Even after signing Gary Trent Jr. to fill out their standard roster, the Milwaukee Bucks are still doing homework on available free agents.
Per The Athletic's Shams Charania, the Bucks conducted a workout in Las Vegas that featured many former NBA players who still believe they have something to give. With no roster spots up for grabs at the time of this writing, any thoughts of bringing another player in are dormant. However, if someone performed well enough, the team may keep tabs on them for training camp or when they free a spot.
If a roster spot does open up and the Bucks feel like giving one of these attendees a chance, which of the bunch would fit the best? Let's rank the rumored players who were there based on how well they'd fit with the current iteration of the Milwaukee Bucks.
No. 5 - Isaiah Thomas
It's been a long, grueling road for Isaiah Thomas over the past couple of years. The two-time All-Star has bounced around the league searching for a home to prove that he still has something to provide despite the countless injuries he's battled over the years. Above all else, one has to admire Thomas' persistence to stick around in the NBA. Many others might have given up at this point.
Although he's the most recognizable name on this list, Thomas just doesn't exactly fit what the Bucks need more of at this point. Another ball-handler wouldn't be the worst thing to beef up the bench, and bringing in another battle-tested guard like Thomas to help mentor newcomer AJ Johnson would be a reasonable decision as well.
Yet, a 5-foot-9 35-year-old who has never been known for defense would not make a ton of sense on this roster as currently constructed. As evidenced by their moves this off-season, an objective this team clearly had this off-season was to get younger, more athletic and improve defensively, and they wouldn't get any of that from Thomas.
No. 4 - Will Barton
In today's NBA, a team can never have too many wings. Over these past few years, injuries have taken a toll on Milwaukee's rotation, particularly with Khris Middleton in the 2022 NBA Playoffs, meaning it'd be a reasonable move to stock up on as many playable wings as possible. That's why this workout was littered with former NBA wings, including Will Barton.
During his 11-year stay in the NBA before he went to play overseas last season, Barton was a quality second-unit spark who could provide instant offense. He averaged 11.2 points while knocking down 35.5 percent of his triples in that span. Another capable scoring threat off of the bench wouldn't hurt the Milwaukee Bucks, as that has been a problem for them over these past few years.
It must be noted that the Bucks were linked to Barton in the rumor mill early in 2023 when he was being floated as a buyout target, so he is someone they have familiarity with. Speaking of familiarity, Barton knows Milwaukee point guard Damian Lillard quite well, as they played together in Portland in the early stages of their careers, which cannot be overlooked here.
Despite all of that, Barton lands at fourth on the list because the three players above him possess more potential and fit the needs of this roster better. At 33, he's not the oldest player on the block, but he's also not as young as he once was. During his final season in the NBA in 2022-23, Barton showed noticeable signs of decline. It might be wiser to take a flyer on someone above him.
No. 3 - Justise Winslow
Just like Thomas, Justise Winslow is another player who's endured plenty of adversity due to injuries. The former top-10 pick played just 114 games during his final four years in the league, with a handful of teams taking a flyer on him to try and unearth some of the potential he undoubtedly possessed. Perhaps the Milwaukee Bucks could be next on that list.
When healthy, Winslow has what it takes to be an incredibly versatile defender. Standing at 6-foot-6, 222 pounds with a 6-foot-10 wingspan, he's got a Swiss Army Knife build that allows him to switch onto opponents of different sizes and hold his own. Even if it's just for depth, another stout defender could do this Milwaukee Bucks roster plenty of good.
To show that he still had fuel left in the tank, Winslow played in the G-League this past season and impressed. He averaged 16.7 points, 8.6 rebounds, 2.8 assists, 1.8 steals and 1.1 blocks per game, serving as a do-it-all player. Those numbers won't translate, but if Winslow can make an impact as a glue guy while staying healthy, there's a place for him in the NBA.
Like Barton, Winslow is another player who has suited up alongside Damian Lillard back in Portland, adding to that familiarity aspect.
The big concern with Winslow, and why he lands at third on this list, is the injury history. Although he impressed in the G-League, there are questions as to whether he can simply stay healthy if given an opportunity. At 28, he's still fairly young, so he'd fit right in with Milwaukee's recent youth movement, but he would definitely not be without risks.
No. 2 - Jaylen Nowell
Investing in youth has been a priority for Milwaukee this off-season. In addition to drafting two young players in AJ Johnson and Tyler Smith, they also added Stanley Umude via a two-way deal. If they want to keep the ball rolling in that regard, it makes sense that Jaylen Nowell was in attendance at this workout hosted by the Milwaukee Bucks, as he just turned 25 years old.
During his first four seasons in Minnesota, Nowell, a second-round pick of the Timberwolves in 2019, showed signs of potential. His biggest boon was his offensive output, having put up 9.1 points per game in that span. Yet, he wasn't able to truly put the pieces together in his game and was let go. He played just 13 games for Memphis and Detroit this past season.
Nowell showed improvement in his game during his G-League stint, putting up 17.4 points, 3.6 assists and 3.5 rebounds while shooting 38.5 percent from long range in 28 games this past year. Of course, the G-League is a different game than the NBA, but those numbers are potential-filled. At 25, he's still young and has plenty of time to grow and develop.
If the Bucks want wing depth and one more young piece they could possibly mold into a contributor down the road, bringing Nowell in would make sense. He wouldn't do much to help their defense, as that has never been the strongest part of his game, but he could give them another young guard with scoring chops who could learn behind Gary Trent Jr. and Khris Middleton.
No. 1 - Hamidou Diallo
Based on Milwaukee's needs and fit, the most interesting free agent rumored to attend this workout is Hamidou Diallo. The high-flying wing is about to turn 26 years old and could make some sense for the Milwaukee Bucks if stocking up on wings is still a prominent goal of theirs.
It's no secret that this roster has lacked athleticism for quite some time, and Diallo could help provide it in a big way. The guard has always been known for his leaping ability, which he has used to throw down his share of highlight dunks or swat shots. With athleticism like that, he's a spark who can make a play at any given moment.
At 6-foot-5 with a 6-foot-11 wingspan, Diallo also has solid size and length, which has helped him be a fine enough defender at the NBA level. Another capable wing defender would be a justifiable addition to this Milwaukee roster. The biggest downside with Diallo is that he's never been much of a threat on the offensive end, at least in the NBA, which could limit his impact.
In the G-League, Diallo put together a season that should catch some eyes. He averaged 20.1 points, 7.7 rebounds, 1.7 assists and 1.3 steals per contest. Those are undeniably captivating numbers from the 25-year-old that showcase he can be a jack of all trades on the court. If the Bucks found a way to bring him aboard, it would be a low-risk move to boost their athleticism on the wing.
Although Diallo lacks the shooting and experience that several of these other candidates possess, his electric athleticism, age and versatile defense put him atop of this particular ranking.
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