Ranking the 10 biggest stains on Michael Jordans' legacy

03/20/2025 01:20 PM

Michael Jordan is seen by many as the greatest NBA player of all time. But while his talent and accomplishments are nearly untouchable, there’s no doubt that it wasn’t a perfect legacy for His Airness. Here are the 10 biggest stains on Michael Jordans’ legacy, ranked.

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1. Michael Jordan’s gambling addiction

One of the biggest concerns that marred Jordan’s career was his gambling addiction. In fact, his habits were even well-documented in the public eye. There were plenty of stories and conspiracy theories that surrounded His Airness, especially when he announced his first retirement in 1993 in relation to his father’s death.

James Jordan, the father of Michael, was found dead as it was initially suspected to have a connection with his son’s gambling habits. While his gambling never exactly spilled over his performances on the court, his addiction to it doesn’t make him the best role model.

2. Michael Jordan’s response to Nike’s unfair labor practices

Jordan and Nike carved out one of the biggest success stories in relation to sports and business. But while the partnership led to some of the most iconic sneakers, it wasn’t exactly a picture-perfect relationship. In fact in 1996, Nike was ordered to improve its working conditions, as human rights and labor advocates attacked the sports sneaker and apparel giant.

Wanting to get a response from their top endorser, at the middle of the 1996 NBA Finals, Jordan made a controversial response that only revealed his intention of keeping his impact within the sport and not beyond the realm of social justice.

3. Michael Jordan’s three first-round playoff exits

Before Jordan started winning championships, he ultimately struggled in the playoffs. In fact, his first three postseason appearances resulted in three-consecutive first-round exits. As a result, Jordan’s playoff record at that point was 1-9. Afterwards, he would suffer three more eliminations before finally kicking off his first three-peat with the Bulls.

4. Michael Jordan was a poor three-point shooter

Although Jordan dazzled basketball fans around the world with his crazy acrobatics in the air, there’s a huge knock against his game, which was his three-point shooting. Shooting is one of the major aspects in basketball, and given that this is the weakest arsenal in the GOAT’s play style certainly triggers some doubters. Throughout his career, Jordan only shot 32.7% from downtown. He even shot as low as 13.2% from beyond the arc during the 1987-88 season.

5. Larry Bird’s Boston Celtics were Michael Jordan’s kryptonite

Another huge knock in Jordan’s legacy was his inability to defeat Larry Bird’s Boston Celtics in the playoffs. At the 1986 NBA Playoffs in the first round, Jordan’s Bulls were swept by Bird’s Celtics. The series saw Jordan’s NBA playoff record of 63 points go for naught. A season later, the Celtics reasserted their mastery over the Bulls by sweeping them again in three games.

6. Questioned validity of Michael Jordan’s DPOY Award win

Winning the NBA Defensive Player of the Year Award initially improved Jordan’s status as the GOAT. But while His Airness was regarded as a defensive menace during the 1987-88 season, recent reports have claimed that his production on the defensive end raised some doubts.

In fact, the latest research suggested that among the award winners, Jordan registered the biggest differential in home vs. away statistics. Of course, doubts continued to be fueled when former NBA stat keeper Alex Rucker confessed to inflating statistics.

7. Michael Jordan’s ownership stint with the Charlotte Hornets

While Jordan was one of the best players in the sport, being a basketball executive shows otherwise. His Airness bought the franchise back in 2010. As the owner of the Charlotte Hornets franchise, formerly called the Charlotte Bobcats, the team only made the playoffs twice, all of which resulted in first-round exits. During that stretch, Charlotte also only posted a 423-600 overall record under Jordan’s term.

8. Michael Jordan drafting Kwame Brown with the first-overall pick

Before becoming the owner of the Charlotte Hornets, Jordan already had his feet wet as an executive for the Washington Wizards before coming out of retirement to play for the team. In his executive tenure, Jordan made a questionable move during the 2001 NBA Draft by selecting Kwame Brown with the first-overall pick. Brown became one of the biggest busts in NBA history.

9. Michael Jordan had most misses in a playoff game

Jordan has set a lot of records during his playing days. However, not all of them actually help his legacy. In fact, he set one of the most embarrassing records at the 1997 Eastern Conference Finals against the Miami Heat. In Game 4, Jordan scored 29 points but only shot 9-of-35 from the field overall. His 26 misses continues to be the most by any player to this day. The record would later on be matched by Kevin Durant in the 2016 NBA Playoffs.

10. Michael Jordan ending his playing career with the Wizards

Although it’s not totally a knock on his career, however, basketball fans probably would have preferred Jordan to end his career with the Chicago Bulls. It would’ve been a fitting end for the GOAT. But to everyone’s surprise, Jordan chose to come out of retirement to play for a bottom-feeding Washington Wizards squad. Jordan never made the postseason as a Wizard. Moreover, it also fueled his critics for failing to prove that he could win a chip without the help of Scottie Pippen and Phil Jackson.

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