How could the Cavs improve? By adding a quality wing, but that won't be easy

If there were any remaining questions regarding the 25-14 Cavaliers’ legitimacy in this year’s loaded Eastern Conference, perhaps Donovan Mitchell’s 71-point outburst on Monday crystallized the level of talent Koby Altman’s front office has assembled in Cleveland.

Mitchell has been worth every penny, including access to all five of Cleveland’s future first-round picks through 2025-29 that the Utah Jazz commanded in return for the All-Star guard. He and Darius Garland have formed one of the more potent backcourts in the NBA, both able to punish defenses off the dribble and off the catch. The combination of Jarrett Allen and Evan Mobley up front has struck fear in countless challengers at the rim.

There is one obvious positional upgrade on the wing that has been staring at Cleveland decision-makers for some time. The Cavaliers sent Ricky Rubio and a protected first-round pick to acquire Caris LeVert at last year’s trade deadline. But with Mitchell now in the fold, it’s no secret around the league that a defensive-minded stopper who’s a consistent shooting threat stands as Cleveland’s true missing piece.

There is, however, no clear answer for this thought experiment. The Cavs’ expunged virtually all their draft capital of this decade to acquire Mitchell and LeVert, and won’t be able to move their 2024 first-rounder until the night of next year’s NBA draft. If Cleveland pinpointed a specific veteran on a significant salary, such as Houston's Eric Gordon, the Cavs would need to either send LeVert and another rotational player out the door — a far higher price, sources told Yahoo Sports, than Cleveland officials have the appetite for. To be clear: Gordon is not a trade target.

The Cavaliers fit the exact makeup of a team that would swallow Tobias Harris’ hefty salary in favor of his two-way effectiveness, but there’s no outgoing package from Cleveland that would likely entice Philadelphia, especially with Harris’ dynamic production this season in a more complementary role alongside James Harden’s pick-and-roll activity.

A smaller salary player, such as Jae Crowder, would seem to make sense on the surface, although Phoenix has stood its ground on Crowder, sources said, demanding a playoff-caliber player in return. If the Cavaliers had one available on the roster, this Cleveland discussion wouldn’t exist. The Cavs have never been linked to the disgruntled Suns forward, and Cleveland’s growing salary bill will further force the small-market Cavaliers to spend wisely on whichever extensions they do ultimately doll out to contributing rotation players.

Crowder, remember, is seeking a multi-year extension along the lines of PJ Tucker’s recent three-year, $33 million deal with the Sixers. And LeVert, for example, never had true extension conversations this summer, sources said, after injury limited his availability to just 19 games following last February’s trade.

Chalking up LeVert as a definitive trade candidate, though, is not so simple either, even with the 28-year-old set to reach free agency this summer. LeVert represented Cleveland’s primary trade target last season, and the Cavaliers value his high-character presence in the locker room. While his secondary ball-handling opportunities have dwindled since acquiring Mitchell, he has proven invaluable as a creator when either Garland or Mitchell has missed time. The Cavaliers do appear open to discussing LeVert, but moving him now would come at far lower value than the first-round pick and multiple second-rounders Indiana netted for his services a season ago. When Cleveland evaluates potential deadline acquisitions, LeVert will be the comparative barometer as to how much any possible starting-level addition moves the needle.

The other in-house options on the wing have delivered mixed results. Lamar Stevens brings tenacity, strength and athleticism, and has been excellent cutting through defensive holes, but the Cavaliers’ could stand for a far greater threat from distance than Stevens’ 29.8% clip this year. Big forward Dean Wade is not a natural three-man in today’s league, yet Cleveland had found success with Wade (41.1% from three) — when healthy — masquerading as Lauri Markkanen from a season ago. Wade is tracking toward a return from a sprained AC joint and has not played since Dec. 2.

In a perfect world, Isaac Okoro, the No. 5 pick in the 2020 NBA draft, would emerge as the Cavaliers’ homegrown solution on the perimeter. Knicks officials were bracing for Cleveland to select Obi Toppin fifth in that draft, sources said, before the Cavs surprised several rivals by choosing Okoro out of Auburn. He flashed promise in the preseason, knocking down 42.9% of his triples in exhibition play, but is connecting on a career-worst 26% of his 3-pointers this year, even opening the season 0-of-12 from beyond the arc.

The Cavaliers, though, are still holding onto a belief Okoro can develop into the swingman of their present and future. He is considered a diligent worker, and Okoro has a strong desire to remain in Cleveland, sources told Yahoo Sports, to continue growing around the young core this front office has assembled. The question remains: How long will the Cavs be willing to watch his progression unfold, especially as he enters the final year of his rookie deal next season?

Add in Cedi Osman, and Cleveland has a stockpile of rangy wings that can be effective, but leave something to be desired. Are any of them the talented young player Detroit is partly searching for to offload Bojan Bogdanovic? The Cavaliers are indeed a Bogdanovic suitor, sources said, but it will be rather difficult, and perhaps impossible, for Cleveland to reach Detroit’s lofty asking price for the veteran sharpshooter.

At this juncture, the Pistons are seeking at least one first-rounder and either a young player with upside or additional draft capital, sources said, plus Cleveland has company in Dallas, Phoenix and the Lakers, among other teams in pursuit of Bogdanovic. Saddiq Bey would be another interesting addition for Cleveland and on a similar timeline as the rest of the team’s core pieces, yet the same cost issues will apply in that approach as well.

Kelly Oubre marked an intriguing name for the Cavaliers before the Hornets forward opted to undergo surgery on a torn ligament in his left hand that will now sideline him for four to six weeks. Any playoff team looking for reinforcements will likely hesitate and search for more of a certainty on the trade market before pursuing a player on the mend. Could the Cavs pry Jalen McDaniels from Charlotte? And would McDaniels really raise Cleveland's ceiling? Elsewhere in Charlotte, P.J. Washington is set for free agency this summer as well, but presents more versatility in the frontcourt than the wing for Cleveland. And while he's not a target for the Cavs, Mason Plumlee would seem the most likely Hornets trade piece ahead of the Feb. 9 deadline with the recent emergence of lottery pick Mark Williams, even with Plumlee owed a $1.66 million trade kicker if moved.

There won’t be many players filling the Cavaliers’ wish list from true contending teams. That would leave theoretical targets such as Josh Richardson from San Antonio or perhaps Gary Harris and Terrence Ross from Orlando, all playing without guaranteed money for 2023-24.

Cleveland has no cause to rush forward with its approach. But like the Clippers’ known interest in a switchable big, the Cavaliers’ search for wing improvements ahead of the trade deadline has been a consistent item among front office discussions this season.