Michael Jordan's competitive nature is the stuff of legend — responsible not only for unprecedented success in the NBA, but also a post-basketball life that has made him one of the "most powerful NBA owners" and the figurehead behind the popular Jumpman imprint which continues to carry Nike to new heights.

While to err is simply human, Michael Jordan has used that tireless desire for winning to avoid any major missteps aside from that fateful year of minor league baseball after he became disenfranchised with basketball following the death of his father.

But even the biggest MJ "Stans" might be surprised to learn that Jordan's foray into baseball isn't his only misstep in the athletic realm. There was a time right after his last retirement when he bet on himself as the owner of a superbike motorcycle team, aptly titled "Michael Jordan Motorsports."

Combining elements relating to high-octane performance and merchandise, Michael Jordan Motorsports could and probably should have been an added dimension to his portfolio of assets. But the venture never took hold; immortalized by a friends and family Jordan IV "Motorsport" silhouette which was given out to team members in 2006 and recently retroed — a not-so-subtle reminder of His Airness's need for speed.

Michael Jordan Motorsports wasn't as unlikely a venture as it may seem given the automobile ties to some of the Jordan Brand's most popular silhouettes over the years — highlighted by the Air Jordan VI being based of the Porsche 911, Air Jordan XIV based off the Ferrari F335 and 550M, Air Jordan XVII based off the Aston Martin, Air Jordan XXI based off the Bentley Continental GT Coupe, and elements of the Air Jordan 31 based on Ferrari seats.

When the Chicago Bulls drafted Jordan with the third pick in the NBA draft, one of the major stipulations was that he could no longer ride a motorcycle for fear that even the most minor an accident could jeopardize a team's fortune - highlighted by that very thing which occurred to the Bulls 20 years later when their top pick, Jay Williams, crashed his motorcycle and nearly died.

"I started riding dirt bikes when I was 7 or 8 years old," Jordan recalled. "Way back when. I kind of got into it, and obviously I couldn't ride because of my contract stuff. But as soon as that was over with, I got back into it."

"It's skillful. I grew up in NASCAR, so I've been a big race fan," Jordan added. "But the thing about motorcycles is the instinct, the reactions — you see the riders working the bike. It takes a lot of skill to be in position on the bike, to be able to downshift and upshift and all that stuff, which is a little bit different than NASCAR. NASCAR is always left-hand turns, and circles the whole time. There's an art to what they do, I'm not diminishing that. I just felt from coming from a sport where it's a reaction sport, to see how they react much quicker — their decision-making has to be really quick. I was intrigued by that."

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According to Kenneth Abbott, Jordan's media manager, Jordan decided to explore his motorsport options after a chance encounter with James Casmay — a Chicago-based motorcycle enthusiast — who often zipped around the city and enjoyed talking intricacies of motors and tires with fellow riders.

"One of the guys went up and started talking to Mike and said, ‘If you want to go riding, here’s my card, give us a call,'" Casmay recalled of his first interaction with Jordan at a Chicago gas station.

"We started having a good time riding late at night, probably ride at 1 o'clock, 1:30, up and down the freeway," remembered Jordan. "Once I started coming out, everybody seemed to migrate to where I was riding. Instead of riding with eight or nine guys, we started riding with 30 or 40 guys, which is just an accident waiting to happen. So we started trying to secretly get out. But obviously once they saw I was out, everybody started looking for me."

Despite Jordan's seemingly endless amount of wealth and access to some of the brightest apparel minds in the business, Casmay and other riders were struck by just how ill-equipped Jordan seemed to be for riding a high-performance motorcycle on the Chicago streets.

"I'm looking and I'm like, 'something's not right with this picture,'" recalled another rider, Noble Williams, a Chicago police officer who noted that Jordan's attire was more akin to how a person would warm up for a basketball game than go for a motorcycle ride. "The whole thing was just wrong. He came up with a Jordan shirt, jogging pants and Air Jordan shoes."

"The gloves he had on were the weightlifting gloves that had the fingers cut off the front," recalled another rider, Montez Stewart, who would prove to be instrumental in Jordan's first major venture after he had retired from the NBA. "It was funny. When I saw that, I was cracking up."

Much like a rookie accepting ribbing from veteran players, Jordan was appreciative of the riders' concern.

"If it wasn't for those guys, I could have gotten myself injured, and would have never been in this sport," recalled Jordan.

Jordan eventually made good and phoned Casmay to discuss if there were any opportunities to take a local rider and give him a push toward a professional career. Casmay insisted that Montez Stewart was that guy.

“We had no intentions of starting a race team,” said Casmay, who was running a small investment company at the time. “But after introducing Montez to Mike, we said, 'you know, this is fun on the streets, but it’s more fun on the track.'”

After a day at the track where Jordan assessed Stewart's racing acumen, he knew he was the perfect rider to serve as the inaugural pilot for the yet-to-be-minted motorsports team.

Ken Abbot, CCS-Formula USA Road Race Competition Director, said of Stewart's abilities at the time that he was “probably the dominant rider in the Midwestern Region of the CCS by the end of the 2003 season.”

"He asked me as friends, 'Montez what can I do to help you fulfill your dream as a road racer?" Stewart recalled. 'If you're serious, we can pursue this together.'"

Although it took Jordan 20 years to rekindle his passion for motorcycles, he established Michael Jordan Motorsports in 2004 with the help of Pete Mauhar — a seasoned team manager in the pro circuit with a decade worth of Superbike experience — to help him navigate a sport dominated by factory teams from Suzuki, Honda, Kawasaki, Ducati and Yamaha since the sport was officially recognized on a global scale in 1988.

“I got a call from James Casmay, someone I didn’t know, who was asking about whether we’d want to help Michael Jordan go into racing. Which was a pretty bizarre call, really,” Mauhar said. “Honestly, I thought it was some of my friends messing around with me.”

While it takes a motorsports team a year or longer to secure sponsorship, get equipment, find riders and mechanics, and get approval from the sanctioning body for SBK, Jordan Motorsports managed the monstrous task in only five weeks time — surely aided by Jordan's name recognition that had people on the periphery of the sport buzzing.

According to Forbes, "Almost overnight, Yamaha had provided new bikes fresh off the boat from Japan at a discounted price. Then those bikes were sent to Gemini Technology Systems, a Wisconsin company that makes motorcycles race-ready and provides crew and race team management. Gemini even applied the Carolina Blue color scheme to honor Jordan’s old college team."

With sponsors like Jordan Brand, Gatorade, Hanes, Upper Deck, and the National Guard painted on the side of his YZF-R1 AMA Superbike, Montez Stewart was on the starting grid at Daytona for the first American Motorcyclist Association (AMA) road racing event of the 2004 season.

“I’ve done a lot of club racing, and I always wanted to be a pro racer and come race with the AMA and run with the big boys,” Stewart said at the time. “So I’m really glad to be here.”

As The Los Angeles Times noted in its coverage, "Michael Jordan attracted most of the attention before the main event as the retired NBA legend was on hand to encourage his young protege, Montez Stewart of Matteson, Ill. It didn't help much, however, as the rookie rider — who looks more like an NBA prospect at 6' 3" than a motorcycle racer — qualified 33rd in superstock and 39th in supersport."

Stewart turned lap times good enough to make the grid in both classes. In Superstock, Stewart qualified in the ninth row, turning laps at 1:58.620. In Supersport qualifying, he made the grid in 43rd position, turning a fast lap of 2:01.075.

Stewart ultimately finished 26th at Daytona and 23rd overall in the standings out of 40 riders for the entire season.

For some, this may have been a small victory. But for Michael Jordan, how would he interpret a middle-of-the-pack finish?

"Knowing me, I wanted to win the first year," Jordan told E60. "But I knew — mechanically — I didn't have the right equipment to win. But that doesn't mean that I don't hope for some type of win," while adding, "I  like being the underdog. When you least expect it, you go out and find ways to beat the favorites. It's tough, because the factory teams are well-equipped. But what's starting to happen is they're seeing no matter what, my interest and my passion is strong enough that, sooner or later, I'm going to find the right things that make it work, and get us up in front and get us winning."

Whereas branding and motorsports often meld machine and merchandise, Jordan's involvement also allowed his team to bring footwear into the mix thanks to the help of Nike designer Mark Smith, who helped design the look of the bikes so that they could be paired both with the latest Jordan game shoe and retros.

“We weren’t doing it to create any heat in the market with sneakerheads,” Smith said. “What I was doing was making something specific for the race team. And it’s appropriate, it matches up with the bike and it matches up in the paddock. I look at things as a photograph. There was nothing better than a pair of sneakers on a motorcycle. That was enough of a reason to do it.”

A prime example of this fusion came in 2009 when Smith designed the 6 Rings sneaker, which matched nicely with a bike heavily draped in a classic elephant print.

Despite the "look good, perform good" mantra, Jordan Motorsports failed to win a single race after 93 appearances at various events between their inaugural season and 2010.

If Michael Jordan's various championship-winning Bulls are viewed as the benchmark for NBA success, then Suzuki's Yoshimura factory team during this period could best be described as a dynasty — winning 10 consecutive championships and 53 straight races — and owning the new millennium between 2000-2010.

"I felt like it was an unfair playing ground," Jordan said. "When manufacturers were winning every single race. We didn't have the parts. Obviously we didn't have the technology. We had no chance at winning."

2009 ultimately marked a radical shift in the rules of superbike racing — creating uniformity amongst suspension, tires and engines that teams were able to use.

"I am a competitor to the end, and I will fight until I get to the front," Jordan said a year later, adding "may the best rider win."

Jordan's team went from a single top-three finish in 2008 to ninth the following year. However, he still hadn't managed to crack the winner's circle despite the hit that Suzuki had taken following the rule changes.

The Jordan Motorsports drought ended in 2010 when Jake Zemke took the basketball legend’s race team to Victory Lane at Daytona International Speedway while Jordan watched from the press box. It was clear that Jordan wanted to go down and celebrate, but instead he opted to let his rider and crew relish in the achievement.

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In subsequent seasons, Jordan Motorsports added Ben Bostrom and his Suzuki GSX-R1000 bike to the team — draping the machine in a Chicago Bulls colorway and signature ’23’ logo on the front and rear end.

Bostrom would finish in second place during a rain-soaked race at Barber Motorsports Park in 2011.

“A huge thanks to the Jordan Motorsports boys,” commented Bostrom. “The results were not what I hoped, but the bike has really come together and now the rider has to step it up. We’ve struggled for a few events for sure and it’s nice to have fun riding again. We’ve got a few weeks off to ready ourselves for Mid-Ohio, where I’m sure the Jordan bike should be at the front. The bike is ready, the rider needs a little work and we will have a winner. I like Mid-Ohio and so do the Suzukis, so let’s see if we can sweep another podium in three weeks.”

In 2013, Michael Jordan Motorsports announced that it was suspending operations of its AMA Pro Superbike team and would instead focus on transitioning to international competition as early as 2014.

“We’ve decided to not move forward with our AMA Superbike program,” Michael Jordan Motorsports Corporate Relations Director Kreig Robinson said. "We have no bad feelings toward AMA Pro Racing. This is where we are, where we’re from. We like the property. We don’t have any bad feelings toward anyone in particular, but the property as it stands right now doesn’t allow us to go out and get the sponsorship that we need."

Even with Michael Jordan's involvement and a financial commitment of $1 million annually (of a $5 million operating cost), the loss of key sponsors like the National Guard ultimately proved to be the final nail in the coffin.

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