With Eric Bledsoe going off the market, the Cavs still need someone to pick up the slack at point guard. Somehow Jose Calderon and Derrick Rose aren't working out. Who's left? Outback Jesus.
Trade season is early this year in the NBA. The Eric Bledsoe saga included mention of Cleveland as a destination, as the Cavs had been mentioned over summer as a landing spot for Bledsoe. Obviously, it didn't come to fruition. For Bledsoe, he'll enter a more functional situation in Milwaukee where he has solid players around him and a legitimate chance to make a playoff run.
More importantly, it means that the Cavs have to look elsewhere to solve their point guard woes.
While rumors swirl that Phoenix will look to quickly trade Greg Monroe, and the Cavs do have front-court depth issues, Monroe is probably not the answer. He has been pretty solid defensively thus far, allowing a lower restricted-area shooting percentage than several big-name defenders (Gobert, Marc Gasol, and Adams among others), but he has also been a substantial minus in the box scores this year. So Greg Monroe is going to have to show up in someone else's article - he's not coming to the Cavs. The Cavs have bigger fish to fry.
How do the Cavaliers solve their point guard issue?
First, it seems relevant to dive into just how much of an issue the point guard spot is. Jose Calderon was signed first, then Derrick Rose came later, then the trade for Isaiah Thomas happened. Thomas may be back soon, he may never be back to his old self, or he may be back late but healthy. Who knows?
What we do know is that Jose Calderon is unplayable and Derrick Rose is the antichrist of point guards. Through the first seven games he has played, Rose has 12 assists and 19 turnovers. He is also shooting 23% on three-pointers. If you average his stats out to their per-100 possessions rates, he's setting career lows in points, rebounds, assists, and steals while averaging career highs in turnovers, fouls, and defensive rating.
He's bad. It's slightly masked by the fact that he can still get to the rim (although he's taking the second fewest foul shots per 100 of his past eight seasons). Again, it's bad.
Know who's not bad at point guard when he's playing in Cleveland? Know who plays some decent on-ball defense? Know who gets his teammates involved and only shoots when wide open? Know who is beloved beyond reason in Cleveland? Know who has been playing worse since he left Cleveland and will now be seeing even fewer minutes, so he has a good reason to get shopped?
Outback Jesus himself: Matthew Dellavedova. Let's take 4:00 and watch one of the strangest, most wonderful highlight videos of all time.
Would Delly actually solve anything?
Admittedly, I don't know. I don't know why Delly isn't as good as he was with the Cavs: It seemed like his stroke started to disappear around the Finals run of 2016 and it never really came back. OBJ shot 40% or better on three-pointers for two full seasons before dropping to 37% in his first year with Milwaukee and dipping even lower this year.
But, and hear me out on this one, he would do the things that no one on the Cavs is doing right now. What does that mean? Well, if you Google "Delly streamable" to find streamable clips of this guy, three of the first five results are of Delly setting screens. In fact, it's not until the 7th result that we get this play.
He throws lobs, he pesters opposing players, he gets under guys' skin, he moves without the ball, and most importantly, he never ever relaxes. The Cavs have looked lazy and slow. If Delly is in the wrong spot, he's committing 100% to being in the wrong spot and is going to make mistakes at full-speed. He's not going to just shrug his shoulders and point fingers the way literally everyone on the current Cavs does. He simply doesn't seem wired that way.
The only thing holding the Cavaliers back from going after Delly is the trade-pieces. If the Cavs believe that Dwyane Wade is the guy from the past three games and not the guy from the first six, then Iman Shumpert is expendable. They've been shopping him for a long time but haven't found any takers. Similarly, Dellavedova is expendable to the Bucks: he'll be behind Brogdon, Middleton, and Bledsoe, and probably sharing situational minutes with Tony Snell (who has seemingly been shooting 90% from deep over the past two seasons).
The only downside here is that Shump would be pretty redundant in Milwaukee. A third team might be necessary and maybe a deal could be cut where Shump goes to Sacramento, Kosta Koufos goes to Milwaukee, and Delly comes to Cleveland. Who says no? Looking a little deeper, Milwaukee would effectively be trading Dellavedova and Monroe for Koufos and Eric Bledsoe. That's probably an upgrade. If it's piece by piece, Bledsoe is a huge upgrade over Delly and Koufos is probably a slight downgrade but $10m less expensive. The Cavs would be swapping Shump for a legitimate NBA point guard who does all the things that their current point guards don't do (namely play like a point guard). Sacramento is the question mark, as they're basically acting as enablers. Shumpert would be a defensive upgrade over several of their young guys, and if his shot is around league-average, they could run out a hell of an exciting small-ball lineup of Fox, Bogdanovic, Shump, Hield, and Stein. That would be fun to watch for three-minute bursts, and that's good news for the Kings right now.
That's the one. In the words of Jean Valjean, bring him home.