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Former NBA executive details how Cavs could land Ben Simmons or Jerami Grant
- Updated: December 30, 2021

Former NBA executive John Hollinger recently painted a couple of interesting trade scenarios for the Cleveland Cavaliers.
He speculated about how the team could acquire Detroit Pistons star Jerami Grant or Philadelphia 76ers star Ben Simmons.
“Could they be a player for a wing on the trade market?” Hollinger wrote of the Cavs. “(Presuming such a thing existed?) Could they get involved in something (rubs palms) big? I mentioned [Dennis] Schröder above, but he could also be a small piece of something bigger in a three-team construction where the main event is [Collin] Sexton and [Ricky] Rubio for a $20 million-ish player; consider a deal for Jerami Grant, for instance, where the Cavs send out Sexton, Rubio, Dylan Windler and their 2022 first to Detroit and end up with enough room below the tax to stuff Schröder into the trade.
“If you want something even more grand, what about Sexton, Rubio, Windler and two firsts to Philadelphia for Simmons? Is it crazy to bring in Simmons when Darius Garland is thriving on the ball, or is it wild to think about a Simmons-[Evan] Mobley-[Jarrett] Allen frontcourt terrorizing the league on defense? It also puts the Cavs slightly into the tax, but damn the financial torpedoes, we want some trades!”
The Cavs have undoubtedly been one of the best stories of the 2021-22 NBA season so far, but the injury bug hasn’t been kind to them.
With Sexton and Rubio on the shelf for the remainder of the season, the team would be wise to explore as many avenues as possible on the trade market. Of course, no team should make a deal just for the sake of making a deal, but if the right opportunity comes along, Cleveland should take it.
The Cavs are 20-14 on the season. They’ll face the Washington Wizards on the road on Thursday.
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