There’s a quiet irony in watching the Milwaukee Bucks championship window flicker as so many of the team’s most valuable pieces thrive elsewhere. As the Bucks face an uncertain offseason, their recent past reads more like a cautionary tale of talent lost that eventually caught up to them.
Milwaukee built a contender the old-fashioned way: with patience, player development, and gritty, defense-first basketball. They cashed that in for a title in 2021, but never stopped to think about sustainability. In the years since the front office has continued mortgaging depth and flexibility in favor of chasing vets to keep their marriage with Giannis Antetokounmpo alive.
Instead, fans have watched familiar faces blossom elsewhere, while the Bucks leaned heavily on veterans with diminishing returns. The latest blow came when Damian Lillard’s Achilles injury effectively iced the Bucks’ postseason ambitions and raised existential questions about the franchise’s future.
Now, as speculation around a possible Antetokounmpo trade swirls, it’s worth looking back at the players the Bucks once had and still desperately need.
Jrue Holiday
More than a stat sheet warrior, Holiday was Milwaukee’s metronome. His perimeter defense, poise, and basketball IQ served as the Bucks’ point-of-attack anchor during their title run. He is nearing his twilight but proved his value in year one with Boston as one of the best two-way defenders in the entire NBA en route to adding another championship to his trophy collection. Numbers have never accurately explained his value though.
His number is never popped off of the page or the box score. As a true freshman, he helped lead UCLA to the Final Four averaging a meager 8.5 points per game, and parlayed that into becoming the 17th overall pick. Holiday was a culture-setter, the type of guard who does the little things that win playoff series. Since his exit, Milwaukee has struggled to replace his defensive leadership. His departure in the Lillard trade netted flash, but cost the Bucks their foundation.
His salary would have also given the Bucks more flexibility than Lillard’s max contract. Holiday has only been named to a pair of All-Star Games, but every team he’s been traded to has immediately peaked when he arrived and collapsed after his departure.
Donte DiVincenzo
DiVincenzo has worn a number of different jerseys since being traded to the Sacramento Kings for Serge Ibaka. Jon Horst has made a number of short-term deals that have hampered the Bucks in the long term, but DiVincenzo was one of his worst because they got nothing in return for him. DiVincenzo was a young athletic 2-guard who should have guarded them more in a trade than the decrepit final years of Ibaka. He’s struggled to define his role alongside Anthony Edwards in Minnesota, but in New York last season, DiVincenzo was a scorer who filled gaps for the Knicks and could get hot in a hurry.
Malik Beasley
Malik Beasley’s sharpshooting was instrumental to Detroit’s ascension this season. He ranked third in three-pointers made on a measly one-year, $6 million deal. Beasley is one-dimensional, but it can never hurt to have a stockpile of shooters at your disposal. The Bucks struggled to space the floor when Damian Lillard and Gary Trent weren’t on the floor. Kyle Kuzma failed to knock down shots. Beasley on the wing or short corner would have opened the floor even more for Lillard or Antetokounmpo to operate.
Grayson Allen
Allen was a thoroughly detestable player for reasons beyond his resemblance to Ted Cruz, but at least his nastiness translated to defensive intensity. Cruz embodied Coach K’s ‘slap the floor’ intensity. He's a 40-percent shooter from beyond the arc and would have been one of the few weapons with serrated edges on both ends of the floor. Alas, he was dumped as a trade piece in the Lillard acquisition. Since then, the Bucks have lacked grinders who can detonate an offense with guile and grit. Andre Jackson Jr. was a formidable defender for much of this season but was too poor of a shooter to rely on for heavy minutes.
Sam Merrill
Merrill has established himself as one of the league’s most accurate spot-up sharpshooters in Cleveland. In Game 2 against Cleveland, Merrill rang up a career-playoff-high 14 points, when three starters sat to rehab injuries. Merrill was a homegrown player the Bucks found at the end of the first round.
Ironically, Merrill was lost in a trade for Allen and was ultimately waived. He’s not as versatile as Holiday or Allen, but the Bucks need young players who form synergy with the vets on their roster. By moving so many pawns out for grizzled vets, Milwaukee has become a destination for players on the back end of their careers.
AJ Johnson
If the Bucks are intent on beginning a rebuild, trading Johnson in the Kuzma deal may look even more short-sighted and foolish than it did at the time. The Bucks are devoid of developmental stars and to unload Johnson for Kyle Kuzma was malpractice.
There were better ways to get under the second apron. In Milwaukee, Johnson was superglued to the bench. After removing the splinters upon his arrival in Washington, he was given more playing time and flourished in spurts. Johnson will be only 21 next season and is the type of player Milwaukee should be grooming on their roster if they’re moving on from Antetokounmpo this summer.
Malcolm Brogdon
Mr. President cut his teeth in the NBA with the Milwaukee Bucks, but was traded once his rookie extension. Now 32, Brogdon has been plagued by injuries throughout his career, but when active was one of the NBA’s most efficient guards. Brogdon played only 24 games due to a variety of injuries but as an expiring contract, he’d have been a much more valuable asset off of the bench in Milwaukee when healthy.