Twenty-six.
That is the number of times Michael Jordan was trusted to take the game-winning shot and missed. It’s a specific, stinging statistic that Jordan himself laid bare in one of the most famous commercials in television history. We see the highlights—the six rings, the shrug, the Flu Game, the gravity-defying leaps—but we rarely sit with the fact that the most dominant athlete of the 20th century built his entire brand on the back of his own shortcomings. Michael Jordan on failure isn't just some marketing gimmick; it's a blueprint for how a human being survives the meat grinder of professional sports and comes out the other side as a billionaire icon.
Most people look at MJ and see a god. They see perfection. But if you actually listen to what the man says, he describes himself more like a relentless scavenger of lessons found in the dirt of defeat.
He didn't just "overcome" failure. He used it as high-octane fuel.
The Laney High School Myth and the Reality of Rejection
You've probably heard the story. Michael Jordan, the greatest basketball player ever, was cut from his high school varsity team. It’s the ultimate underdog trope.
Except, he wasn't really "cut."
In 1978, at Laney High School, Jordan was a 5'10" sophomore. The varsity coach, Clifton Herring, needed size. He passed over Jordan for his friend Leroy Smith, who happened to be 6'7". Jordan was assigned to the junior varsity team. To a teenager with an ego the size of North Carolina, that felt like the end of the world. He went home, locked himself in his room, and cried.
But here is where the Michael Jordan on failure philosophy actually begins. He didn't quit. He didn't transfer schools. Instead, he used Leroy Smith’s name as a mental trigger for the rest of his life. Every time he didn't want to practice, he thought of the guy who took "his" spot.
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This is the nuance we miss. Failure wasn't a stop sign for Jordan; it was a calibration tool. He played JV, dominated, grew four inches, and by the time he hit varsity, he wasn't just good—he was possessed. That obsession with being passed over created a chip on his shoulder that stayed there through his final days with the Wizards.
Missing the Mark: The Math of the 9,000 Misses
"I've missed more than 9,000 shots in my career."
Think about that number for a second. That is more shots than most NBA players even attempt in a decade. To miss 9,000 times, you have to be willing to take 9,000 shots where you might look like an idiot. You have to be okay with the "clank" of the rim echoing in a silent arena.
Jordan’s relationship with Michael Jordan on failure is essentially a lesson in high-volume risk-taking. Most people are so afraid of the 26 missed game-winners that they never take the first one. They’d rather be 0-for-0 than 26-for-52. Jordan realized early on that the math of greatness requires a massive graveyard of attempts.
He lost almost 300 games. He failed over and over and over again. And that, as he says, is why he succeeded. It’s a paradox. You can't have the "Last Dance" without the years of getting bullied by the "Bad Boy" Detroit Pistons in the late 80s.
The Detroit Pistons and the "Jordan Rules"
Before the championships, there was the pain. From 1988 to 1990, the Detroit Pistons were Jordan’s personal nightmare. They didn't just beat the Bulls; they physically assaulted them. Chuck Daly’s "Jordan Rules" were simple: if Michael goes to the air, put him on the ground.
He failed to get past them three years in a row.
A lot of superstars would have demanded a trade. They would have complained that the league was too soft or that their teammates weren't good enough. Jordan did something different. He went into the weight room. He added fifteen pounds of muscle so he could take the hits. He stopped trying to beat Detroit alone and started trusting Phil Jackson’s Triangle Offense.
This shift is crucial for anyone studying Michael Jordan on failure. Sometimes, failure isn't about working harder; it's about pivoting. It’s about realizing that your current method has reached its ceiling. Jordan’s ego was his greatest strength, but his ability to subordinate that ego to a system—after failing repeatedly—is what actually won the rings.
The Baseball Interlude: A Public Failure
When Michael Jordan retired in 1993 to play minor league baseball for the Birmingham Barons, the media had a field day. They called it a midlife crisis. They called it an embarrassment. Sports Illustrated famously ran a cover with the headline "Bag It, Michael," essentially telling the greatest athlete on earth to stop embarrassing himself.
He was hitting .202. In the world of professional sports, that’s failing.
But if you ask the people who were there, like his manager Terry Francona, they’ll tell you Jordan was the first one at the park and the last to leave. He was a 31-year-old multi-millionaire riding on a bus in the Southern League, getting paid $850 a month, and struggling to hit a curveball.
He failed at baseball. But he didn't fail at the process.
The baseball stint is often looked at as a weird footnote, but it was actually a mental reset. It allowed him to be a "rookie" again. It stripped away the invincibility. When he returned to the NBA in 1995, he wasn't just the same MJ; he was a smarter, more calculated version. He had failed on a global stage and realized he was still standing. That lack of fear is a superpower.
Why the "Mamba Mentality" Owes Everything to MJ
We talk about Kobe Bryant’s legendary work ethic, but Kobe was the first to admit he modeled his entire psyche on Jordan. The core of that mindset is the refusal to let a mistake dictate the next move.
If Jordan missed a shot, he didn't think, I’m having a bad night. He thought, The next one is going in because I’ve done the work. There’s a psychological concept called "self-efficacy," which is basically your belief in your ability to succeed in specific situations. Jordan’s self-efficacy was bulletproof because he viewed failure as data. Missed a jumper? Your elbow was too far out. Lost the game? Your defensive rotation was slow. It was never about "not being good enough." It was always about a technical error that could be fixed.
The Business of Failure: Brand Jordan
Jordan’s sneakers are a multibillion-dollar empire. But even in business, the Michael Jordan on failure mantra applies. Not every shoe was a hit. Not every business move was perfect (looking at you, Charlotte Hornets ownership).
His tenure as an executive and owner is often criticized. He drafted Kwame Brown with the number one pick—a move widely considered one of the biggest "fails" in NBA history.
Does it tarnish the legacy? Only if you think a legacy has to be a straight line. Jordan’s willingness to be wrong, to draft the wrong guy, or to make a bad trade is the same willingness that let him take the shot in 1998 against Utah. You cannot have the highs of the Jordan Brand without the risks that occasionally lead to the lows of the Hornets' win-loss record.
Actionable Lessons from the GOAT’s Grittiest Moments
If you want to apply the Michael Jordan on failure mindset to your own life—whether you're an entrepreneur, an artist, or an athlete—you have to stop treating "losing" like a tattoo. It's not permanent. It's a bruise.
1. Increase Your "Shot" Volume
You aren't failing because you aren't talented; you're failing because your sample size is too small. Jordan missed 9,000 shots because he was brave enough to take way more than that. If you want to succeed, double your failure rate. Send more emails. Write more pitches. Start more projects.
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2. De-personalize the Loss
When Jordan lost to the Pistons, he didn't decide he was a "loser." He decided his body wasn't strong enough. He turned a vague emotional pain into a specific physical problem. When you fail, don't say "I'm bad at this." Ask, "What specific skill did I lack in this moment?" Then go get that skill.
3. Use the "Leroy Smith" Factor
Find your "chip." It doesn't have to be healthy, honestly. It just has to be effective. Jordan used every slight—real or imagined—to keep himself from becoming complacent. Use your doubters as a battery.
4. Embrace the "Minor League" Phases
Don't be afraid to be a beginner at something, even if you're an expert at something else. Jordan’s time in baseball was a masterclass in humility. Being willing to look "bad" while you learn a new craft is the only way to eventually look "great."
5. Focus on the Next Play
In the 1998 Finals, Jordan missed a shot, got back on defense, stole the ball from Karl Malone, and then hit the game-winner. He didn't mope about the miss. He didn't celebrate the steal. He just moved to the next requirement of the moment.
Failure is only a "conclusion" if you stop moving. For Michael Jordan, it was always just a transition. He proved that the person who can fail the most, and keep going, usually ends up with the trophy.
The secret isn't that he never failed. It's that he was never afraid of the 27th missed game-winner. He was only afraid of not being the one to take it.
To implement this today, identify one area where you've been "playing it safe" to avoid embarrassment. Commit to taking ten "shots" in that area this week, with the explicit goal of learning from the misses rather than mourning them. Real growth happens in the recovery from the clank, not just the celebration of the swish.