After the Milwaukee Bucks hoisted the Larry O'Brien Trophy in 2021, many thought that they were in a position to earn a few more in the years that followed.
For one reason or another, they haven't, although it hasn't been for a lack of trying. General manager Jon Horst has consistently been working the phones over the past several offseasons, making the moves he believed gave this team the best shot to win it all. Some have been good, some have been bad and some have been somewhere right in the middle. No one can question the effort.
With that said, let us look at Milwaukee's major moves over the past several offseasons since winning it all and rank them by year.
No. 4 - 2021 offseason
Fresh off the championship, the Milwaukee Bucks needed Jon Horst to adequately stack the deck to help this team defend its title the following year. What followed was certainly a mixed result, with the former Executive of the Year making two strong moves and then a handful of them that looked good on paper but never panned out to Milwaukee's liking.
The good: Re-signing Bobby Portis, trading for Grayson Allen
After helping Milwaukee secure the title, Bobby Portis was destined to opt out of his deal, and many thought he'd depart. However, taking a sizeable discount, he returned to the Bucks on a two-year deal worth just under $9 million. It was an excellent move to help retain a key cog in the second unit on an incredibly team-friendly deal.
With the injured Donte DiVincenzo set to miss time, the Bucks made a trade for Grayson Allen to add shooting guard depth, giving up Sam Merrill, who scarcely played in his rookie season, and a pair of second-round picks. Allen went on to play some of the best basketball of his career in Milwaukee as he started for a good chunk of his tenure.
The bad/mixed: Signing Rodney Hood, signing Semi Ojeleye, signing George Hill, letting P.J. Tucker walk, drafting Sandro Mamukelashvili, drafting Georgios Kalaitzakis
Outside of those two moves, everything else was a swing and a miss for the Milwaukee Bucks. While both were signed on team-friendly deals, Rodney Hood and Semi Ojeleye never found their footing and didn't even make it to the trade deadline. Milwaukee used a draft pick on Kalaitzakis but later waived him. Mamukelashvili showed potential but never panned out, eventually being cut.
The George Hill signing looked like an easy base hit for Milwaukee. With their backcourt point guard rotation all over the place during the title run, the Bucks brought in a familiar face to guide the bench brigade. However, Hill was not the same player he was during his first stint in Milwaukee, having taken several steps back, eventually being used as a trade chip.
Yet, even with all of those moves, the worst was letting P.J. Tucker walk after he played such a crucial role in them winning the title. For years, they have been searching for a player who can fill his shoes - let's hope Taurean Prince can do so this year - when they could have just given him his money. The lack of a reliable wing defender has come back to hurt this team again and again.
No. 3 - 2022 offseason
After falling short against the Boston Celtics in the NBA Playoffs, the Milwaukee Bucks opted not to shake things up too drastically. The plan was to run it back with a few smaller modifications around the roster's edges, and the result has been a mixed bag to this point.
The good: Re-signing Bobby Portis, signing AJ Green to a two-way contract, re-signing Jevon Carter, re-signing Wesley Matthews
With Portis once again testing free agency, the Bucks locked him up long-term by handing him a deal worth over $48 million to reward him for his series of team-friendly deals. Locking him in was crucial. Milwaukee also retained two solid defenders in Mathews and Carter, who both carved out roles for themselves after coming aboard mid-season in 2021-22 and would be needed the following year.
Snagging AJ Green out of the undrafted pool post-draft looks like a win for the Milwaukee Bucks. Green, who is about to enter his third season, showed last year that he could help this team with his sweet shooting and defense, and if he can indeed leap into the rotation, he'd be an incredible hidden gem find for this franchise on a cheap contract.
The bad/mixed: Drafting MarJon Beauchamp, re-signing Serge Ibaka, signing Joe Ingles, re-signing Jordan Nwora
Unlike the last section, there are no flat-out egregious moves here. None of them worked out - that could still change with one - but they didn't flat-out derail the team.
The Milwaukee Bucks needed to nail their 2023 first-round draft pick. On paper, they got what they needed an an athletic defensive wing, but Beauchamp hasn't worked out so far. Throughout his first three years, the wing has not earned a steady role and faces a make-or-break season in 2024-25 as he aims to prove he belongs not just on this team but in the NBA.
Internally, keeping Serge Ibaka and Jordan Nwora on cheap deals was understandable. The Bucks needed depth at the center spot, and they kept the player they traded for months earlier. Nwora was supposed to play a big role for Bucks that season. However, neither player stood out, and both were moved at the trade deadline to make room for Jae Crowder.
Outside of Portis, Milwaukee's big free agent splash was adding Joe Ingles who, despite coming off an ACL injury, earned a one-year deal worth $6.5 million. Ingles' sweet passing and shooting helped in spurts, but his lack of mobility and athleticism at his age post-injury ultimately prevented him from making as great of an impact as Milwaukee had hoped before he left in free agency.
No. 2 - 2024 offseason
Many would argue that this deserves to take the top spot. It certainly has a case, but it comes in No. 2 for this particular writer. While not coming in at first, there's a ton to love about the Milwaukee Bucks' moves from this past summer.
The good: Signing Gary Trent Jr., signing Delon Wright, signing Taurean Prince, drafting AJ Johnson, drafting Tyler Smith
In the eyes of many, Gary Trent Jr. was the biggest steal of the offseason. A clear-cut starting two, the Bucks inked Trent to a one-year deal worth the minimum. It's a massive win for the Milwaukee Bucks, and Trent should be a key cog. His 3-point shooting and defensive disruptiveness will have him on the floor in crucial moments as he aims to get paid next offseason.
Sticking with minimum deals, the Bucks beefed up their bench with Delon Wright and Taurean Prince. Neither player is the flashiest name, but they both patch roster roles on the defensive end and give the team more versatility. Given the financial limitations Milwaukee is battling, getting these two for cheap is a sizeable victory. Expect both to play strong roles and bring more needed defense.
The Bucks needed more youth this offseason. When the picks were made, many were not fond of the moves for AJ Johnson and Tyler Smith, two 19 year olds. The potential is undoubtedly there, but fans were concerned when exactly these two youngsters may be ready to help. It almost certainly will not be this coming season, but the year after? The year after that? It is unknown.
Thankfully, both raised their stock in the Summer League, primarily Johnson, the first-round pick. His speed, burst, athleticism and fearlessness created several eye-catching plays, which got Bucks fans leaning forward in their seats. It might take time, but if these two pan out, Milwaukee may have extended its title window this past offseason. It was a big gamble by Jon Horst.
The bad: N/A (yet)
On paper, all of Milwaukee's moves appear to be good. Of course, that could change in time, but for now, there is reason for optimism. Perhaps we'll circle back next offseason.
No. 1 - 2023 offseason
Hear this writer out.
For most of the 2023 offseason, it felt like the Milwaukee Bucks were taking a similar approach to the 2022 offseason, except with a new coach at the helm. Their primary focus was bringing back familiar faces while tweaking around the edges. Of course, things ended up getting far crazier than that over the summer. The star power and youth they added/retained lands this offseason at No. 1.
The good: Trading for Damian Lillard, re-signing Khris Middleton, re-signing Brook Lopez, extending Giannis Antetokounmpo, signing Malik Beasley, drafting Andre Jackson Jr., drafting Chris Livingston, re-signing AJ Green
Many would put the Damian Lillard trade in the mixed slot. Sure, things didn't go according to plan in his first season, but the Bucks didn't add him for one season. Lillard should be much better this year, and if he looks like the Damian Lillard of old, the Bucks will be justified in trading away two starters in Jrue Holiday and Grayson Allen and draft capital.
The Damian Lillard trade led to Giannis Antetokounmpo adding three more years to his own contract, and it's always nice to know the franchise cornerstone is sticking around. Losing Khris Middleton or Brook Lopez for nothing would have been devastating, so while the Bucks gave them a lot of money, they really didn't have much of a choice from a team-building perspective.
Malik Beasley was given a completely different role after the Lillard trade went down, but on a deal worth the veteran's minimum, he was still a strong pickup. Starting for most of the year, he had the best 3-point percentage of his career, which was good value.
The Bucks also did a lot for their youth this offseason. Re-signing Green for cheap was a good move, and the hope is he can leap into the rotation. Draft picks Andre Jackson Jr. and Chris Livingston both check off boxes for the Bucks in terms of athleticism and defense, and the hope is that they can be in the rotation in time because of those attributes.
These moves allowed Milwaukee to keep contending in the moment while also adding youth to try and extend the title window.
The bad/mixed: Hiring Adrian Griffin, signing Robin Lopez, re-signing Jae Crowder, signing Cam Payne
While there were plenty of good things to come out of this offseason, the bad still loomed large for the Milwaukee Bucks in one massive regard.
Hiring Adrian Griffin was a puzzling move from the start. While he may have been a decent coach in time, the Milwaukee Bucks didn't have time to wait. A rookie head coach didn't make much sense for a team needing to win now, and management clearly realized that far too late, opting to fire him before his first season even ended. It's certainly a blemish for the Bucks.
In free agency, the signings of Robin Lopez, Jae Crowder and Cam Payne never moved the needle. Lopez and Payne didn't make it past the trade deadline, and Crowder got hurt early in the season, never finding his place in the rotation upon returning. All on minimum deals, it didn't hurt too much.
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