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5 Most Heartbreaking NBA Deals of All Time

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Kevin Garnett of the Boston Celtics celebrates after defeating his former team of twelve years, the Minnesota Timberwolves in Boston, Massachusetts. (Photo by Brian Babineau/NBAE via Getty Images)

Kevin Garnett of the Boston Celtics celebrates after defeating his former team of twelve years, the Minnesota Timberwolves in Boston, Massachusetts. (Photo by Brian Babineau/NBAE via Getty Images)

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WASHINGTON (CBSDC) – The NBA has a rich history of witnessing head-scratching deals at the deadline and summer free agency acquisitions, which have left entire fanbases dumping their most beloved hero’s jersey into the nearest garbage receptacle.

Some of such heartbreaking deals are made by the doing of the team, but many are the doing of the player’s backroom kvetching, or the more transparent result of a player signing freely elsewhere in search of a championship and/or a massive payday.

No matter the reason, the end result is always the same: the gripping reality of a fiercely emotional heartstring now severed.

And there is always a clear winner and loser.

These are the Top 5 Most Heartbreaking NBA Deals in NBA History:

5. Pau Gasol Traded from Memphis to LA

Perhaps the least egregious of the deals you’ll find on this list, in Feb. 2008, the Memphis Grizzlies struck a deadline deal to send perennial All-Star Pau Gasol, along with a second-round pick, to the Los Angeles Lakers in exchange for Kwame Brown, Javaris Crittendon, Aaron McKie and the draft rights to Gasol’s younger brother Marc, as well as first-round picks in 2008 and 2010.

On the surface, it seems like a fair deal. But consider the ramifications: The Lakers would make three consecutive NBA Finals appearances (2007-08, 2008-09, 2009-10), winning the latter two. The Grizzlies have not done that.

4. Charles Barkley Traded from 76ers to Suns

In June 1992, the Philadelphia 76ers traded six-time NBA All-Star Charles Barkley to the Phoenix Suns, for Jeff Hornacek, Tim Perry and Andrew Lang, in a “move bound to have drastic impact on the franchise,” as Clifton Brown wrote at the time.

Barkley, after losing teammates Moses Malone and Julius Erving in consecutive seasons, had been pressuring the organization to surround him with more talent, specifically a center as the team had cycled through 13 different options to secure the post following Malone’s departure to Washington.

The year before trading Barkley, the 76ers signed center Charles Shackleford, who had been playing in Italy, in an attempt to placate Barkley, who famously responded, “I told them I wanted Shaq. They got me Charles Shackleford.”

The next season Barkley was off to the rising Suns in Phoenix.

Philadelphia would record a cumulative record of 93-235 over the next four seasons.

3. Shaquille O’Neal Leaves Magic to Sign with Lakers

In July 1996, Shaquille O’Neal cut a $120-million deal with the Los Angeles Lakers, thrusting his former team, the Orlando Magic, into years of middling obscurity. The day before a deal was struck, the Orlando Sentinel ran a poll asking one simple question: “Is Shaquille O’Neal worth $115 million over seven seasons?” The results echoed an overwhelming (91.3%) ‘No.’

O’Neal, who’d also received a less-than impressive offer from the Magic, took notice of the poll results.

“Not the type of thing that you want to come out on the day that your franchise player is about to sign or not re-sign,” said then Magic vice president for basketball ops and player personnel, via the LA Times. “I really wonder why that came out on the day it did. I wanted to call to find out why, but I didn’t really want to ask the question. Shaq is a kid who wanted to be accepted and appreciated. Maybe it’s a factor. I don’t know.”

Years later, Shaq was asked by Mike Bianchi whether the catalyst for him departing Orlando was that Sentinel poll, the Magic’s initial offer, or his desire to be a star in a big city. Shaq’s response:

“Forty percent of it was the Sentinel poll and the fact that I was very sensitive at a young age. Ten percent of it was that Bob (Magic president Bob Vander Weide) and the organization didn’t move quickly enough (to match the Lakers’ offer).”

Shaq would go on to win three championships with the Lakers, and later, one with the Heat. After making the NBA Finals and Easter Conference Finals in consecutive seasons with O’Neal, without him, it would be twelve years until the Magic would advance past the first round of the playoffs.

2. Kevin Garnett Traded to Boston to Form Big Three

At 6-foot-11, 220 pounds, in selecting Kevin Garnett out of high school with the 5th overall pick in the 1995 NBA Draft, the Minnesota Timberwolves acquired that rare blend of height, speed, power, agility and range. The Big Ticket would make 10 All-Star appearances over the next 12 seasons, leading Minnesota to 8 playoff appearances, where the Timberwolves wouldn’t advance out of the first round but once, in 2003-04.

In August 2007, after missing the playoffs altogether for three straight years, general manager Kevin McHale decided to pull the plug, sweethearting a deal with his former Celtics teammate, (Boston GM) Danny Ainge, to send Garnett to Boston, forming the Big Three of Garnett, Ray Allen and Paul Pierce.

In exchange, the Timberwolves received Al Jefferson, Ryan Gomes, Gerald Green, Sebastian Telfair, Theo Ratliff, two first-round picks and cash considerations.

Boston would win the NBA Championship that very season in 2007-08, and make another NBA Finals appearance, which they would lose to the Lakers, two years later in 2009-10. Minnesota hasn’t so much as had a winning season in the seven years since.

1. The Decision: LeBron James Chooses Miami

Perhaps the only transaction on this list which requires little to no research, LeBron James’ decision to stab a knife in the hearts of the fans of Cleveland — where he spent his first seven seasons, won two MVPs, made one failed NBA Finals appearance and essentially salvaged a previously wrecked franchise from the junkyard of NBA nothingness — will stand the test of time as one of the most colossal and heavily orchestrated failures by a player to inform his team and departing city of his decision to pursue championships elsewhere, with tact and respect to the fans, as there ever will be.

It wasn’t the decision in itself to leave which projectile vomited Lebron from hero to instant-villain, it was manner in which it was done, holding Cavs fans hostage for weeks, making them think they had a chance to retain their free agent franchise player, only to watch him inform the nation, on ESPN of all outlets, he was taking the other gal to the dance, in the most grandiose, embarrassing way possible, or, in his words, “I’m gonna take my talents to south beach and join the Miami Heat.”

The utter lack of regard for fan emotion is one thing, but consider James was viewed, at the time, as Cleveland’s savior, a franchise which never in its 40-year history had so much as sniffed a championship before his arrival, and then, he was leaving because he felt “this is gonna give me the best opportunity to win.”

Two days later, James was at the American Airlines Arena, declaring in front of a raucous sellout Miami crowd, alongside the latter thirds of the NBA’s new Big Three — Dwyane Wade and Chris Bosh — their intentions to win not one NBA Championship, not even two, “not three, not four, not five, not six, not seven…”

Cavaliers fans trashed and burned James jerseys, and their rightful outrage could only be outmatched by team owner Dan Gilbert’s, whose probably regretful letter posted to the team’s website the next day will live in infamy. Of it, there are so many highlights, but here’s one excerpt which perhaps captures the emotion, and the message, the best:

“This shocking act of disloyalty from our home grown ‘chosen one’ sends the exact opposite lesson of what we would want our children to learn. And ‘who’ we would want them to grow-up to become.”

The Big Three would go on to make four consecutive NBA Finals appearances, winning the middle two. Over the last four years combined, Cleveland has a record of 97-215 (.311). But alas, there’s still hope.

Note to readers: The only player on this list not to go on and win a championship is Charles Barkley, but then again, neither have the 76ers.

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