In 2019, the Cleveland Cavaliers selected a young wing prospect who had promise to become a prototypical modern 3-and-D NBA wing.
Through four collegiate seasons with the Belmont Bruins, Dylan Windler steadily improved his production and role with the Bruins. In his fourth and final season, Windler averaged 21.3 points and 10.8 rebounds per game while shooting 42.9 percent from three-point range on high volume. Despite entering the NBA draft as an older prospect, Windler projected to be a high-end wing role player.
Standing at 6-foot-8 and displaying ideal two-way talent, the Cavaliers targeted Windler with the 26th overall pick. The 23-year-old rookie looked like a high-ceiling, low-to-mid-floor role player who could perfectly fit into a rebuilding Cavaliers roster. He would have ample opportunity and time to develop into an NBA role.
Unfortunately for both Windler and the Cavs, Windler was consistently injured and unavailable to step onto the hardwood. He missed his rookie season and only appeared in 31 games in year two. His inconsistent availability kept Windler from finding his fit in Cleveland's system, shooting just 33.8 percent from deep in this second season. Year three gave Windler 50 appearances, but he averaged only 9.2 minutes in those games.
Eventually, Windler lost his foothold with the Cavaliers organization, rarely playing with the main roster and instead being left behind with the G League affiliate Cleveland Charge. In the 2023-24 season, his G League production gave him another chance at the league, joining the New York Knicks' G League Winchester Knicks squad before bouncing later that same season to the South Bay Lakers and eventually the Atlanta Hawks.
Windler is finally finding success halfway across the globe
Windler left the NBA in 2024, heading to the National Basketball League (NBL) in Australia to join the Perth Wildcats. In his first two seasons with Perth, Windler has finally stayed healthy and become a valuable professional player. The potential the Cavaliers saw in 2019 may have not materialized in the NBA, but Windler is becoming exactly what he promised.
In Perth, Windler is averaging 13.6 points over the first seven games of the regular season. He has shot nine-of-30 from three-point range over those games, showing potential to reclaim his title as a long-range sharpshooter that he earned in college. In his first full season with the Wildcats, Windler shot 39.2 percent from three and averaged just over 11 points per game.
At 29-years-old, Windler has suddenly emerged as a 3-and-D talent who could soon earn the attention of NBA scouts once more. His tall frame and two-way talent is the exact skillset every NBA team seeks out, and as the international game grows, the league has seen more players earn a second chance in the Association. Players like Guerschon Yabusele and Dante Exum may have paved the way for Windler's eventual NBA reunion.
The basketball world, particularly the NBA, is full of "what if" stories of players who should have become something great. In recent years, the Cleveland Cavaliers are no stranger to this phenomenon, but Dylan Windler may be the hardest to accept. As he rebuilds his basketball promise, the Cavs may need to take another look at the former Bruins great.