How the Cleveland Cavaliers’ perimeter defense will be tested by Damian Lillard and the Bucks

The Eastern Conference has become much more daunting for the Cleveland Cavaliers now that Damian Lillard is in Milwaukee. There is no way that he doesn’t change how the two teams matchup.

The Cavs, over the past few seasons, have a winning record against Milwaukee. Dating back to the 2021-22 NBA season, the Cavaliers hold a 5-3 record in the regular season versus the Bucks. Four of those victories came by double digits. Though it’s worth noting that Giannis Antetokounmpo was absent in three of those wins for Cleveland.

Cleveland has still managed to survive even when Giannis is steamrolling them – such as one game from last season when Antetokounmpo posted 45 points and 14 rebounds in a losing effort for Milwaukee.

Much of Cleveland’s recent success against the Bucks can be credited to timely support from their role players. Cedi Osman and/or Kevin Love led the Cavaliers in scoring in three of the five victories versus the Bucks. In another win, Evan Mobely posted a career-high 38 points. These big performances have allowed Cleveland to prevail over the Eastern Conference’s top dog.

On the defensive end, the Cavaliers managed to contain the Bucks primarily by stopping Jrue Holiday. Isaac Okoro was particularly successful against Holiday, holding him to 3-12 shooting behind a gritty defensive showing in December 2022. Overall, Holiday has shot 30-76 (39%) against Cleveland since 2021.

Okoro, who is probably Cleveland’s best perimeter defender, found success against Holiday by limiting his opportunities in the paint and forcing him into difficult mid-range jump shots.

With Holiday gone and Lillard entering the picture, how does this matchup change for Cleveland? It’s possible Lillard’s arrival not only makes covering the point-of-attack more difficult, but makes protecting the paint is a whole new burden, as well.

Lillard is a more prolific scorer than Holiday. He has been rivaled by only Stephen Curry in terms of pull-up three-point shooting over the last 10 years. He drilled 159 pull-up threes last season, leading the entire NBA despite playing just 58 games played.

Teams can go under screens against Holiday. Teams cannot against Lillard.

By being a threat to shoot the ball from anywhere, Lillard will stretch the floor for Milwaukee in a way Holiday could not. Forcing the defense to play much further out will put a heavy strain on whoever is tasked with defending Dame on the perimeter. And in doing so, there will be more space for the freight train that is Giannis.

These two operating a pick-and-roll will be a nightmare for NBA defenses. And while the Cavaliers are as equipped as anyone to protect the paint, this is still an area of concern — as Giannis running downhill should concern anybody.

The other question is Cleveland’s perimeter defense with Max Strus expected to replace Okoro in the starting lineup. This puts a potential chink in the Cavaliers’ armor as so much of their top-ranked defense last year was dependent on Okoro’s ball-stopping prowess. Up to this point, Strus has only ever been deemed an average perimeter defender, at best.

It’s likely the Cavs will be forced to rely on the rim protection ability of Mobley and Allen to cover for the limited defensive trio of Strus, Garland and Mitchell. Assuming Okoro is still in the rotation to some degree, even he will have his hands full against a high-volume scorer in Lillard.

While Mobley and Allen are more than capable of anchoring a defense, over-extending them to shield the perimeter has burned Cleveland from behind the three-point line in the past. Specifically against Milwaukee, where Bobby Portis and Brook Lopez have torched them from deep when Cleveland’s bigs step up to deter a drive.

Portis made five three-pointers in the first half of this game as Cleveland prioritized stopping the ball-handler from getting into the paint.

This hyper fixation on plugging up drives led to Portis being wide open over and over again.

It’s easy to see how Lillard’s arrival will further exacerbate this problem. He is an even greater threat to shoot over screens or drive to the basket himself. Lillard acting as the ball-handler, with Giannis screening and catching with kick-out options on the perimeter will be a tough action to defend. Especially considering Giannis is a quality decision-maker with the ball.

Combining the three-point shooting prowess of Lillard with the lethal slashing ability of Antetokounmpo is a match made in heaven and a clear upgrade over Holiday (who was a respectable scorer in his own right). However, the concern remains – what kind of defensive limitations will Lillard bring to Milwaukee?

Holiday is a five-time member of the NBA’s All-Defensive team, serving as the Bucks’ backbone at the point of attack. Dame, on the other hand, has never been praised for his defensive capabilities.

While defending Lillard will be a challenge for Cleveland, the flip side is a new obstacle for Milwaukee. Donovan Mitchell and Darius Garland form an electric backcourt pairing and Lillard will be an easy target in a potential playoff series.

Funnily enough, this is where we start to see some similarities between the Cavs and the Bucks. Both teams are vulnerable on the perimeter defensively. Yet, both squads have supreme help-defenders in Allen and Mobley for Cleveland, then Antetokounmpo and Lopez for Milwaukee.

This makes a hypothetical postseason matchup between the two an exciting one to consider. They are built to test each other’s greatest weaknesses and the stage for a battle of the stars can certainly be set.

Nonetheless, Milwaukee’s superstar duo is smack dab in the middle of its prime. Giannis is 28 years old while Lillard is a bit older at 33. Meanwhile, the Cavs are still banking on the long-term development of Mobley (22) and Garland (23). This, along with their not-so-inspiring collapse in last year’s playoffs, has me feeling like the Cavaliers are simply not in the same tier as Milwaukee.

Still, the on-paper matchup is a fun one and it will be a blast watching Cleveland (and the rest of the NBA) scramble to defend the league’s newest juggernaut.