It's been quite the turnaround in the 2021 season for the New York Knicks. After one miserable year followed another, Tom Thibodeau's bunch has completely flipped the script and the energy around New York.

Before Thibodeau's arrival, and aside from the constant losing, dysfunction and chaos seemed to be the only thing going on in the Big Apple. To simply put it, the once-proud Knickerbockers had become the laughing stock of the entire league.

A big chunk of the disaster stemmed from its management, as James Dolan had and still is undoubtedly one of the most disliked owners in all of sports. But the attention on Dolan has faded away during this successful run for the Knicks in 2021.

The Knicks appeared cursed at times and yet new GM Leon Rose has started the process of steering this franchise back in the right direction.

It obviously hasn't always been all roses and fairytales for the New York Knicks, though. And because of that, we have this list.

Let's recall five of the most heartbreaking moments in Knicks' history.

The treatment of Spike Lee 

Most heartbreaking moments in New York Knicks history

For as long as people can remember, Spike Lee has remained as the lone constant at Madison Square Garden. The 63-year-old film director has been attending Knicks games for the last 29 years and has remained a loyal supporter throughout the hard times.

In 2020, Lee announced that he would no longer be present at home games that season after reportedly being harassed by the team owner and his team of goons. What makes this whole debacle ridiculous is the fact that it started over something as trivial as using an entrance to the arena.

You read that right. James Dolan appeared willing to burn bridges with their most beloved figure over a freaking entrance.

Lee has been the epitome of a super fan. He's loud and loyal to a fault. The Knicks definitely appeared to have done wrong in this scenario from 2020. Spike Lee, of all people, does not deserve to be treated like that after years of dedication he gave to New York.

The departure of Pat Riley

This still goes down as one of the biggest “What ifs?” in basketball. The Knicks were simply never the same after Pat Riley resigned as the Knicks head coach (through fax) in 1995 and accepted a president and head coaching gig with the Miami Heat.

Considering the success of the Heat franchise since Riley took over their front office, pundits are left wondering if New York could have been the one basking in the limelight if only the brilliant basketball mind stayed put.

The Knicks were perennial contenders under Riley from 1991 to 1995. They still managed to win under Jeff Van Gundy in the ensuing seasons, but maybe things could have turned out differently under Riley's continued guidance.

Charles Smith's missed and blocked layups vs Bulls

To be fair, Knicks players do have a history of clunking easy layups. Even their Hall of Famer Patrick Ewing was once chastised for missing a point-blank shot that could have given them the W against the Indiana Pacers in the 1995 playoffs.

But as far as the biggest gaffe goes, Charles Smith takes the trophy on this one. The 6-foot-10 forward had plenty of chances to give the Knicks the lead against their rivals, the Chicago Bulls, in Game 4 of the 1993 Eastern Conference Finals. Instead, he notoriously flubbed four consecutive attempts as the Bulls went on to win the game and ultimately, the series.

The Bulls stifling defense certainly deserves credit for this one, but that was just truly painful to watch.

Reggie Miller goes berserk in MSG

Spike Lee makes this list twice, although he certainly shoulders the blame on this one. Lee's big mouth gave opposing player Reggie Miller some extra inspiration to torch the Knicks in the 1995 playoffs.

With the Knicks up 70-58 entering the final frame, Lee continuously taunted the legendary Pacers shooting guard for most of the game. Miller responded by dropping 25 points in the fourth quarter — scoring nine points in a span of 11 seconds to complete the comeback win.

That iconic moment gave birth to the now-infamous “choke gesture”. The sight of crazy-eyed Reggie Miller going bananas in the Garden still gives Knicks fans nightmares to this day.

John Starks' disappearing act in 1994 Finals

With Michael Jordan out of the picture in 1994, the Knicks were primed to win their third championship in franchise history. All they needed was to win just one game against the Houston Rockets. With New York up 3-2 in the series, Houston forced a Game 7 at Madison Square Garden after Hakeem Olajuwon rejected John Starks' game-winning 3-pointer attempt.

Starks was having a phenomenal season that year but was extremely unreliable when they needed him the most. He had arguably the worst game of his pro-career in Game 7 after going 2-for-18 from the field. Making things worst, the 6-foot-3 guard went 1-for-10 in the fourth quarter.

Things are looking up for the Knicks and their franchise. But every team, including New York has those memories stored away that will break your heart. These are the most heartbreaking moments in New York Knicks history.