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Biggest lose-lose trades in recent NBA history.

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When Charlie Sheen replaced Ashton Kutcher in Two And A Half Men, it was a lose-lose trade. There was no other way to look at it. Kutcher got dragged off his accelerating horse to A+ fame while Sheen just got dragged into rehab. Because of the behind-the-scenes antics of one person, a trade happened that fans and people involved wished they could forever unsee. Were there really any better alternatives? Maybe not. But when the tension rose, a decision was rushed and only one question loomed over everyone's heads: Could this have been done any better?

Similar to the inner working of the once most-watched comedy in America, the Philadelphia 76ers are backed into a corner with an undependable star seemingly on the way out by any means necessary. But NBA history dictates that you don't even have to go back 15 years to sense that situations like this can lead to questions like that.

Dwight Howard to the Lakers

Big Ben is sour that Doc Rivers hesitated when asked if Simmons has what it takes to be a championship-caliber point-guard (fair thing to doubt). But imagine if Ben Simmons was as direct as to say he wanted the coach fired. That's what Dwight Howard and Stan Van Gundy went through, leading to maybe the most awkward interview moment of all time. Here we had one of the most physically dominant centers since the original NBA Superman, but someone who was also criticized for not 'taking the game seriously…

After feuding with the coach and front office, with a lot of tension arising from legitimately brainless roster movers (immediately losing three starters from the finals team, signing a too-old Vince Carter then resigning a way-to-old Hedo Türkoğlu), Howard followed Steve Nash to the Lake show. Dwight never really got the hang of developing a vast arsenal of one-on-one moves (something that constantly held the entire team back in the playoffs) then feuded with just about everybody. The Magic had the worst record in the league the same season, and nine years later, might very well be the worst team next season.

Kyrie Irving to the Celtics

No matter how good of a situation you find yourself in, some people will always get distracted thinking of the negatives. Kyrie Irving was on a winning team, but it wasn't his team, something that he obviously could never get past. So without any notice to LeBron, Kyrie forced his way out and got quickly traded for Isaiah Thomas. A less talented player coming off a hip injury sounds like a great idea. The Cavaliers just wanted a reliable offensive running buddy for LeBron, and the Celtics wanted a championship leader to foster the development of their young stars. Neither got what they wanted.

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Instead, I.T became a more brittle version of an old Derrick Rose, forcing him to have to be again traded to the Lakers so Cleveland could still compete before LeBron inevitably left (literally, he played 89 fewer games from 2018-21). Kyrie misses the entirety of his first playoffs where his supporting cast actually overachieves. With Kyrie back the following year, the youthful momentum had clearly staggered, concluding with their 'leader' quitting on them and the fan base midway through the Bucks series. Kyrie realizes leading a team is not his forte and becomes the third option on a soon-to-be-guaranteed ring - that's if Kyrie actually even plays.

Deron Williams to the Nets.

Simmons might have been called the next LeBron James, but once upon a time, Deron Williams was thought to be the next Jason Kidd and was even neck-and-neck with a young Chris Paul. But for those that started watching basketball from 2014 onwards, that's like saying Patrick Williams was Scottie Pippen 2.0. Drafted to a 26-56 Utah Jazz, Williams (Deron Williams that is) dragged the Jazz to a 51-31 record by his sophomore season and even went as far as the Western Conference Finals the same year. But after losing to the Lakers three years in a row and one giant fight mid-game with head coach Jerry Sloan about his adherence to the plays, Sloan retired the next morning.

Just like that in the middle of the season, the Utah Jazz lost their head coach for over 20 years and their franchise point guard to the Brooklyn Nets a few weeks later. The best the Jazz were able to scrape up after the ordeal was Devin Harris, Derrick Favours, and a pick that landed them Enes Kanter. Not exactly an even trade.

In New Jersey, however, the trade didn't look horrible, at least initially. But the cracks on the ceiling started to emerge when head coach Avery Johnson was fired in the middle of December in 2012, after just winning Coach Of The Month. I wonder who would have played a part in that? Sidenote: The Net's original plan was to pair Williams up with Carmelo Anthony; since he made it public, he was locked in on New York. So can you imagine the two biggest' coach combatants' on the same team?

Anyway, the Williams decline in play seemed to correlate with Brooklyn's front office malfeasance. Trading for Gerrald Wallace in exchange for a first-round pick to Portland that turned out to be Damien Lillard was pretty rough. But after the infamous 'Boston Trade' in the offseason of 2013 - sending four first-round picks for three ex-stars ten years past their prime - the entire franchise became brutally trapped for half a decade. Williams went from franchise player to role player to one of the worst contracts in the league two seasons later.

All of these examples had three things in common. 1. A diva-like star that feuded with either the coach or a particular player. 2. A front office that rushed their departure and came up short. 3. A realization on the other end that internal problems don't just disappear with a jersey swap, especially ones that appear off the court. The Simmons dilemma is unique since he is under contract for four more seasons, and forcing him to join the locker room again from the threat of fines might not go ultra-smooth. But it's a whole level better option than giving the All-NBA 25-year old away for D'Angelo Russell and some picks.

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