NBA Season Preview 2020-21: 5 big questions for the Cleveland Cavaliers

What’s the best-case scenario for the Cleveland Cavaliers‘ young trio of guards? How do Kevin Love and Andre Drummond work together? We answer these questions and more in our Cavaliers 2020-21 season preview.

1. Who is the Cavaliers’ best youngster in 2020-21?

It’s Collin Sexton. This is absolutely not the Collin Sexton that you saw floundering as a rookie. Quietly, he’s been one of the most improved rookies from the 2018 NBA Draft class, and he was shockingly competent last year, especially after the Jordan Clarkson trade. Without Clarkson, a supreme chucker who Sexton was forced to share the floor with frequently, Sexton averaged 23.3 points, 3.2 rebounds and 3.2 assists per game on 49/44/87 shooting splits across 35 games.

While that’s not a super large sample, it supports the narrative that’s developed over his short career — that Sexton is one of the hardest-working players in the league, that he improves game over game, and that his ceiling might be higher than originally thought.

Heading into 2020-21, with a nine-month offseason to continue improving his jumper and adding strength, and consistent messaging and scheme for the first time in his career, Sexton could be poised to firmly break out as a quality NBA scorer. The expectation should be that Sexton again leads the team in scoring, takes another step towards becoming a quality passer and outside shooter, and consistently providing end of shot clock creation for a team with limited creator options. And this is something he looks more than capable of doing.

2. Are people sleeping on Dylan Windler or no?

Probably not. Windler did look impressive in Summer League last year, and by all accounts is a star of preseason camp in Cleveland. His skill set would be useful in the Cavs’ rotation, where they need high-level shooters across the floor to help create space for both Andre Drummond and Darius Garland. Cedi Osman‘s spot in the starting lineup should probably be considered open season, and Windler’s the best poised to take over.

However, that’s probably too optimistic a view for what Windler’s first season in the league is going to look like. Windler faces the same issue as rookie Isaac Okoro — the learning curve is steep for someone who hasn’t played a game in a while, and Windler’s been out for over a year. Windler also faces the uphill climb for his already thin frame to be able to hold up across an NBA season. Stress fractures aren’t easy to recover from; and if you go off of recent examples like Bradley Beal, Jrue Holiday, and Brook Lopez, they can take multiple seasons to get over. That becomes harder when you’re doing a full season for the first time. So while the theory of Windler is great, it’s very likely that we get ten games into the season and he looks completely overwhelmed instead.

3. Watching Andre Drummond and Kevin Love together is going to be totally         .

We’ll go with “temporary.” Look, Drummond/Love isn’t ideal. It’s not a good defensive pairing, because neither is mobile enough to play a more aggressive pick-and-roll coverage. It’s not ideal from a hierarchy perspective, as both guys will warrant touches at the expense of Sexton, Garland, and Kevin Porter Jr. thanks to experience and salary. And it’s certainly not ideal for the Cavs’ proposed starting lineup combo with Darius Garland, Collin Sexton, and Cedi Osman, a group that had a -31.2 net rating in 49 minutes together last year. Both players were much better paired with Larry Nance Jr. last year, which is good; but you can’t simply start Nance and bring one of the two off the bench, due to Love’s standing with the team and the dollar signs next to Drummond’s name on the salary sheet.

Luckily, the chances that both end the season on the Cavs’ roster is pretty low. Drummond’s massive expiring contract does make him an intriguing trade chip, especially with how many teams are playing small in the regular season, with the Lakers and their Anthony Davis/Marc Gasol center combination looming late in the playoffs. It’s a steep price to pay for someone who is going to be a situational big in a playoff series, but teams like Denver, Toronto, and Portland who have poor big man depth or rough rebounding numbers could look to pull the trigger on Drummond in an all-in move to bolster their playoff rotations.

Love makes even more sense from that perspective, bringing rebounding and the comfort of playing quality complimentary playoff minutes on his resume. His price tag is steeper, but he’s also probably a more sound long-term move for a playoff team. Either way, addition-by-subtraction is probably in the Cavs’ best interest in this situation, and clearing one of Drummond or Love off the books opens up more opportunities for the young guys and more effective minutes next to Nance for the one that stays.

4. What’s the best-case scenario for Collin Sexton, Darius Garland and Kevin Porter Jr. playing together?

Sexton taking a leap as a playmaker and defender in year three is going to do wonders for the long-term health of this trio. Right now, the Cavs have three young guards who are all primarily scorers, with two who aren’t far enough along as passers to really initiate offense at a high level. Garland is able to do that, but his defensive play doesn’t have a high ceiling. The best-case scenario is that Sexton becomes that optimal gap-bridging force as a number one option that makes his counterparts better. Providing more playmaking will let him defer more of the scoring load when Porter is on the floor, and defensive improvement at the point of attack would make the idea of hiding Garland off-ball and letting Sexton take on opposing point guards more palatable.

It’s not an optimal threesome to share the floor at the same time, and especially with Okoro and Windler entering the fold, these three should be in a timeshare for the two guard spots. Porter at the 3 seems great in theory, but in execution, he’s not quite strong enough to hold up defending the league’s bigger t3s, and there aren’t enough off-ball cutters and shooters on the floor with them together. But Sexton improving as a complement to both would let them make decisions on which players to keep long term because it would create a more ideal environment to evaluate their strengths and weaknesses.

5. What’s Isaac Okoro’s rookie year theme song?

So I’ll tell you all the story

about the joker and the thief in the night

There are two forces at work for Isaac Okoro’s overall ceiling — and how these two forces battle this year goes a long way towards determining his final outcome. There’s the joker, which is Okoro’s jump shot. It’s the biggest reason to doubt Okoro’s long-term success. Okoro wasn’t even a 30 percent shooter from outside in college, and the hitch in his jump shot really ruins what is an incredible defensive prospect on the wing. It’s the formidable force that’s holding him back from being a nearly perfect complementary player to the Cavs’ young guards.

The other force is the thief, played by the Cavs’ shooting coaches. The staff has done a good job of working on improvements with several Cavs players, including Sexton, Osman, and KPJ. Now they face their biggest test — fixing Okoro’s jumper, at least to the point where he’s comfortable taking 3s to keep the defense honest. With that, Okoro can put his passing to use as an asset on offense. With that, he’s not a crutch on that side of the ball. With that, we get to see what Okoro’s defensive capabilities look like when fully unleashed.

So that’s the song of Okoro’s season. With the coaching staff watching out every day, I wonder what would happen if they took the joker away.