The Milwaukee Bucks took a low-risk, high-reward chance when they brought former lottery pick Justise Winslow into their G-League system via the Wisconsin Herd. But nearly two months into the season, the gamble remains in limbo.
Many fans might not even know that Winslow is under the organization's payroll, and that would be perfectly understandable. The 6-foot-6 Winslow, once heralded for his versatility and defensive potential, has made just a single appearance for the Herd, raising questions about whether this experiment will even bear fruit for the Milwaukee Bucks.
Winslow’s debut came on November 8 in a loss to the Iowa Wolves. In 19 minutes, he showed glimpses of his multifaceted game, scoring 19 points on 7-of-14 shooting, grabbing seven rebounds and blocking two shots. His defense and hustle were present, and he finished as the only starter with a positive plus-minus in the losing effort. However, his struggles from beyond the arc (1-of-4 on threes) and a lone assist underscore the inconsistency that has marked his career.
The 28-year-old hasn’t played since that game due to a hamstring injury, leaving his status with the Herd—and, by extension, his potential path back to the NBA—uncertain.
The idea of Justise Winslow is more exciting than reality
Winslow entered the league with high expectations as the 10th overall pick in the 2015 NBA Draft, spending his first five seasons with the Miami Heat. Injuries and inconsistency have plagued his career, leading to stints with the Grizzlies, Clippers, Trail Blazers and a brief 10-day contract with the Raptors last season.
His recent history in the G-League with the Raptors 905 highlighted both his potential and limitations. Winslow averaged 15.1 points, 7.5 rebounds and 2.6 assists in 27 minutes per game, but his pedestrian shooting splits—47.6 percent from the field, 29.5 percent from three and 66.7 percent from the line—painted a picture of a player still struggling to find offensive consistency.
At this point, it's probably a fair assumption that Winslow is just who he is as a scorer. That should be fine, but his continuing injury history is also a problem that teams have to watch out for.
Milwaukee likely saw Winslow as a potential two-way contributor who could provide depth and defensive versatility if he proved healthy and productive. His size, defensive instincts and ability to handle the ball in transition fit the mold of a modern NBA role player fit for this era. For a Bucks team with championship aspirations, having a player like Winslow in the pipeline could be valuable, especially as the season grinds on and injuries or fatigue take their toll.
To be candid about it, there's little chance at this point that Winslow is able to play well enough to make it onto a Bucks roster that already has an offensively-impaired defensive stopper in Andre Jackson Jr. In a league that pursues versatility above all else, you can never have too many wings, but there are probably better options than Winslow out there at this point, considering the numbers he's still putting up.
Still, the Bucks are very clearly in dire need of size and versatility, as evidenced by their losses against fellow contenders like the Boston Celtics and the Cleveland Cavaliers. Having Jackson as your best wing defender may not cut it going forward, and it's perfectly understandable that they're looking everywhere they can for new (and not-so-new) talent.
The Bucks are still waiting on their gamble to pay dividends
The clock is ticking. At 28, Justise Winslow’s window to establish himself as an NBA-caliber player is narrowing.
For the Bucks, this move (and in case you missed it, their other G-League signing in Dennis Smith Jr., too) is just one of those low-risk opportunities that contenders must explore to sustain success. If Winslow can eventually contribute, it’s a win. If not, the Milwaukee Bucks lose little beyond the roster spot and development time invested.
As the Bucks navigate the long NBA season, they’re undoubtedly keeping tabs on Winslow’s progress—or at the moment, lack thereof—with the Herd. At the end of the day, it's still a gamble that might pay off. His potential to provide defensive versatility and experience could still be valuable for Milwaukee, but until he’s back on the court, it remains just that: potential.
For now, the Milwaukee Bucks’ gamble on Winslow is a story of patience, hope, and the lingering question of whether a former lottery pick can find his way back to relevance.