Milwaukee Bucks season preview: Where Damian Lillard, Adrian Griffin, and the new-look Bucks stand going into the 2023-24 season

By: Noah Nelson 10/6/2023

‘How do we win an NBA Championship?’ is the question on every GM’s mind in the offseason.

For the Milwaukee Bucks, that question has never been more important.

Following two consecutive years with disappointing playoff losses, Giannis Antetokounmpo voiced his concerns about his future with the team, and with the sudden removal of Coach Mike Budenholzer, the stakes have never been higher. Immense pressure was placed on GM Jon Horst to solidify a championship-caliber roster.

With Damian Lillard available via trade, Horst went all in on securing Giannis’ future and beat out teams like the Miami Heat, Toronto Raptors, and Brooklyn Nets in bagging the seven time All Star.

With athletic rookies, six new coaches, higher energy on the bench and of course Damian Lillard, the Bucks are clearly attempting to transcend the Budenholzer era and usher in a new dynasty in Milwaukee.

Signings, Re-signings, and ‘The Trade’

‘Dame Time’ in the 414

Jon Horst has been Milwaukee’s magician for the past 10 years, and he may have just performed his greatest trick.  

Needing little more than draft picks and fringe stars, Horst has imported three iterations of star point guards to Milwaukee: Eric Bledsoe in 2017, Jrue Holiday in 2020, and Damian Lillard in 2023.

On July 1, 2023, Damian Lillard requested an exclusive trade to the Miami Heat.

On Sept. 27, he was traded to the dark horse Milwaukee Bucks.

After months of silence from Milwaukee’s camp and with little indication of their interest in Lillard, the Bucks somehow acquired the 33-year-old superstar for a ‘measly’ package of Jrue Holiday, Grayson Allen and some prospects who are still in middle school (2029 first round pick and the 2028, 2030 first round pick swaps). Portland received more in compensation, bringing in the Suns as a third team partner, acquiring Deandre Ayton before eventually offloading Holiday to the Celtics.

Of course, the loss of Jrue Holiday is painful on the defensive end and what he brought to this team’s culture will be difficult to replace. He was crucial to the Bucks 2021 run and fans should be forever grateful for what he brought to the city.

So, what exactly does Lillard bring to Milwaukee? ‘Dame D.O.L.L.A’ adds another dimension to this Milwaukee offense and his three-level scoring ability will likely open the floor for Giannis and co. to find more open looks. The pick and roll game with Giannis will be virtually unstoppable and the team is likely to be a gear or two faster in the half court.

More importantly, he’s one of the most recognizable big-moment players in the league. With the Trailblazers, he was a part of four playoff series wins. In two of them, he hit the series winning shot. Lillard embraces the last two minutes of games and when paired with Giannis and Middleton, the Bucks will have three proven clutch playoff scorers. Again, no disrespect towards Jrue Holiday, but he shot 40% and 36% in the last two playoff series losses for Milwaukee.

Essentially, the offense just leveled up twice and where the defense may struggle, the Bucks accommodate for with one of the best fitting duos in league history.

Re-signings – Starters

Khris Middleton and Brook Lopez were the two biggest concerns for Milwaukee on the player retention side of this offseason, both on expiring deals with reported interest around the league. Losing Lopez would be a gut shot for the Bucks, so the team went all in on the aging center, offering a two-year $48 million contract, beating out the Rockets similar bid. Khris Middleton’s free agency was short lived as well. He agreed to a three-year deal worth up to $102 million and underwent a successful surgery on his nagging right knee injury. With the core returning, focus transferred to the bench, which, after losing 9 part-time contributors, needed intense renovations. 

Re-signings – Bench

The Bucks biggest move of the 2022-23 trade deadline was for 32-year-old Jae Crowder, presumably for his playoff presence, yet he only played 30 playoff minutes in the five-game loss to Miami. He was reportedly, “confused as to why [he] was brought here,” however, he re-signed in the offseason for 1 year $3.19 million in the weeks following Budenholzer’s removal. He seemingly believes in this team and will likely have a greater role next season under Griffin’s adapted leadership strategies.

AJ Green is the other bench re-signing, agreeing to 3 years, $6.32 million. He’s a shooter and he eclipsed 40% from three in his limited minutes last season, which in the modern NBA can keep a player on the court and pay them well for it (Duncan Robinson $90 million). The depth of this Milwaukee team does limit Green’s time, however, and he will likely see mostly blowout minutes or early second-half small ball time, though he could work his way up in the rotation.

The Energy Guys

In the 2019-20 season, the Bucks dove headfirst into creating a familial environment, becoming the only NBA team in history to have two sets of brothers on their team at the same time, signing Robin Lopez to a 1-year deal and Thanasis Antetokounmpo to a multi-year minimum contract.

Now, following three years on three different teams, Brook Lopez’s younger brother (by one minute) is back in Milwaukee. While neither of these guys is good enough to play for this Bucks team consistently, they make their teammates better and create an environment that conjures winning, which one could argue is more valuable than what another veteran minimum guy might provide.

Remember Thanasis’s play against Brooklyn? How about WrestleMania pregame? The front office knows that Thanasis and Robin won’t give you 20 points per game, but they are essential to the team environment and culture necessary to reach, and win, the NBA Finals.

Fresh Meat – Malik Beasley & Cameron Payne

What if there was a way that the Bucks could replace Joe Ingles for someone nine years younger for a fraction of the cost who just made the most bench threes a season ago? One would expect Jon Horst to jump all over that.

And he did, signing Malik Beasley to a 1 year/$2.7 million deal. By bringing in a sharpshooter like Beasley and doing it on a veteran minimum, the Bucks replace the older, slower Ingles for a volume bench scorer who’s never had completely reconstructed knees. But there’s a slight catch. Beasley went to jail in 2020 for waving a rifle at strangers in his neighborhood. His off-court offenses may make GMs wary, but the Jazz and the Lakers have both given Beasley opportunities since the incident, and there are signs of personal development that can hopefully translate to Milwaukee on a team friendly deal.

The backup guard spot has been filled as well with Jae Crowder’s former teammate Cameron Payne. Payne is coming in as a double-digit scorer and is likely to provide a spark from the bench, but if not, he at least provides another option for the Bucks at the guard. The backup guard spot was a glaring weakness for Milwaukee this summer, and Payne could be the right player to finalize this roster.

As the last contracted player in the 14-player team, he brings the Bucks payroll to $183.68 million and ups the team’s luxury tax to almost $58 million.

Young Bucks

Gone are the days of the high-IQ, unathletic, low-ceiling, second rounders that fans have become so accustomed to during the Budenholzer era.

Unfortunately, due to investments in the present, the team is essentially bone dry when it comes to future first rounders, but the team has had success in the second round in the past. While Brogdon clearly overachieved, teams find value in round two every year, and maybe it’s Milwaukee’s time again.

Andre Jackson Jr. (Pick No. 36)

Despite averaging a ‘measly’ 6.7 points, 6.2 rebounds, and 4.7 assists last season in college, the Bucks first pick in 2023, Andre Jackson Jr., impacted winning beyond the stat sheet, helping propel the UConn Huskies to their fifth national championship.

UConn’s coach Dan Hurley praised him as a “tone setter,” and said that Jackson, “genuinely cares more about our success than his own production.” His maturity is not the only reason why Milwaukee traded up for him: he is an NBA-ready talent with a high basketball IQ and elite size/speed. Jackson’s 39 ½-inch vertical and 3.14 second three-quarter sprint both ranked in the top five in the draft combine, and he was considered ‘A Dunker From The Gods’ during his time in high school at The Albany Academy. While he still has work to do offensively, mainly with his shooting mechanics, Jackson hangs his hat on the defensive end.

Here’s the skinny on Jackson: he’s a superb athlete with a seemingly endless motor – a true immediate impact guy for this Bucks team. Think Thanasis Antetokounmpo’s energy but in a more coordinated, pass first guard who can both find and throw down an alley-oop in transition.

Chris Livingston (Pick No. 58)

The Bucks second of two picks was another NBA-ready athlete and the final overall pick in the 2023 draft, Chris Livingston.

Note: NBA-ready athlete. Livingston is still underdeveloped skill-wise and likely a developmental piece at this stage. Widely considered the best Akron prospect since Lebron, Livingston underperformed at Kentucky as a freshman in 2022-23, and though he came in as a projected lottery pick, he seriously considered returning to college to boost his draft stock. During the buildup to the draft, Livingston cancelled his last seven pre-draft workouts, fueling belief that he had a guaranteed deal lined up later in the draft. Of course, he did have a deal with the Bucks: a four-year, $7.7 million deal which is the most guaranteed money of any final pick in the draft.

Coaching Overhaul

Head Coach Adrian Griffin

“They’ll never know how much you know, until they know how much you care.” 

  • Adrian Griffin, June 6, 2023, in his first official press conference as Bucks Head Coach

In the offseason following the loss to the eight seed Heat, the Milwaukee Bucks parted ways with Mike Budenholzer in favor of Raptors Lead Assistant Adrian Griffin. A former NBA player himself, he understands how to gain a player’s trust and connect with his team. Since the NBA-ABA merger, only five first-year coaches have won the finals, however, in the last eight years there have been three: Steve Kerr in 2015, Tyronn Lue in 2016, and most recently Nick Nurse in 2019 (Griffin was lead assistant for Nurse at the time). The Bucks, of course, hope Griffin can continue this trend, but the responsibility does not rest solely on his shoulders – more than half of the game-night coaching staff have been replaced.

The Rest of the Staff

In total, six new coaches were hired for the Bucks, but fans may recognize some of these ‘new hires’ from their past time spend with Milwaukee. Assistants Terry Stotts and Joe Prunty have both acted as head coach for the team – Stotts from 2005-’07 and Prunty as the interim coach following the firing of Jason Kidd. Coincidentally, Stotts coached Damian Lillard until 2021 which may have tipped the needle in his willingness to come to Milwaukee.

In addition, two members of the Raptors organization are following Griffin: Patrick Mutombo and Nate Mitchell. Rounding out the new hires is D.J. Bakker who last coached for Detroit’s G-League affiliate, the Motor City Cruise, in 2023.

Returning on the coaching staff are former Bucks All-Star Vin Baker and Josh Oppenheimer, who’s on his second stint with the Bucks and has also coached Giannis on the Greek national team (2022). In a historic move, Sidney Dobner is being promoted from head video coordinator and will be the first female assistant coach in franchise history, which Griffin highlighted as his, “best hire”.

The preseason starts on October 8th, so fans will be able to see this new Bucks team in action very soon. On paper, they’re cohesive. They’re experienced. They want to win, and they want to win now. Is Milwaukee ready for another parade? 82 games and the playoffs will prove if this ‘rebuild’ was effective, all fans can do now is wait to see.

Quick Hits – Names to Know

Lindell Wiggington – Two-way contract, your new favorite G-League microwave, Iowa State alumni

TyTy Washington – Two-way contract, 2022 first-round pick, another Kentucky guy

Omari Moore – Two-way contract,NBA ready frame, project prospect

Jazian Gortman – Training camp contract, OTE League alumni, elite talent

Tacko Fall – 7’6”, worst free throw form ever(?), signed with the Nanjing Monkey Kings

Drew Timme – Gonzaga legend, skilled but undersized, seems like he’ll stay in the G-League

Jimmy Haslam – Browns owner w/ minority stake (25%) in MKE, proven he’s willing to spend

Sidney Dobner – Dislikes glass ceilings, former college baller, more than just a diversity hire

Marjon Beauchamp – 83(!!!) points in Crawsover Pro-Am, defensive wing with energy, second year jump incoming?

Jrue Holiday – Bucks legend, less than glorious exit, Celtics revenge series potential

Giannis Antetokounmpo – Got his coach, team built around him, two years left on his deal, ready to win again