When we start talking about some of the top Cleveland Cavaliers seasons of all time, you probably hadn’t had this current Wine and Gold squad in mind but as we reflect back on this Cavs season and consider what an impressive run it’s been to this point, it really is something to “witness.”
Speaking of “witness”, when you hear that you then think about LeBron James and being a “witness to his greatness” and all the things he did for Cleveland in those great years he played for the Cavs.
We now though in Cleveland have transitioned to another era in Cavs basketball, one that has every sign of lasting a long time. Though I’m still not sold on their head coach J.B. Bickerstaff, who I don’t believe can coach this team to an NBA title, I will admit the last two seasons and the momentum you can feel growing bigger by the second these days are all very impressive.
So, without ado, here, we’ll highlight the five best Cavaliers seasons ever.
The fifth-best Cavs season all-time: This season
So where do we see this season in the grand scheme of things? It now has made it’s way into the top 5 seasons of all-time. When you start reviewing other seasons in Cavs history, you now have to start putting this team in that top discussion. Granted that the Cavs, led by James in the past made it to several more championship series, but they only won the one title.
With the rise of this current team and the overall excitement it has brought to the fans of the Wine and Gold, you have to give it the No. 5 slot in my mind. The addition of guard and superstar Donovan Mitchell has amplified everything this year and like when the Cavaliers used to have James, when Mitchell is on the court, you always have a feeling that the Cavs can win.
Beyond Mitchell’s addition, the rest of the core players including Evan Mobley, Jarrett Allen and Darius Garland are all helping create a team that will be around and competing for titles for the foreseeable future. They are all so young, all in their early 20’s and getting better with every dribble of the ball. For now, this season is our first of five great Cavs seasons. Let’s look at No. 4 next.

The fourth-best Cavs season: 2006-07
The Cavs were starting to build a winner behind the play of a young LeBron James. Mike Brown was the head coach and the team ended up going 50-32 and managed to work their way into the NBA Championship where they played the far more experienced and veteran team in the San Antonio Spurs.
LeBron and his Cavs got swept but at the time you thought you’d be seeing Cleveland back in the Finals the next season. That didn’t happen and instead, a couple seasons later James was off to Miami Beach.
However, while they were in this season, the Cavs were unstoppable until the very end. In the playoffs they ran by the Washington Wizards in the first round. Then they got challenged by the New Jersey Nets before winning the series and then they had to play their nemesis in the Detroit Pistons. They were the team in the East to beat and Cleveland had their chance in this epic battle.
It took the Cavaliers and James having a historic performance in a Game 5 double overtime win to really secure the series and a chance in the NBA Finals. In this monumental performance James was unstoppable, going for 48 points and scoring pretty much every point as the game got to the end. Cleveland had finally made it to the top.

The third-best Cavs season: 1988-89
We head back in time to when the Cavs had their run of great teams led by Mark Price, Brad Daugherty, Larry Nance Sr., Ron Harper and “Hot Rod” Williams. This 1988-89 season was something special, or so we thought.
They finished the regular season at 57-25 and had an opening round of the playoffs matched up against the Chicago Bulls. While the Bulls had a young Michael Jordan, the Cleveland squad had some solid players like Price and Daugherty. Certainly, they would be able to get by the Bulls.
However, the series was tight throughout. We didn’t know it at the time, but Jordan was becoming the greatest of all time and that got a big boost when he made “The Shot”. That was back when the first round series was a five-gamer. Cleveland lost their first home playoff game to start the series and that set the stage for the epic Game 5.
Unfortunately, that game is now labeled as “The Shot” because Jordan nailed a jumper at the buzzer to give the Bulls the upset win. That play still haunts most Cleveland fans today.
It was though the beginning of a run of really good Cavs teams that were playoff bound and ready to win a title. Unfortunately, Michael Jordan existed and that was the kryptonite to the Cavaliers.

The second-best Cavs season: 1991-92
When we got to the 1991-92 Cleveland season, the team was ready to roll and finally get by the Chicago Bulls. Unfortunately, that didn’t happen as again Jordan stood in between the championship and the Cavs. As I said before, the Cavs might be gloating about two or three titles if it weren’t for Jordan. He had so much influence on the game 30 or so years ago.
When there is this debate about who is better between LeBron James and Michael Jordan, most young fans side with James. But if you’re older, then you know that Jordan was then superior to his influence on his team’s success in comparison to James. The six championships that Jordan has will always be more impressive than whatever James does.
That type of power that Jordan had back then was the biggest blockade to the Cavs. Even though Cleveland had another fantastic team, they couldn’t get over the final hurdle. That season, they rolled into the playoffs again with a 57-25 record. They got by the then-New Jersey Nets and then beat the Boston Celtics in a seven-game series. That lengthy series with the Celtics likely took a toll on the Cavaliers and then didn’t have much of a chance against Chicago where they lost in six.

The best Cavs season: 2015-16
We finally have made it to the best Cavs season to date and you have to go with that spectacular 2016 year. James had come back to Cleveland in the summer of 2014 and immediately made the Cavaliers relevant again and took the team to the championship in the previous season in 2015. They lost to the Golden State Warriors. Little did we know then that these two squads would battle it out in the championship series over the next four seasons.
While the Wine and Gold lost in three of those matchups, the one title they did win in 2016 will likely be the best moment in Cavs history. The fact that Cleveland was able to climb back into that title series, where they trailed 3-1, is really something special.
In Game 5 of that series, both James and Kyrie Irving scored 40-plus points on the road. It was epic and that momentum led them to a home win in Game 6. This all leads us to huge Game 7 where James had the block of his career and Irving knocked down the biggest three-pointer in his career. It was the first and only time in NBA Finals history that a team came back from a 3-1 deficit.
It is and will continue to be the top Cavs season of all-time. That is until these new young Cavaliers win their first title.
Could it happen this season? Why not!

