The 23 Biggest Fails of Michael Jordan's Career

Image via Complex Original

Date: 1988-1990

Jordan's overall playoff record is obviously sparkling, but it wasn't always that way. In the early stages of his career, he simply could not handle the Bad Boy Pistons and their "Jordan Rules," falling to them three years in a row. Detroit would absolutely brutalize MJ off the ball, and when he did get the rock they would almost always send swarming double teams to force him to give it up. While it didn't always limit Jordan's scoring, the difficulty he had in getting those points and his relative lack of a supporting cast made it extremely difficult for the Bulls to get by their rivals, which they finally did on their fourth try in 1991.

Date: 1989

Prior to his transcendent acting performance in "Space Jam," Jordan tried his hand at playing Oprah in his short-lived local Chicago talk show "Michael Jordan Airwaves." Scant information is available about how this program came to be or why it went off the air, but we're assuming the awkward format and uncomfortable interactions between Jordan and host Jim Rose had a lot to do with it.

Date: 12/10/2008

When you've got a solid leading scorer who is helping you win games, the obvious move is to trade him for pennies on the dollar, right? Well, it is if you're Michael Jordan, who sent Jason Richardson to the Phoenix Suns just 21 games into the 2008-09 season in exchange for the rotund Boris Diaw and a decent bench player in Leandro Barbosa. MJ also threw Jared Dudley into the trade just for fun, and Dudley ended up emerging as an excellent rotation player in Phoenix as well. If the goal of the trade was to suck, it had its desired effect; the Bobcats finished the season 35-47 and failed to make the playoffs yet again.

Date: 1985-1989

Michael Jordan's name is synonymous with all-around excellence on a basketball court, and rightly so. However, there's a dirty little secret about MJ when it comes to scoring, particularly early in his career: he was an atrocious three point shooter. His combined percentage over his first four seasons in the NBA was a staggeringly bad .164, easily the worst in the NBA over that time period for anyone who attempted that many threes (Reggie Theus was the next-lowest at .210; on the other end of the spectrum, Mark Price was the best at .436). While Jordan did turn it around as he got older-peaking with an excellent .427 mark in 1995-96-his lifetime .327 percentage on threes is certainly pretty pedestrian.

Date: 5/26/1997

When you’re up 3-0 in a series, Game 4 is about as low pressure as it gets. For someone like Jordan, though, it also means you have a chance to stomp out your opponent and get some much-needed rest before the next series. Leading 3-0 in the 1997 Eastern Conference Finals, though, MJ went out in Game 4 and unleashed one of the most brutal playoff performances of his career. Not only did he shoot 9-for-35 from the field, but he went 0-for-8 on three point attempts and only managed one assist in 45 minutes of action. While the Bulls lost the game, it didn’t make much of a difference; they came back strong in Game 5, won the series, and would go on to win the title two weeks later.

Date: Training Camp, 1995

Teammates argue all the time, and occasionally it can get physical. Trash talking—especially the vicious brand that Jordan was known for—can often exacerbate these situations. But it’s a little odd that Jordan would choose Steve Kerr as the target for such relentless taunting, and we’re willing to bet he did not think Kerr would fight back. It’s telling that Jordan immediately apologized after Kerr took a swing at him, and that they were all good after that; sometimes the only way to get the bully’s respect is to stand up to him.

Date: 6/8/1997

With his Bulls leading the 1997 NBA Finals 2-1 heading into Game 4, Jordan had the opportunity to put a stranglehold on the series with a strong performance on the road against the Jazz. Instead, he shot a brutal 11-for-27 from the field, scoring a pedestrian 22 points as the Bulls dropped a low-scoring affair to Utah 78-73. It was one of MJ’s worst playoff performances of all-time, which is saying something considering he still managed to lead his team in scoring and had the game tied going into the final quarter.

Date: 9/11/2009

We know, it is MJ’s next-level competitiveness that makes him the greatest of all-time. But sometimes it’s OK to at least pretend to be gracious and not hold grudges. His Hall of Fame induction speech in 2009 was completely devoid of such restraint, and instead MJ used his platform to excoriate the likes of Byron Russell and Jeff Van Gundy, among many others. It was weird and pretty uncomfortable, and while it doesn’t negate what he did as a player by a long shot, it at least make you want to reconsider the sort of hero-worship that typically surrounds any conversation related to MJ.

Date: 5/14/1992

By the time the Bulls met the Knicks in the 1992 Eastern Conference Semifinals, Jordan was starting to gain the "invincible" perception that he still carries with him today. During a pivotal Game 6 in Madison Square Garden, though, he looked anything but. MJ scored just 21 points on 9-for-25 shooting and turned the ball over a stunning seven times as the Bulls fell to the Knicks, forcing a Game 7 back in Chicago. In typical MJ fashion, though, he came out the next game and burned New York for 42 points as the Bulls won the clinching game by 29 points.

Date: 9/11/2002

Say you're the greatest two guard of all-time and are attempting a comeback. You've got a problem: there's another guy who plays the same position, doesn't like you, and is stealing your minutes already on the team. What do you do? Trade him, of course! Jordan's questionable decision-making continued when he decided to swap budding star Richard Hamilton for Jerry Stackhouse, and thus complete an overhaul of his team that would allow Jordan to start 67 of 82 games during the 2002-03 season. Stackhouse played just two seasons in DC (including an injury-plagued 2003-04 where he only participated in 26 games) before being traded to Dallas in the 2004 offseason, while Hamilton would become an All-Star and help Detroit win the 2004 NBA championship.

Date: 2/10/2002

Everyone misses dunks, even the great ones. But to miss a wide open one with nobody even close to you? In front of a global audience watching primarily because of you? Even for someone as absurdly confident as Jordan, that has to sting a little bit. Considering it happened while he was wearing a Wizards uniform, that moment really felt like an imposter had stolen Jordan's identity and had fooled us all. Sadly for us, MJ was just getting old.

Date: 5/24/1993

After conquering the Knicks in seven games the year before, Jordan was probably feeling pretty confident heading into their match-up in the 1993 Eastern Conference Finals. How good was he feeling? Good enough to head on down to Atlantic City the night before the opening two games of the series for some late-night gambling binges. The Bulls ended up losing both contests, falling way behind in the series and creating several must-win scenarios on their home floor. After not playing particularly well in the Game 1 and Game 2 losses, MJ took control of the series and propelled the Bulls to four consecutive wins with several dominant performances, including a 54-point outburst in Game 4 and a triple-double in MSG in Game 5.

Date: 5/7/1995-5/18/1995

Jordan's return in 1995 was supposed to signal the beginning of the next Bulls' dynasty, and a lot was expected of His Airness even though he had not played in over a year. The plan to establish Chicago as a juggernaut would have to wait a year, thanks to the Orlando Magic. Shaq, Penny, and Co. were completely unafraid when they met the Bulls in the Eastern Conference Semifinals, and despite averaging 31.0 points per game in the series Jordan was unable to get his team past their upstart opponents. It would be the last time in his career that he would lose a playoff series.

Date: 10/6/1993

This is a very popular conspiracy theory, one that would explain Jordan's very sudden decision to retire. A year-and-a-half-long suspension for all his gambling issues (and the negative attention they brought on the league), when masked as a retirement, would have had the desired effect for the league without destroying Jordan's marketing credibility. A classic win-win. Unfortunately, we'll probably never know the truth with this one, but all we'll say is it would be shocking if someone as competitive as MJ willingly hung his sneakers up right in the prime of his career after winning three championships in a row.

Date: 2007-Present

The Charlotte Bobcats have been in existence since 2004, with Jordan coming aboard as a minority partner in 2006 and the majority owner in 2010. In the eight years since he got involved with the franchise, the Bobcats have gone through a remarkable seven coaches. Only one (Larry Brown) posted a winning percentage above .400. It does at least look like seven could be their lucky number, as current coach Steve Clifford has the team playing well and in playoff contention. Maybe that will be enough to save his job, at least this season.

Date: 3/12/1997

Even late in his career, Jordan was no slouch on defense; nine All-Defensive First Team awards (including this particular season) prove that. So he probably didn't think much of this undersized rookie guard he was matched up with at the top of the key during this March regular season game, but as the footage shows maybe he should have paid a bit closer attention. Allen Iverson completely broke MJ's ankles, announcing his arrival as a future star in the NBA and vaulting himself to household name-status among NBA fans.

Date: 6/28/2006

While some have claimed otherwise, Jordan's decision to select Adam Morrison at No. 3 overall in the 2006 draft is one of the most disastrous decisions in Bobcats history, and that is really saying something. MJ had just bought his stake in the team two weeks earlier, but that didn't stop him from choosing a guy with little-to-no athleticism over a more logical fit-never mind a better player-like Brandon Roy. Morrison ended up playing all of 130 total games in two and a half seasons with Charlotte before Jordan dumped him to the Lakers, and Morrison's NBA career lasted all of four years total.

Date: 2010

We're guessing Mr. Jordan did not pay much attention during history class. If he did, he might have realized that sporting this style of moustache has gone quite out of fashion these days, given its striking resemblance to the look of one of the most reviled men in history. Come on, Mike!

Date: 1986

Honestly, there isn't a whole lot we can add to this. The ad kind of speaks for itself. We will just say that both MJ and the female reporter have no regard for the boundaries of a typical journalist-athlete relationship, which is deeply troubling indeed. Also, why is a bald man promoting women's hair care products?

Date: 2/7/1994

Everyone knows about Michael's foray into baseball, and his relatively hasty return to basketball. His AA stats with the Birmingham Barons make it pretty clear as to why he didn't last: a .202 batting average isn't enough to get anyone to the Majors, nor is a whopping 114 strikeouts in 436 at-bats. While it's kind of amazing that MJ was a good enough athlete to play on any level of pro ball, he was clearly overmatched and over his head on the diamond.

Date: 1985-Present

It makes positively no sense that someone with so much money and so much fame could be such a horrible dresser. This has been a career-long affliction for Jordan, who was an equally bad dresser early, in the middle, and late in his playing career. His ownership days have done little to change his poor choices, but at least now he has the excuse of “I own an NBA team and I’m Michael Jordan. I can wear whatever I want.”

Date: 6/27/2001

We all know the NBA Draft is a total crapshoot, but this was a pretty epic miss. Jordan's decision to select Kwame Brown No. 1 overall instead over Tyson Chandler or Pau Gasol quickly proved to be a disastrous mistake, one that still holds as the signature move of his entire front office career. Kwame was actually still somehow hanging on in the NBA this season until he was cut by the 76ers in November, but with career averages of 6.6 points and 5.5 rebounds per game it isn't looking like he'll find new employment any time soon.