Not counting the years with LeBron James, winning for the Cleveland Cavaliers in the 21st century has been rare.

If we go back to 1999-2000, that would give us 22 seasons, half of which James spent on the Cavs roster. In the seasons with him, Cleveland won 560 games, while in the seasons where he played for either the Miami Heat or the Los Angeles Lakers, the Cavaliers only had 265 wins, not even half of what they achieved during the LeBron years.

Cleveland continues to search for that winning formula since James left the Cavs for the second time back in 2018, drafting Evan Mobley, Isaac Okoro, Darius Garland, and Collin Sexton in the first round of the last four drafts and making deals to acquire Jarrett Allen and now Lauri Markkanen.

Last August 28, the Cavs completed a three-team, sign-and-trade deal that allowed them to acquire Markkanen and hand him a four-year extension worth $67 million. Cleveland sent Ohio native Larry Nance Jr. to the Portland Trail Blazers, who in turn sent Derrick Jones Jr. and a lottery-protected 2022 first-round pick to the Chicago Bulls. The trade came at quite an awkward time, as the Cavaliers had just put the spotlight on Nance Jr. for their #CavsPlayerWeek program.

The Cavs have been pretty active this month as this is actually the second trade they executed. Last August 2, they sent Taurean Prince, a 2022 second-round pick via the Washington Wizards, and cash considerations to the Minnesota Timberwolves for veteran point guard Ricky Rubio. 

It thus continues to be a youth movement for Cleveland as apart from Rubio and Kevin Love, who both have played more than 10 NBA seasons, none of the other players they currently on the squad have played more than four seasons.

Apart from having a young roster, having Allen, Mobley, Love, and now Markkanen creates somewhat of a logjam in the frontcourt even with Nance Jr. gone. Mobley and Markkanen could also spend some time in the wings given their skill sets, but the two would naturally prefer to play at the 4, where Love mainly operates from as well. Allen is the only true center currently on the roster so Mobley can also take up some backup minutes when the former Texas Longhorn sits.

The Cavs could also sign another center for depth purposes and prevent Mobley from taking too much wear and tear battling the league’s bigger centers such as the likes of Joel Embiid and Deandre Ayton. Opening day is still about a month and a half away, so there’s still time to address this situation.


Love moving on could also be another development in the works. While all parties have still denied it, Love could seek a buyout if losses continue to pile on, with the likelihood increasing as the calendar flips to 2022. A trade would be much more helpful for the Cavaliers especially in the long run but the remaining $60.2 million (over two years) in Love’s contract would be harder to sell to other teams without giving up something significant such as a player from their young core or a couple of first-round picks to sweeten the deal.

On paper, the roster looks as talented as ever. Even with the apparent youth, the Cavs have the talent that could make them a more balanced squad in a few years. Summer league has shown some early promising results but the real work will begin once the season kicks in.

All signs point to Cavaliers playing the long game, given that at its current form, the team may not be able to keep up with the likes of the defending champions Milwaukee Bucks, Brooklyn Nets, Atlanta Hawks, and Philadelphia 76ers. At this point, those teams have far more star power and have been together for quite some time, so it’s an uphill climb. However, the rebuilding phase they seem to perpetually be in whenever James leaves is slowly ending and it will also depend on if Mobley and company beat their respective developmental timelines.

As a squad, they can keep games competitive and exciting (especially for the city of Cleveland) but in the meantime, they will build the game experience that will help them get over the early bumps in the road they will surely face. Biding their time, while collecting assets and experience, seems like the wiser choice for now. Nevertheless, the Cavs can still come up with some big games once in a while.

Winning has evaded the Cleveland Cavaliers for much of the past two decades, but things are looking up, especially with some of the high-potential talents they have on their roster. How they put it all together will all depend on the kind of environment the Cavs front office puts together in order for them to succeed.