In late 2009, Ken Eller was hanging out with a friend at home when they watched a documentary called My Date With Drew. In the movie, Brian Herzlinger, a regular guy, documents his quest to go on a date with his celebrity crush, Drew Barrymore, which — spoiler alert — he succeeds in doing by the end of the film.

After the movie ended, Eller turned to his buddy and told him he would change the premise of the film. He would instead set a goal to play Michael Jordan in a game of one-on-one. Eller had been a huge Jordan fan growing up, but he hadn’t played basketball or even really stayed in shape for more than a decade. It all sounded far-fetched. Still, Eller was set on giving it a shot.

When I first read about Eller’s story, it seemed ridiculous. He had emailed me to let me know he had checked out my blog, where I had done a series of posts on Jordan. I clicked on his website, which was in his email signature. When I started reading his story, it seemed like that of just another person with a crazy idea that was going nowhere. It even felt like it could be an intrusion into Jordan’s privacy. “It’s always a fine line to walk. I’ll go around, put a lot of work in, and travel all over,” Eller later explained. “But I don’t want Jordan to think I’m stalking him, nor do I want him to feel uncomfortable. I think he gets a kick out of it. I really do.”

The more I talked to Eller, the more my skepticism faded. I began to realize how far he’d come in his quest to play Jordan. There was a huge financial commitment involved to give himself even a shot to make it happen. Not everybody can spend thousands of dollars and untold hours chasing a pipe dream. But still, it was impossible to ignore all the good that had come out of Eller’s journey. He was motivated by a single purpose, and then found out there were so many other goals he cared about.

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Nine months after he came up with his goal of playing Jordan, Eller started mevsMJ.com. He was now in his early thirties, married, and working full time in financial services.

Eller thought this would be simple. He would get in shape, then incorporate basketball training into his life, and it would all culminate with a one-on-one game against Jordan. He expected it to take about a year, and was excited to document it on his website. Eller had no kids, so he had extra time to prepare.

By 2010, Eller was participating in half-marathons and working out regularly at Orlando Hoops, a basketball training facility in Florida. Now that his adventure was under way, Eller needed to address the most important part of his goal: finding Mike.

Eller already knew how he would make it happen. He had been saving up money to attend the Michael Jordan Senior Flight School, an annual three-day event that Jordan organized. Registration, which cost $15,000, was limited to 60 to 70 people. For that price, attendees got to be on the same court as Jordan. The Bulls legend often brought in former players, speakers, and coaches. Guests had included Charles Barkley, John Thompson, Mike Fratello, Gene Keady, and Mike Krzyzewski. Camp attendees received Jordan apparel, ran basketball drills, and, because the camp was often held in Las Vegas, there were extracurricular activities such as poker tournaments.

“It’s the most expensive camp, but it’s with Michael Jordan,” he told me. “I’ve got passion and a vision for what I want, but I knew I had to be smart about approaching my goal. Working in finance, I realized that spending $15,000 on a basketball camp wasn’t the best use of my funds. But I was prepared to go ahead with it.”

Eller heard stories about how Jordan would hand-pick selected attendees and play them one-on-one. He hoped that by starting his website almost a year before the camp, it would help create a buzz about what he was trying to do. Eller was counting on Jordan’s notoriously competitive nature.

But a few months before the camp was scheduled to be held, Eller found out it had been canceled. Jordan had decided to focus on his charity golf tournament instead.

At the end of 2011, Eller found out that Jordan would be attending a college basketball game at the University of Central Florida, where his son Marcus was playing. So he went to the game and managed to pass along his business card to Jordan. On the front of the card was an iconic photo of Jordan dunking. On the back was information about Eller’s goal to play him one-on-one.

The next day, Eller checked his website’s analytics and found that someone from Illinois had spent an hour and 41 minutes on his site. This person visited 116 different pages — pretty much every blog post. There was no way to prove this was Jordan. But Eller saw this as a positive sign. Even if it wasn’t him, he thought, maybe it was someone connected to him.

A year later, Eller attended the Charlotte Bobcats fantasy camp. Wearing a mevsMJ.com shirt, he approached Jordan in the gym and asked if he’d had a chance to visit his website. Jordan said no, but agreed to check it out afterward. Almost three years in, Eller had finally come face-to-face with his white whale, but he was still no closer to getting a commitment from him to play one-on-one.

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We all have our own reasons for admiring the best athletes in the world, but none of us have ever devoted years of our lives trying to get them to play us one-on-one.

“One, he’s a winner. I also think it’s his determination and work ethic. I’ve always been intrigued by people who are excellent at what they do. I want to understand what makes that person better. A lot of people can jump, dunk, and shoot, but very few of them put it all together,” Eller said. “That was the intriguing part for me. He had everything. He had a storybook career.”

Even though he wasn’t making much progress with Jordan, other things started to happen. Eller reached out regularly to college players and other pros to see if they were interested in playing him one-on-one.

In January 2013, Corey Maggette — who was with the Detroit Pistons at the time — liked one of Eller’s Instagram photos. When Eller said thanks on Twitter, Maggette retweeted the message.

Just got an instagram like from the NBA's @ghostC5M (Corey Maggette) – Your support means a lot! (http://t.co/tnpsA6fK http://t.co/9HOTyT08 — Kenny Eller (@KennyEller) January 17, 2013

Eller had met Knicks assistant coach Dave Hopla during his basketball training, and told him about his Maggette encounter. A few days later, the Knicks and Pistons happened to be playing in London. Hopla spoke to Maggette there, and told him Eller’s story. A week later, when the Pistons were in Orlando to play the Magic, Eller bought two tickets to the game.

Along with his wife, he sat by the tunnel where the players came out of the locker rooms and onto the court. Eller had been messaging Maggette on Twitter leading up to the game, asking for his shirt size so he could give Maggette a mevsMJ.com shirt. When Maggette came out of the locker room before the game, he acknowledged Eller. The two agreed to meet. After the game, Eller told Maggette all about his curious quest. Bo Outlaw and Joe Dumars happened to be standing nearby. Intrigued by Eller’s shirt, Dumars — a rival of Jordan’s during his playing days — asked about his website. Eller said Dumars was fascinated, and told him to keep going and see it through.

Since then, Eller has played street ballers, college players, and even DeShawn Stevenson (who beat our hero, 3 games to 0, in a best-of-five one-on-one matchup).

Nick Anderson has trained with him, Toni Kukoc has sent him a message of encouragement, and he’s met with Chandler Parsons at a basketball camp.

Eller also used his Jordan quest to become more involved in the Orlando community. One of the first players he played, when he began training, was Robert Brown, a high school prospect who went on to play at Virginia Tech. Eller knew Brown’s father (the two played basketball together a decade ago). Through this connection, he also met Robert’s younger twin brothers, Anthony and Avery, who are playing basketball at Lake Minneola High School.

Eller regularly visits the school, plays basketball with the kids, and gives speeches to students ranging from kindergarten to fifth grade. He encourages them to believe in faith and hard work, using his story as an example.

Last year, Eller flew Carlyle Holder — a teammate of the Brown twins — to Charlotte to attend a basketball camp. He brings Anthony and Avery to basketball camps in Orlando when he can to give them new experiences and help them build confidence in front of large groups.

“When I was 15 years old, I used to coach a youth basketball team. I seriously considered becoming a counselor before choosing my finance career,” Eller said. “When you can encourage these kids … to see their demeanor, body language, and confidence change over time, it’s phenomenal and very rewarding.”

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I asked Eller whether he thinks this journey has changed him. “I’m the same person, although it has changed my perspective on certain things. At the start, I was greeted with so much negativity and people saying it would never happen. People would just laugh at me. It’s definitely changed the way I think, when people ask me for things. I remember being at a basketball camp and the kids asked me to play at the end of a long day. I was hungry and didn’t want to. Before, I probably would have found a way to not do it. But now, the first thing that pops into my head is that people always say no, when it’s sometimes so easy to say yes.”

While Eller still hasn’t achieved his end goal more than five years later, the pursuit turned into something more along the way.

“I think it’s changed my overall focus in life. For a while, being in finance, I was very money-motivated. Now all I want to do is help people.”

In April this year, Eller attended the Michael Jordan Celebrity Invitational Gala in Las Vegas. At the event, he bumped into Jordan’s two sons, Marcus and Jeff. To his surprise, Jeff was familiar with his website. The two exchanged numbers and promised to keep in touch. During the party, Marcus approached Eller and asked if he wanted to be formally introduced to his dad. Eller was elated. The two of them shook hands and spoke for a few minutes, and ended up taking a picture together.

Jordan playfully told Eller that he would play him anytime. But there are still no plans for a one-on-one game.

Eller’s wife, Charissa, has been supportive from day one, and continues to believe in her husband’s quest. “I think the word ‘realistic’ is relative,” she explained. “I feel that if you want something and you are persistent and focused, anything can become reality. When he told me about his goal of playing Jordan, I immediately envisioned it happening. Ken doesn’t allow anyone to take away his positive approach.”

A person with another motive or, let’s be honest, less money, might have given up by now. Or they might have been more focused on selling T-shirts or leveraging the connections he’s made in the league for some sort of celebrity status.

Eller said he doesn’t care about any of that stuff. He’s not even a great basketball player. It’s not a matter of pride or ego, to see if he can beat Jordan now that he’s past 50. “Honestly, I don’t know that I would score against him. I’m wild enough to have this dream of playing him, but I’m not crazy. Even at his age, I still realize he was the greatest basketball player ever. I’m 37 now. I’m definitely not the greatest basketball player ever.”

I asked Eller what his strategy would be, were he ever to actually play Jordan. “I can’t let you write about that,” he joked back. “You know what, I would take anything he’d give me. I’m a shooter, so I would try to react to what he would give me, and just do my best.”

As we talked, the conversation turned to how his quest has changed his life. For Eller, it’s been worth it, even if he never plays Jordan. “There’s no regret at all. Sometimes you just have to put yourself out there and take risks.”

But what if he never plays Jordan?

Eller stopped me.

“It’s going to happen. Absolutely. I mean, it’s just a matter of when and where. It’s going to happen. There’s no doubt about it. I don’t hope. I truly believe.”

Alex Wong (@steven_lebron) is a freelance writer from Toronto who lives in New York City.