The Cleveland Cavaliers have found a couple of young stars in the NBA Draft in recent years. Darius Garland is already an All-Star, Evan Mobley will soon be on, and Collin Sexton is both polarizing and still a success of an eighth-overall pick. While Jarrett Allen and Lauri Markkanen came via trade, the Cavs would not be where they are without nailing some draft picks.
On the other hand, they have also had some big draft whiffs. We wrote yesterday about how the Cavs would be in a very different place if they had drafted Tyrese Haliburton instead of Isaac Okoro in the 2020 draft, and the Houston Rockets are currently developing Kevin Porter Jr. after the Cavs organization gave up on him for primarily character reasons.
The Cleveland Cavaliers look like they might move on from Dylan Windler. If they do, these three trades could mean a second chance for Windler’s career.
The biggest draft mistake thus far, however, has been Dylan Windler. Over the past five years the Cavs have drafted seven players in the first round, and he is the only one who is not a rotation player. He has been ravaged by injuries, but even mostly healthy last season he couldn’t establish himself or crack the rotation. It seems very likely that his time in Cleveland is done.
If the Cavs and Sexton agree to a deal in the coming weeks, the organization will need to cut a player to get down to the maximum of 15 on the roster. A prime candidate would be Windler, but with four million guaranteed for next season the Cavs could look instead to trade him and open that space back up under the luxury tax.
Let’s look at three options for the Cavs as they explore a trade, and how each landing spot could be an opportunity for Dylan Windler to get a second chance. How can the Cavs open up a roster spot and put Windler in a new environment to take another crack at an NBA career?
3 Dylan Windler trades for Cavs: Indiana Pacers
The simplest way for the Cleveland Cavaliers to find a home for Windler would be on one of the remaining teams with cap space to simply take him in. The Indiana Pacers are still sitting on a large amount of space, and are also a rebuilding team without a lot of depth at the 3; similar to Cleveland, their perimeter talented is congregated at the 1 and the 2.
Indiana here would take a flier on Windler for nothing; the Cavs wouldn’t have to pay to dump the salary, and the Pacers wouldn’t pay to add a young wing with upside. The 2023 second-round pick sent back is one the Pacers own from the San Antonio Spurs, and being protected 31-55 means it has close to a zero percent chance of conveying.
The Pacers still have around $30 million in cap space, so they would still have plenty in the tank to take on bad money during the year. Aaron Nesmith might get the first crack at starting at the 3, or they could slide over Chris Duarte or Bennedict Mathurin, but there is almost certainly room for some rotation minutes for Windler while the Pacers evaluate him.
3 Dylan Windler trades for Cavs: Orlando Magic
In this trade scenario, the Cavaliers find another rebuilding team with a lack of small forwards to move Dylan Winder to. The Magic have bolstered their backcourt and their bigs lately, but could use some depth on the wing behind Franz Wagner. Dylan Windler could have a chance to catch on and join the core they are bringing.
In this deal the Cavs move two players for one, opening up that roster spot they need to re-sign Collin Sexton and getting a solid veteran wing in Gary Harris in return. Osman has value on a fair contract, and the Magic could keep him or more likely flip him to another team looking for wing depth.
The Cavs take on a slight bit of salary here, which may be a non-starter for them, but they would do so to add a solid contributor who has playoff experience. Harris could start at the 2 or be the bench wing complement to Collin Sexton, and he is no stranger to a small role as an off-ball player after his years running with Nikola Jokic. His non-guaranteed deal for 2023-24 is also useful to a team that may use cap space next summer, or may want to use it the one after that.
The Magic might be hoping to get more back for Harris, but if they don’t get a better offer then this gives them a young player to take a chance on, a veteran wing to flip, and a reasonable second-round pick. It’s in the realm of possibility that this is enough to get such a deal done.
3 Dylan Windler trades for Cavs: Toronto Raptors
There is one other possible route for a Windler trade that doesn’t involve a rebuilding team, and that is a successful team with a strong history of player development like the Toronto Raptors. They don’t have a spot in the rotation earmarked for him, but they do have a trade exception from the Goran Dragic trade that would allow them to take in Windler without sending anything in return.
In Windler, the Raptors get a shot at another big wing / forward like they are stocking the roster with. They have a strong developmental system that runs through their Raptors 905 G League affiliate, and Windler would get exposure to a successful team like the Raptors and get playing time across town. If he can stay healthy, he could work his way into a role coming off the bench for Toronto.
The Cavs aren’t getting anything back in this scenario except the roster spot and the room under the tax, but if Sexton does return they could be in a bind. This would be a chance to move Windler without attaching an asset. If the market is tougher, then the Cavs may be shopping with a second-round pick attached to Windler, and in that scenario, Indiana and San Antonio probably step right up.
Dylan Windler is a talented player and could still become an NBA rotation player. Perhaps he is a really late bloomer and becomes even more. The NBA will always take a second chance on big wings who can shoot, so Windler should have a market. These are three of the teams where he could get a second chance.