday has had his share of playoff struggles. Still, even then, the team would make this trade again 10 times out of 10. Holiday has been vital in making this iteration of the Bucks contenders at a time when the franchise desperately needed an instant shot in the arm. He was the best trade acquisition in recent memory up until very recently.
Though he’s no longer in town, he’ll still be remembered as the ultimate needle mover in 2020-21.
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.