The Knicks made a surprising two-way move this offseason that involved signing a player from the team New York beat in the first round of the playoffs. Dylan Windler played in only three games for Cleveland last season due to an ankle sprain and missed the postseason entirely.
The Knicks signed Windler to a two-way contract at the end of July and released 2022 second-round draft pick Trevor Keels in the process. The new CBA allows teams to carry three players on two-way deals, and New York had to make room for Windler.
The 26-year-old guard was the No. 26 overall pick in the 2019 NBA Draft and has averaged 3.3 points and 2.3 rebounds per game since making his debut in 2020. The Cavaliers chose not to extend a qualifying offer to Windler, making him an unrestricted free agent and allowing him to sign with the Knicks thanks to ‘The Harry Giles Rule.’
Windler is by far the most interesting of New York’s two-way players. His first few years in the league were riddled with injuries, and that kept him from coming close to reaching his potential in Cleveland. He’s healthy entering the 2023-24 season and will be a player to watch at training camp and preseason.
Former first-round pick Dylan Windler could find his footing with Knicks
Dylan Windler shot 40.6% from three during his four years at Belmont, and the guard’s role in leading the Bruins to the 2019 NCAA Tournament caused him to be a first-round pick.
He hasn’t enjoyed much success in the NBA, and his career started on an unlucky note when he had to miss the entire 2019-20 season due to “ongoing symptoms related to his left lower leg stress reaction” that caused him to have surgery. Since being drafted, Windler’s played in only 84 games.
It seems starting fresh in New York is what Windler needed. As he saw firsthand in the playoffs, the Knicks struggled from three. He was heralded as a three-point shooter entering the NBA draft but has shot only 32.2% from deep. It’s hard to hold that against him too much, as he’s spent more time off the court than on it.
Windler will spend most of his time in Westchester as a two-way player, where his continued development will be key. He’s on a one-year contract, but depending on how things go, he could work his way into a longer deal with the Knicks.
Training camp and preseason will be especially crucial for players like Windler, who will have an opportunity to impress Tom Thibodeau. The coach’s tight rotation doesn’t leave much room for players like Windler to prove themselves, but the guard’s progression is undoubtedly something Thibodeau will be keeping an eye on.