When appraising the Webby Awards over the entirety of their 29-year history of passing out silver statues to the best content originating on the web, it’s challenging to account for the circumstances behind every upset victory, or to spotlight the creators of every project that surmounted overwhelming odds to bring home the slinky-shaped statues of silver binary code.
The preponderance of evidence suggests that one of the top contenders for that honor has to be winner of the Video & Film Sports 2025 category, a project that was both inspired and created by one of the most compelling collections of underdogs to ever receive an official nomination from the Webby Awards, let alone a victory.
Seated in Cipriani Wall Street on a night when Snoop Dogg, Taylor Swift, and Caitlin Clark were honored was a 6’8” figure whose status as the most unassuming figure to ever have their own signature basketball shoe will probably never be withdrawn.
It’s difficult to fathom that a person could have a name that’s more recognizable than their face, and a story more identifiable than their name. Yet, that’s the situation that Leroy Smith has been immersed in for four decades, at least to those who know basketball lore. Even among those who think they know Smith’s face, the visage that’s been popularly paired with his name was disparaging by design, in a clear attempt to create a villain worthy of the heroic figure he’s said to have had a hand in spawning, innocently and unintentionally.
Smith’s cameo appearance at Michael Jordan’s 2009 Basketball Hall of Fame induction ceremony saw him cast as just another figure that the greatest basketball player of all time trotted out in the cavalcade of antagonists that had been overcome along the way. Smith’s offense? He was deemed a more worthy candidate than Michael for placement on the Laney High School varsity basketball team, an honor usually reserved for juniors and seniors anyway.
During the remaining years the two spent as teammates at Laney High School, Michael’s improvement was exponential. When the two reunited after their respective freshman seasons in college—Jordan at the University of North Carolina in Chapel Hill and Smith at UNC-Charlotte—it became clear to Smith that the separation in talents between the two of them, once microscopically in his favor, had swung demonstrably in the other direction.
“It was obvious that Michael was a different player. His game had elevated. He was doing things that I hadn’t seen in college, and certainly not in high school when we used to play against each other,” stated Smith. “At that point, I said ‘We are never going to play each other again!’ You could see that his development had skyrocketed, and I had areas for massive improvement. I was bigger, so I could do a jump hook, but he was quicker, faster, more explosive, and he could get to the rim whenever he wanted.”
It wasn’t Smith’s fault that Jordan was left off the Laney basketball team in his favor, nor could Leroy help it that Michael went on to become the greatest basketball player of all time. Yet, by proxy, that altogether incidental relationship from Smith’s childhood became the most important detail of his life, at least as far as the majority of other people were concerned.
“For years, I just marinated in being the guy connected to Jordan,” added Smith. “I used to hear people talk about the story of Jordan getting cut from the varsity team, and they didn’t realize the guy who got the spot instead of Jordan was standing right in front of them.”
The tale of Smith being the player who was blamed for keeping Jordan from making the Laney High School varsity team—thereby prompting Jordan to develop the determination, work ethic, and killer instinct that would possess him to become the greatest of all time—evolved into the most oft-uttered tale in high school gymnasiums around the world. Even in venues far removed from the basketball court, the fact that even Michael Jordan was cut from his high school basketball team is used to inspire people in all walks of life to see any setback as a temporary stumble.
Still, when Michael Jordan’s name attained legendary status, Leroy Smith’s became collateral damage. Rather than sticking with the name he was most comfortable with and leaning into the identity as Michael Jordan’s childhood tormentor, Smith opted to adopt his seldom-used forename to avoid any sort of recognition, even in circumstances when it probably would’ve aided him.
“While I was working at the Asics shoe company, I went up to Nike’s campus and interviewed about three or four times for an open position they had there,” said Smith. “I had the interviews; I walked around campus. At the time I was going by Harvest, so I don’t think anyone knew the connection between myself and Jordan. When I left Asics, my friend sent me to interview for a job at the BET Network. The interview went great, but then my friend asked me later why I never showed up for the interview; they were looking for ‘Roy Smith,’ and I’d showed up to interview for the job as ‘Harvest L. Smith.’”
Leroy made up his mind that he needed to be two different people, and since Leroy Smith had been ineluctably tainted as “the Michael Jordan guy,” he adopted Harvest Smith as his business alter ego to avoid any conversations about his childhood teammate.
“For a long time, I pulled away from the story, whether consciously or unconsciously because I didn’t want my life to be a caricature,” laughed Smith. “I didn’t want to be the guy who always said, ‘You know, I played with Jordan, and my name is Leroy!’ Well what about the rest of your life?”
Smith didn’t want his life to become a caricature, but in the aftermath of Jordan’s Hall of Fame induction, that’s precisely what transpired. Nike launched a 2009 advertising campaign inspired by the tale of Leroy Smith acquiring his varsity team spot over Jordan, casting Charlie Murphy as a buffoonish distortion of Leroy Smith. The impersonation even incorporated Smith’s teenage fondness for martial arts.
The characterization of Leroy Smith as a nitwit clinging to a teenage connection with Michael Jordan is the furthest thing from the educated corporate executive who did everything he could to distance himself from the unthinkable crime he’d committed against a basketball deity. Still, the cartoonish mockery of Smith might have survived as his enduring image if someone with a penchant for storytelling hadn’t been watching that Hall of Fame induction ceremony in 2009 and hoping to examine Smith’s story more closely.
As Emio Tomeoni sat watching television at his parents’ house in Berkeley, California, he had questions. Specifically, if the man on the screen truly was the legendary Leroy Smith—usurper of Jordan’s rightful spot on the Laney varsity basketball roster—why would he willingly present himself before an international television audience just to be ridiculed? Surely, there was more to the story.
Eventually, there would be much more to the story of Tomeoni as well. At the time of Jordan’s induction into the Naismith Pro Basketball Hall of Fame, Tomeoni was in the middle stages of a trajectory that would see him become the most eclectic basketball storyteller on YouTube. However, before he began to specialize in the art of basketball storytelling, Tomeoni was a storyteller of a different kind. After graduating from St. John’s University in New York, he worked his way over to NBC Weather Plus—the weather wing of NBC News. Simultaneously blessed and burdened by a brain saturated with creative thoughts, Emio was well-prepared when the powers that be at Weather Plus expressed their cluelessness about how to fill their airwaves with the three hours of children's programming they’d been obligated to provide by federal mandate.
“I said, ‘Hey, I have some ideas!’ and then I started just dumping ideas,” said Tomeoni. “‘What if we do segments about the weather on other planets?’ ‘What if we do segments about extreme-weather-condition animals? I could go to the Bronx Zoo!’ And they loved it. And I got a camera, and that was my job for two years. Going around making up kid segments, telling these little stories. I did so well at that.”
After two years filling that role, Emio traveled across the country back to his hometown of Berkeley, and at the moment when Leroy Smith’s face and smile briefly flashed across the television screen during Michael Jordan’s induction speech, Tomeoni was employed in a video production role at TRX, the company credited with birthing the suspension training fitness market. He’d soon move to Kansas to do similar video production work for an insurance company. That’s when it struck him that he’d be best served applying his unique brand of storytelling to something that he actually enjoyed.
“At a certain point, I realized I’d been telling all of these random stories, and I didn’t want to tell these stories,” Tomeoni continued. “What kind of stories do I want to tell? And that’s when I realized there was a place for that. There’s people out there who just make basketball content on the internet. It was Dom2K and Mike Korzimba. I figured I would just do that, and use the same approach that I would use in all of these other industries, but do it for a topic that I like. And that’s when I started doing NBA YouTube and The NBA Storyteller.”
As Tomeoni’s NBA Storyteller YouTube Channel grew, it gained a loyal following of supporters who were taken in by his talent for producing and editing videos that are teeming with color, creativity, and humor. Simultaneous to this, he became known for the exploration of subjects no other basketball YouTubers had the imagination to dream up, let alone the editorial dexterity to dispense to a niche audience that’s hyper-focused on basketball.
“It’s a combination of what I actually latch onto, and avoiding the standard topics. It’s not intentional, but if a topic felt like it was of the day, then I didn’t want to do it,” insisted Tomeoni. “That was part of the concept of being evergreen. You can talk about anything in a way that is going to expire tomorrow, or you can talk about it in a broader sense, and hopefully it lasts.”
In the process of building a cult following around niche topics, The NBA Storyteller amassed a collection of video showpieces that displayed Emio’s mastery to such an extent that when he submitted his channel for Streamy Award consideration—YouTube’s way of recognizing the qualitative contributions of its top-performing channels—he received an official nomination.
To most creators whose channels had yet to crack the 70,000-subscriber mark, this recognition would’ve been viewed as acknowledgement that a channel had achieved a level of respect stemming from content that belied its subscribership numbers. But Tomeoni isn't like most creators.
“I remember with the Streamy nomination, it was early in basketball YouTube, kind of,” observed Tomeoni. “It just felt like someone wanted to grab one of these smaller channels to keep the community encouraged or something. So when we got the nomination, that confirmed it in my mind that nobody applied to [the Streamy Awards]. And then we lost, so everything was validated. They wanted a nice little channel to keep people encouraged, but I never had a real chance to win. But then I did get really upset about losing over time. I don’t think of myself as highly competitive. I like competition… but at the end of the day, I’m like, if we win or lose, that’s fine. But this one stuck with me; the Streamy one. And I said, okay, this is going to be a long road back, but we’ll be back.”
Internalizing the loss at the Streamy Awards as a slight rather than classifying the nomination as a success, Tomeoni decided to use the sting of the defeat to fuel his comeback march in a manner reminiscent of a certain professional basketball player from Wilmington, North Carolina. That’s when Tomeoni revisited his plan to explore the backstory of a different Wilmington ballplayer, and ultimately create the film that would serve as the catalyst for his redemption.
“I wanted to know, what are you getting out of all of this, Leroy?” said Tomeoni. “He’s clapping and shaking his head while Jordan insults him. Whatever is happening between him and Leroy is behind a couple more curtains. So I wanted to figure out what that was back there. In my mind, Leroy Smith did not appear to be taking advantage of being Leroy Smith.”
In the 10 years since he watched what he interpreted as Smith’s public embarrassment, Tomeoni developed the requisite skills to effectively tell Smith’s story. Tomeoni’s initial efforts to do so took the form of probing accusations, as he posted multiple videos directly questioning Smith’s motivations, and then concluded his second video—“Web of Lies”—by feigning direct telephone contact with Smith.
“In the beginning, it was tongue-in-cheek when I leaned into the conspiracy aspect, but people got really excited about it, and they asked me, ‘Did you just call him?’” explained Tomeoni. “And I thought, the way people are interested in this story of me trying to find Leroy Smith, I should actually do that. People wanted me to go down that rabbit hole, and I realized I might actually have to practice some journalism here.”
The problem was Emio needed to locate Leroy and recruit him in order to complete the project. That was a challenge that proved more daunting than preventing Michael Jordan from making the roster of a basketball team.
“He had a very low profile on social media. He’s one of those guys who had eight followers on an account that he opened up a decade ago,” laughed Tomeoni. “I had pages of Google docs of ideas of what I could do, and we were going to track down Leroy and stay outside of his building or where he worked, because I just couldn’t get him to respond to me.”
Tomeoni had help from writer and producer Ian Goldstein, who ultimately served as the assistant producer of the project. Goldstein attempted to assist Tomeoni with the outreach efforts directed at Smith.
“I was fascinated by that project, ‘Web of Lies,’” said Goldstein. “I brought it up to Emio every time we talked. It was dormant for a while, and we tried to reach out to Leroy Smith and find him, but that never came to pass.”
Because of Smith’s silence, the project sat idle for four years. That’s when Tomeoni’s afternoon was interrupted by a DM from none other than Leroy Smith, who was looking to collaborate with him. Tomeoni assumed that Smith had finally opened one of his many messages or seen one of his videos, but neither assumption was correct.
“Around mid-2023, I decided that I was going to try my hand at a podcast called ‘Lessons from Leroy,’ and I would just tell my arc so far as business and sports and life and how they all tie together,” said Smith.
Eager to gather momentum to start his podcast, Smith went through his old Twitter account, and scanned for basketball-themed channels that caught his eye. That’s when he spotted the name of one account that was impossible for a former pro basketball player like Smith to miss.
“The NBA Storyteller came up, and I said ‘Ooooo… NBA Storyteller,’” said Smith. “I had no clue who Emio—I call him ‘E’—was at that time. I just knew that he had a decent-sized following, was into sports, and I thought he was a perfect guy. I crafted an email and said I’m Leroy Smith, this is my background, and if you want to collab, let’s set up a chat and see what happens. I sent it out, and the next day I got a ping back. It said, ‘Hey, I’m interested. Is this really Leroy Smith?’ I said ‘Yeah, this is me!’ He said, ‘You won’t believe it. I’ve been looking for you for five years!’ I had no clue he had been looking for me.”
As fortuitous as the introduction had been, Tomeoni still credits his original efforts of planting enough Leroy Smith seeds around the internet to make it inevitable that they would ultimately bear fruit in the form of a meeting.
“Obviously I own a little bit of the Leroy Smith real estate online,” said Tomeoni. “It wasn’t because of any video I made, or anything that I said to him, or sent him, or referenced. The reason he found me is because he was searching for Leroy content, so that laid the groundwork for him to find me. No one thing I did broke through to him; he found me. I built a bubble around him. He didn’t know it, but he was destined to end up with me.”
Smith and Tomeoni were now in contact and in agreement they’d work together to tell Smith’s story, but Leroy had no idea who he had agreed to work with. That’s when he decided to sit down and watch some of The NBA Storyteller’s content, while taking great care to avoid everything that his new collaborative partner had already produced about him.
“I watched nothing that he did on me,” insisted Smith. “In my mind, I wanted to have a clean slate. I went through all of E’s other videos on YouTube, and then I called him back and I told him ‘I love your style.’ I love the way he presents all sides of a story and gives his take on it, and I loved his graphics and how he puts everything together. It wasn’t the Hollywood, slick, A-B-A type of format. It was this real eclectic way of thinking about things, and I thought that was really cool.”
The end result was the most thorough telling of Leroy Smith’s story, treating him for the first time like he was a main character in his own right, and not as an accessory to a superhero’s origin story.
“Goldilocks and the three bears is a classic story, but what happened to the three bears? Nobody knows,” said Smith. “The story doesn’t follow them, but they were probably okay. That’s why E was so great. He wanted to know what happened to the other guy. The documentary completes the other side of the Michael Jordan-Leroy Smith story.”
With Goldstein’s help, Tomeoni completed the necessary series of interviews with Smith, and then edited the project together. When it was finished, "The Myth — A True Story of Michael Jordan & Leroy Smith” dedicated 80 minutes to explaining what it’s like to be cast as the unwitting villain of perhaps the most famous motivational tale in sports history.
“There are plenty of kids who’ve heard that Michael Jordan got cut and didn’t make his high school team, and that bit of inspiration pushes those kids over the hump,” said Smith. “It gave them hope that they could do it because Michael did it. And they’re kind of told that this guy Leroy Smith was a motivating factor in helping him to make it. So when I look at it from that perspective, I feel like I’m playing a major role in helping people get to the next level… as long as the story is told from that perspective.”
But the offense Smith takes is when the story is not told from that perspective, and when he is cast as both an arch nemesis and an eternal punchline based on an event that he was an innocent bystander to when he was barely 15.
“A lot of kids are kind of told that this guy Leroy Smith was the antithesis of Michael,” Smith elaborated. “A lot of people look at it from the standpoint that the story would be better if I turned out destitute or lying in the gutter. It’s almost like they want to hear that Leroy failed in life, like I was actually the villain of the story. But that’s usually not how a true story goes. There’s so many layers to a true story. Any person can be an also-ran character in someone else’s story, but they’re the leading character in their own story.”
The unveiling of “The Myth” was a triumphant moment for both Smith and Tomeoni, but it wasn’t the last. Tomeoni submitted the completed project to the judges of the Webby Awards for consideration, offering it as a candidate for the internet’s highest creative honor. The submission was another step in the redemption arc that Tomeoni had foreseen when he first envisioned the project.
“When Leroy and I actually made contact, and he was enthusiastic about talking to me and working on a thing, I pinned it in my head,” said Tomeoni. “I said okay, you’ve got the Emmys, and then other than that, what do you do for content that isn’t on television? The Webbys seemed to be the thing. I wrote it down in my plan that we’ll complete this, we’ll submit it to the Webbys, we’ll win the Webbys, and that will be our redemption for not winning the Streamys. I never let that go.”
Even to those around him, Emio’s insistence on avenging this perceived slight ironically evoked memories of the single-minded determination of the basketball player whose overpowering drive had inspired the Leroy Smith story to begin with.
“It makes a lot of sense that Emio felt that way and followed through with it,” added Goldstein. “I know Emio can struggle with doing things sometimes even though he churned out so many amazing things for the channel. It’s funny, because the first person I think of is Michael Jordan in this way. If you wrong me, I’m really going to get vengeance, and in Emio’s case, it was winning a Webby, which I would argue is better than a Streamy.”
While the impulse that sparked the Webby Awards triumph was Jordanesque, the path to victory was better suited to the clear underdog role that Smith occupied in relation to Jordan ever since his name was first uttered on the set of the “Michael Jordan’s Playground” home video release in 1990. That’s because even when “The Myth” received its official Webby nomination, its field of competitors included projects from Great Big Story, USA Today and The Washington Post.
It seemed unfair to even imagine what was essentially a small, one-man operation could wrest the Webby trophy away from iconic media brands with large, well-funded production teams. All the same, on the day the winners were announced, Tomeoni checked the Webby Awards website, and saw that “The Myth” had overcome the odds and won the Webby for Best Sports Video or Film.
“I exhaled, and I hadn’t realized I’d been holding my breath. Then I just kept it to myself,” recalled Tomeoni. “Two hours went by. I didn’t text anybody. I just made coffee. I made breakfast. I was just happy. I was in the moment. I was appreciating the sun through the window. Then I went back to work on my next project, and it felt great.”
The win allowed Emio to appreciate the challenges he’d endured, from the moment he first brainstormed the project, to the night five years later when he sat among fellow Webby Award winners inside Cipriani Wall Street.
Tomeoni, Goldstein, and Smith at the 29th Annual Webby Awards
“When I look back at what the version of me in the past did to ensure my success in the present, it helped me to appreciate my efforts more,” explained Tomeoni. “Through the process, I wasn’t accepting any of the lessons, but looking back on it, it reinforces something that I tell my kids. There are a billion versions of you over time. They’re all lined up, but they’re on your team. Being able to connect to them on your timeline is powerful. Once you have a connection to those versions of yourself, you’re gaining a little bit more control of time.”
Similarly, Smith, who’d spent four decades trapped within someone else’s story, is finally able to view the entirety of the experience as a long-term positive. In the end, the documentary and Webby victory freed the teenage version of Smith from a figurative form of solitary confinement, where the legend of Michael Jordan served as his eternal warden.
“I was over the moon, because now it was an opportunity to smell the flowers and embrace the story,” said Smith. “It’s okay to be the dude that beat out Jordan, and I’m going to bask in this for however long it lasts. I do see winning the Webby as an exclamation point, and a starting point. Now people know my full story. It is a great part of my life. It’s not the end part, but it’s a great part. It’s a chapter in the book that you can enjoy before you move on to do something else.”