After entering the offseason with question marks about their future, the Cleveland Cavaliers were able to pull off the unthinkable this offseason and retain all four of their top players by handing Donovan Mitchell, Evan Mobley, and Jarrett Allen new extensions to remain with the team, and Darius Garland, into the future.

If that was all the Cavaliers did this offseason, the summer would be considered a win, as Cleveland had some horrible injury luck last season and will undoubtedly be better this fall if everyone can stay healthy, but they have added interesting talent to go with new head coach Kenny Atkinson in first-round pick Jaylon Tyson, with the potential to round out the rotation with a few more two-way contract players.

And yet, the most interesting maneuver of the summer is the one the Cavaliers didn't make, as they were widely expected to move on from former fifth-overall pick Isaac Okoro in a sign-and-trade deal but have yet to find a deal with the restricted free agent, arguably the biggest name left on the market despite free agency having “ended” for most teams about a month ago.

What gives? Why didn't Okoro, one of the better wing defenders in the NBA who is somehow only 23, not draw enough interest to bring Cleveland back a quality player of at least a draft pick, allowing the team to go about their business without being held effectively hostage by his contract status? Did the team simply wait too long, and all of the money dried up? Or were the offers never quite good enough to make it work it for Cleveland?

Well, according to Jake Fischer of Yahoo Sports, the Cavs did receive some interest in Okoro and even had talks that would have brought back a very interesting player in a hypothetical sign-and-trade, but the conversations never got to the proverbial endzone, even if most fans probably would have been very happy with the deal all things considered.

Could it be his non-developments on the offensive end of the court, with the 6-foot-5, 225-pound player largely still considered a one-way player who doesn't take enough 3s to truly space the floor in the playoffs?

Cleveland Cavaliers forward Isaac Okoro (35) talks with referee Mark Lindsay (29) in the second quarter against the Orlando Magic during game one of the first round for the 2024 NBA playoffs at Rocket Mortgage FieldHouse.
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The Cleveland Cavaliers let a deal with the Brooklyn Nets fall through

In the NBA, it takes two to tango, so the Cavaliers really couldn't get a sign-and-trade done if they didn't have another team interested in acquiring the former fifth-overall pick out of Auburn, right?

Technically, that is true, but according to Fischer, the Cavaliers did have an interested party who was willing to talk about a very interesting player in a sign-and-trade deal for Okoro in the Brooklyn Nets.

Though a deal ultimately didn't come through, and has become harder to pull off with each passing month as money around the NBA dries up, the prospects of sending Okoro to the Nets in a sing-and-trade in a deal featuring Dorian Finney-Smith would have changed the evalaution of the offseason considerably.

“I know there was some reporting about there being a Nets package idea where [Okoro] would go to Brooklyn, and there'll be something with Dorian Finney-Smith going back,” Fischer explained via Sports Illustrated. “I don't think those talks got really, really substantial to my understanding. I just don't think it can even happen right now after the salary stuff has all shifted out. I don't think Brooklyn has the room to make that happen. And bringing back Dorian's like $14 million would be challenging for that first apron stuff that we're talking about with Cleveland in general… I think Okoro could very easily take that one-year qualifying offer.”

Heading into the offseason, the Cavaliers' biggest need, other than bringing back their own players, was finding a complementary fifth starter to help fill in the gaps between Mitchell and Garland at the guard spots and Mobley and Allen in the frontcourt. Cleveland tried Okoro, they tried Max Strus, they've tried Carvis LeVert, Dean Wade, and even Georges Niang but through it all, the Cavaliers have never found “the guy” for the team heading into the future.

While it's impossible to know if DFS would have been that guy without actually slotting him in at the three spots, especially considering everyone is now playing under new head coach Atkinson, Finney-Smith has been a high-level player on multiple quality teams over the years and is practically the prototype for a modern-day 3-and-D wing. Even if Okoro has more upside, considering his age, it's hard to see how the Cavaliers are better in 2024 with the Auburn product on the roster versus DFS.

Brooklyn Nets guard Dennis Smith Jr. (4) looks to drive past Cleveland Cavaliers forward Isaac Okoro (35) in the fourth quarter at Barclays Center.
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