The Cleveland Cavaliers experienced the sweet taste of victory after dispatching the Golden State Warriors in the 2016 NBA Finals. Though they finally broke that championship drought, there have been several heartbreaking moments throughout the team's history.

Fred McLeod

We'll start our sad moments in Cavaliers history with the loss of Fred McLeod. A Strongsville, Ohio native, McLeod served as the play-by-play voice of the team from 2006 to 2019. Many of his calls became instant classics. When games were close, it was “sweaty palms time.” If LeBron threw down a vicious dunk, he often made his way “right down Euclid.” And after each Cavs victory, “Freddy,” as he was known, would announce a “Wine and Gold winner.”

On June 19, 2016, the Cavs pulled off one of the greatest feats in NBA Finals history, defeating the Golden State Warriors after trailing 3-1 in the series. With the win, the team ended a 52-year championship drought for the city of Cleveland. When the final horn blew, McLeod could barely contain his emotions. Though he was on live television, Freddy cried tears of joy after seeing his team win it all:

Sadly, McLeod died suddenly on September 9, 2019 due to a heart attack. He served as an inspiration to many, and he is dearly missed.

2009 ECF loss vs. Magic

The Cavaliers made a serious run in 2009. With the top record in the Eastern Conference (66-16), expectations were running high. Fans around the globe were anticipating a Finals matchup between LeBron James and Kobe Bryant's Lakers. Sadly, it never came to fruition.

Ultimately, Dwight Howard, Hedo Turkoglu and Rashard Lewis led the Orlando Magic to victory over the Cavaliers in six games. Orlando would go on to be defeated by Kobe and the Lakers in the Finals, 4-1.

After this series, it became clear that James needed a bit more help.

Jersey strip

With LeBron leading the charge, Cleveland managed to rack up a 61-21 record in the 2009-10 regular season. This left the Cavs with the No. 1 seed in the Eastern Conference, where they would eventually lose to a Celtics team consisting of NBA greats like Paul Pierce, Kevin Garnett, Ray Allen, and Rajon Rondo (to name a few) in the semifinal round.

Many experts thought this would be the last time LeBron would take off a Cavs jersey, and it was — for a while, at least.

The Decision

Ah, yes … every Cavaliers fan knows this moment well. It was July 8, 2010, and hoops fans around the globe were glued to ESPN, anxiously awaiting LeBron's decision. Would he stay in Cleveland, or would he look for greener pastures?

In a move that sank the hearts of many Cavs fans, James announced that he would be joining the Miami Heat, where he would eventually team up with Dwyane Wade and Chris Bosh as part of their Big 3.

This move paid off for James in a big way, as he went on to claim the first two championships of his career in South Beach.

“Not one, not two, not three …”

This sad moment in Cavaliers history is directly related to James' decision to join the Heat. Sitting with his new teammates as part of an introductory press conference, the Akron native boldly claimed that Miami would win several championships in the coming seasons.

For Cavs fans who were angry with LeBron and his decision to leave Cleveland, these words were a bit of a slap to the face.

Though he didn't reach the “several” mark, James did lead the Heat to back-to-back titles in 2012 and 2013.

Michael Jordan over Craig Ehlo

There were many talented players on the Cavaliers' roster in the late '80s and early '90s, including Brad Daugherty, Mark Price, John “Hot Rod” Williams and Ron Harper. As a result, Cleveland was one of the best teams in the NBA.

Cleveland went 57-25 in the 1989 regular season, which was good for the second-best record in the Central Division standings. Notably, the Cavs had beaten Jordan and his Bulls in each of their six meetings during that campaign. However, when matched up against Chicago in the first round of the Eastern Conference Playoffs, Cleveland fell in five games.

In Game 5 of the series, Jordan knocked down one of the most iconic shots of his illustrious career. With two seconds remaining on the game clock, His Airness received an inbounds pass, then proceeded to bury a fading jumper over Craig Ehlo, giving the Bulls a one-point victory.

To this day, Jordan's shot over Ehlo is viewed as one of the greatest in NBA history. For Cavs fans, though, it was one of the saddest moments.

Making matters worse, Jordan buried the Cavs again in the second round of the 1993 playoffs, hitting a buzzer-beater in Cleveland to cap off a four-game sweep.