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Ranking Orlando Magic moments that made us cry

The most devastating, tear-inducing moments in Magic history

Tracy McGrady and Doc Rivers after Game 7 loss Photo by Allen Einstein/NBAE via Getty Images

Who’s choppin’ onions in here?

As part of SB Nation’s “Sports Moments That Made You Cry” theme week, we decided to rank the Orlando Magic’s most devastating, tear-inducing moments. It could be a crushing loss, a trade gone wrong, a poor free agent signing, or simply a humiliating moment for the organization and fan base.

Before we get to the top 10, here are some honorable mentions. If I forgot any (perhaps they are simply blocked from memory), feel free to share below.

Honorable Mention: Grant Hill and Penny Hardaway injuries, Bismack Biyombo and Jeff Green signings, the 2030 guarantee, Fran Vasquez and Mario Hezonja draft picks, the T-Mac and Gilbert Arenas trades, the Shelvin Mack assists graphic, the entire Rob Hennigan era.

And now for the top 10. Brace yourselves.

10. The Whiteboard

Tears of embarrassment. Letting the NBA world, and your perceived franchise players, know your offseason plans during a photo mishap was just a humiliating moment during an already dark period.

9. Tobias Harris and Victor Oladipo trades

Toronto at Orlando Stephen M. Dowell/Orlando Sentinel/Tribune News Service via Getty Images

It’s been difficult not to tear-up over the last few seasons while watching Oladipo and Tobias play. True, we’ll never know if they would have developed while surrounded by the Magic’s personnel, but seeing them prosper as All-Star caliber talents on other teams has been torture (although Magic fans are happy for both of them, of course). Knowing how little the Magic received in return makes it even worse.

8. LeBron’s buzzer-beater

Looking back now, no harm done. But in the moment, LeBron’s game-winning three-point heave at the buzzer in Game 2 of the 2009 Eastern Conference Finals seemingly cost the Magic a trip to the NBA Finals. It was as crushing of a loss as I can remember. The Magic persevered. Still, in areas other than Central Florida, the shot overshadows the Magic’s series win.

7. The end of the “Heart & Hustle” Magic

Darrell Armstrong and Doc Rivers

A team that was expected to win a handful of games after a full rebuild found itself battling for a playoff spot in Game 81. Facing the Milwaukee Bucks in a matchup that would essentially determine the eighth seed in the East, the Magic trailed by two when Chucky Atkins missed a go-ahead three in the closing seconds, bringing an end to the season for the beloved “Heart & Hustle” Orlando Magic.

6. The Dwightmare

By the time the Magic finally traded Dwight Howard to the Lakers, it was mostly tears of joy. It brought relief, ending the months-long public saga known as Dwightmare, which was highlighted by the infamous and cringe-worthy interview where Dwight crashed Stan Van Gundy’s media session moments after SVG said Howard wanted him fired. But at the same time, the trade ended what was arguably the Magic’s greatest chapter, with a conclusion that reopened old wounds and brought back memories of Shaq’s departure. The Magic were like the Lakers’ minor league affiliate, developing Hall of Fame centers until they were ready to play out their prime years in the big leagues of L.A. Didn’t work out this time around for the Lakers. As for the Magic, last season they finally made the playoffs in the post-Dwight era, but since he left, there have been a lot more tears than cheers in Orlando.

5. “It feels good to get in the second round.”

Tracy McGrady and Doc Rivers after Game 7 loss Photo by Allen Einstein/NBAE via Getty Images

Tracy McGrady and the Magic went up 3-1 on the Detroit Pistons in the first round of the 2003 playoffs, putting them one victory away from being a rare eight seed to topple a one seed. T-Mac at his postgame presser prematurely began to talk about the second round, uttering the now infamous quote of “It feels good to get in the second round.” The Magic lost by 31 in Game 5, they lost by 15 on their home court in Game 6, and then by 15 again in Detroit in Game 7. The Magic became just the seventh team in NBA history to blow a 3-1 series lead. Oh, and this was the first postseason that the NBA extended the first round series from best-of-five to best-of-seven.

4. Courtney Lee’s missed layup

NBA Finals Game 2: Orlando Magic v Los Angeles Lakers Photo by Noah Graham/NBAE via Getty Images

No words needed.

One of the ultimate tearjerkers…

3. Game 1 of the 1995 NBA Finals

The Magic blew a big lead. Nick Anderson missed four straight free throws. Kenny Smith hit a record number of threes, one of which was in the final seconds of regulation to force OT. Hakeem Olajuwon converted an impressive game-winning tip-in in overtime. If just one of those things doesn’t happen, there’s a good chance the history of the Orlando Magic looks quite different today. Instead, the Magic got swept in the NBA Finals.

2. Collapse in Game 4 of the 2009 NBA Finals

The Magic were up five against the Lakers in Game 4 of the NBA Finals, less than a minute away from evening the series at 2-2. Kobe Bryant made an incredible pass to Pau Gasol in the lane for an easy dunk that cut the lead to three. Dwight Howard missed a pair of free throws when one would have sealed the win. Stan Van Gundy decided to 1) pressure the ball in the backcourt and 2) leave the still-not-fully-recovered Jameer Nelson in the game for the final defensive sequence. Nelson failed to cut off Derek Fisher, and Fisher hit a game-tying three to send the game to overtime. The Magic lost in overtime. The thought of how easily the Magic could have been up 3-1 in this series will make you cry yourself to sleep.

1. Farewell, Shaq

Shaquille O’Neal signs with the Los Angeles Lakers Press Conference Photo by Andrew D. Bernstein/NBAE via Getty Images

For a young child like me at the time, this was my first experience with heartbreak. The Magic had the pieces in place to compete for a championship for the next decade. Shaq and Penny should have been what Shaq and Kobe became. But in July of 1996, Shaq signed with the Lakers, altering the course of history for the Orlando Magic. Was it because of he became jealous of Penny’s stardom? Was it his feuding with coach Brian Hill? That silly poll in the Orlando Sentinel about how much Shaq was worth? His Hollywood ambitions? Probably all of the above. I’d say that Shaq leaving Orlando still stands as the most crippling free agent defection in the history of the NBA. At least LeBron returned to Cleveland and won a title.