Updated August 12, 2022 at 3:05 p.m. EDT|Published August 11, 2022 at 10:49 a.m. EDT
GARFIELD HEIGHTS, Ohio — Ashton and Henry Jolly IV had already posed for a handful of photos with giddy elementary school kids by the time the NEO Boys National Showcase began on a Saturday morning in late June. The twins had been advertised as headliners on social media by event organizers for weeks, and their father, Henry Jolly III, entered the gym with every promotional material he could carry, a black duffel bag full of gear that included mouth guards, knee pads and arm sleeves provided free by prospective sponsors, along with headbands stamped with the personal logo he created for his kids, “Jolly Boys.”
They had traveled more than a thousand miles from their home in suburban New Orleans to this high school gym outside Cleveland, and in case anyone might not recognize his 9-year-old twins, Jolly wore a neon-colored jersey emblazoned with the words “Born to Go Pro,” the family’s official brand and credo.
When the camp began, the director, Sonny Johnson, called the hundreds of youth players to center court for an introduction. “The Jolly twins are in the building!” he yelled through a microphone, and Ashton and young Henry stood up. Johnson placed a $100 dollar bill on the floor and told them it was theirs if they could hit a half-court shot. Their father jogged onto the court and whipped out his cellphone to begin recording. “I’ve got to get this,” he muttered to himself.
Both twins missed their shots, but it was still footage their 39-year-old father could use for the online documentary series he has been developing around their brand, along with a basketball camp and a clothing line. As the economics that surround youth sports have exploded, some parents have fashioned themselves as de facto agents for their young athletes, entrepreneurs who are aggressively promoting their children and priming them for potential endorsement deals as they develop.
Name, image and likeness opportunities, prohibited for so long for amateur athletes, quickly reshaped the college sports landscape, and their influence and financial reach already have started to trickle down to elementary school age, as youth teams, coaches and parents see endless moneymaking opportunities without any regulation or more encumbrance. But while the marketplace is shifting, there also remains uncertainty among stakeholders where it ultimately is headed.
Jolly sees a shifting environment ripe for exposure, and he’s intent on his kids becoming the youngest players in the country to land a lucrative NIL deal.
“Nowadays, in 2022, they looking for the next big thing. And I believe we are that. And when an opportunity presents itself, we’re going to jump at it,” he said.
Jolly has taught his boys that everything they do is part of their brand — from the way they play to their shoulder-length brown braids, which their father has made clear must be allowed by any middle school or high school coach recruiting them. He curates their social media feeds, spends hours editing their YouTube highlight videos and sometimes wears a T-shirt he made with the logos of seven youth basketball rankings websites, all of which have rated his sons the top second-graders in the country.
“That’s part of my strategy: Build their name up, build the expectations up, build their skills up, build their bodies up, so that by the time they get to high school, these companies are going to pay them to play,” Jolly said. “We want to do it as early as possible. I believe we’re going to be the pioneers.”
‘Rapidly changing environment’
For decades, the nation’s top basketball players were prohibited from pocketing any money until they turned professional, which usually couldn’t happen until after at least a year of college ball. But new state laws over the past year-and-a half have upended the rules at the collegiate level, and suddenly there are a lot more hands trying to get a slice of an increasingly lucrative pie.
Throughout the weekend, Jolly would post a handful of photos and videos featuring his sons on Instagram, but there was one trophy that stood out: a selfie with Armando Bacot Sr., whose son, Armando Jr., is a star forward at North Carolina and who weeks earlier had withdrawn from the NBA draft to accept a handful of NIL deals reportedly worth at least $500,000.
Bacot Sr. was in attendance to watch his other son, King, who some consider one of the top fifth-graders in the country, and the twins finally posed for a photo with both. “I’m a big fan,” Bacot Sr. told the Jolly kids as he shook their hand. After they ran off toward the concession stand, Jolly stayed to pick Bacot Sr.’s brain on how to build his own children into NIL stars. He rubbed his hands together after the conversation.
“He told me: You’re promoting them right. They’re playing up. They look good,” Jolly said.
More than a dozen states have sanctioned NIL in high school, although deals are typically reserved for teenage phenoms with large social media followings. Mikey Williams, a senior guard from San Diego with nearly 6 million followers combined on Instagram and TikTok, inked deals with Puma and Excel Sports last year and has an NIL valuation of $2.6 million, according to the recruiting site On3. And Jada Williams, a five-star recruit from Missouri who is still only a junior, has already signed deals with Spalding and Dick’s Sporting Goods. Nike completed its first NIL deal with a prep athlete in May when it reportedly signed high school soccer stars Alyssa and Gisele Thompson, sisters who play in California.
“It’s a really rapidly changing environment, and it’s really interesting to see this trickle-down effect, from NIL in college, to kids building their brands, to parents positioning their kids to have success at the next level,” said Travis Dorsch, a professor at Utah State University who researches youth sports. “It used to be we were just focused on parents being at the games and practices and training and how involved they were and the types of conversations they had in the car or around the dinner table … whereas now they’re sort of turning into agents for their kids.”
The twin’s mother, Ashley Jolly, gave up her career as a telecommunications engineer and started her own day care in suburban New Orleans, which afforded her a chance to be around her kids more and have an active role in their basketball careers.
“We didn’t see this happening,” she said, and while she supports her sons building their brands and pursuing professional careers, she sometimes worries about the pressure they are facing. Her husband earned a master’s degree in counseling from the University of Holy Cross in New Orleans, but Ashley also keeps the pulse on how her kids are feeling, making sure the twins don’t get overwhelmed.
They travel up to three times a month, spending a couple thousand dollars each time, which sometimes tournament and camp directors alleviate by picking up room and board and other expenses. But there are other stressors: Jolly often worries about his kids doing anything other than basketball on trips because they might get tired or injured for competition — “He is over-the-top basketball,” Ashley said — and when the boys lost at the AAU national tournament this summer, everyone was emotionally drained.
“It’s a crazy world. It is. I would never thought it was this, especially this young. Sometimes it is really stressful for Henry and I. We literally are stressed,” she said. “I’ll just be like, ‘Henry, I can’t deal with this; I have stress from my job.’ Some days I have to tell him: ‘I can’t talk about basketball right now. I just can’t. I’m tapped out.’ ”
Ashley said the family has lost friends because the Jolly boys have defeated their children on the court. Ashton will sometimes take it personally when a kid scores on him, and the younger Henry has started to follow suit.
“I honestly believe my sons have started something that sparked every child their age and under to step their game up,” she said. “Every time my kids step on the court, they have a target on their backs, so much so, some kids won’t be kids. They won’t come up and talk to them. … They are thinking like little professionals.”
People will sometimes tell Jolly that he reminds them of LaVar Ball, the outspoken father who built his Big Baller Brand around his three high school sons, two of whom now play in the NBA.
“I was doing this before I even knew who he was,” he said as he watched his kids warm up for the camp.
‘None and done’
Jolly posts around a half-dozen times each day on his Instagram account (handle: @nbacoachjolly), where he has more than 6,000 followers, along with a separate account for just the boys, which sports another 3,000 followers. His YouTube page is filled with highlight footage — some videos have garnered thousands of views — and features a new YouTube docuseries called “Born to Go Pro,” which shows clips of the boys training and talking about their favorite NBA players.
“Whatever makes sense, that is good for the brand. That is good for their brand,” he said. “I’m doing this for them.”
He has his eyes on other ways to make money: Last year, Overtime, a digital sports media company, started a high school league that offers kids six-figure salaries. Even though those players must forfeit their NCAA eligibility, Jolly is determined to get his kids into the league before they turn pro.
On the second day of the camp, Ashley and the couple’s 6-year-old son, Hunter, both showed up in gray Jolly Boys-branded T-shirts. The front read: “None and Done.” And on the back, the word “College” was crossed out. Her boys already have their futures mapped out.
“I want to play in the NBA for a long time,” said Ashton. “I want to make a lot of money.”
“Play in the NBA,” added the younger Henry, “and be a Hall of Famer.”
Back at their home outside of New Orleans, their father has also developed his own camp around the brand, which can be a lucrative endeavor for some stakeholders in the sport. A few hundred kids had paid their $265 entry fee for the NEO Boys National Showcase, which boasted a well-stocked concession stand and a merchandise store selling $50 shorts printed with an assortment of emblems: Kobe Bryant’s nickname, Chucky the Doll, The Joker — along with T-shirts, hoodies and backpacks. There were evaluators in the stands compiling scouting reports on the top kids, along with a film crew shooting mixtapes, which could be bought online later for $179.99, according to the camp’s website.
Jolly still conducted all of his own filming, as he had all summer as his boys traveled the country for tournaments — Miami, Orlando, Dallas. At the camp in suburban Cleveland, even though second-graders are below the age threshold, the Jollys were invited to compete against the best third- and fourth-graders in the country. Their father was also taking notes for himself, because for years he has been trying to grow his own camp into the type of event that he often brings his own boys to. A recent stop on their year-long camp circuit attracted more than 600 players and cost $200 apiece.
“And my kids were the headliners on it. You do the math … over 100,000 dollars on a weekend,” he said.
Jolly wiped the dust from his own Iverson shoes before his kids began their first scrimmage of the camp, as if he was ready to play himself. His kids wore gear provided free from companies their father hopes will one day become paid sponsors, including Mighty Mouth Guards and CoolOMG, which he said sent the boys free arm sleeves and knee pads this summer.
Johnson ventured over with a cordless microphone to provide colorful announcing to the hundreds of spectators in the gym. Ashton carved up the defense with a coast-to-coast layup, and young Henry followed with his own step-through layup. “They’ve been doing this for years!” Johnson yelled. “They’re as good as advertised!”
Still, their father wasn’t satisfied. The twins’ team trailed by 11, and even though Ashton hit a deep three-pointer — “I didn’t know you were that good!” Johnson yelled over the PA system — the younger Henry struggled. His father pulled him aside after the game.
“You’re going to miss shots. That’s not the problem. The problem is that you’re not playing hard,” Jolly said, before helping his son take his shoes off and giving him a Lunchables to eat. “Everybody is going to know who you are. … You have to be a killer.”
A new breed
Jolly’s own basketball career didn’t turn out as planned. He played high school ball in New Orleans and had a stint as a college walk-on but quit before the first game to start his own business breeding American Bullies, a cross between pit bulls and bulldogs.
Jolly bought his first dog from the rapper Curren$y for $90 and a pack of Starbursts, he said. He had a part-time job making $5 an hour at Kids Foot Locker, and while his friends were using their money to buy the latest Jordan or LeBron shoes, Jolly saved to buy dogs and kennels, marketing them with online videos and at dog shows. He sold over $1 million in dogs, he said, enjoying enough success to buy his first house at 22 and eventually start a family with Ashley.
“I learned marketing on the fly from the dogs. I was always promoting the best stud in the world,” he said. “It’s the same concept with the kids … I know how to get the name out there. On YouTube, we have some dog videos. I have one video that has almost a million views on a dog. He ain’t on a unicycle, he’s just walking around. Like, look at how great that dog looks? Now I have people with actual talent. I just know it’s a matter of time before we blow up, because we have talent.”
He put a ball in the twins’ hands shortly after they were born, teaching them how to dunk on a plastic Little Tikes hoop. By age 2, they were dribbling. By 3, they were shooting on 10-foot hoops. By 5, they were learning offensive sets. And by 8, they were at the doctor discussing growth charts, because Jolly, who is 5-foot-10, is hoping they will grow a few inches taller to be reasonably sized guards in the NBA.
At 4-10 and 4-11, both Henry and Ashton are undeniably talented. They work out roughly 35 hours a week, doing two-a-day sessions in the summer that involve basketball drills and body-weight exercises. When they landed in Orlando late on a Friday night for the AAU national tournament this summer, their father found a high school gym so they could work out after midnight before their games the next day. They each must make 400 shots daily, per their father’s rules, and when he’s not around, they play against each other so that one can work on offense while the other works on defense. “That’s the advantage I have,” their father said. “Iron sharpens iron.”
When New Orleans shut down for the pandemic, Jolly started his own local AAU team and began traveling to nearby states that would allow them to play. Because New Orleans had closed gyms and local parks, he hunted for outdoor courts across the city, traveling with a ladder, drill, nuts and bolts and a rim, conducting hours-long practices for several months. The kids have other interests — riding bikes, jumping on the trampoline, watching movies — but basketball comes first.
“I just like playing basketball all day,” Ashton said.
Next year they will home-school for the first time, until their parents decide what their middle school future might be. It will give their father more flexibility to balance his day job offering mental health services across the city while coaching and promoting the kids.
Taking their shot
Before their final scrimmage during the camp, the team’s coach wanted to put one of the Jolly twins in the starting lineup and keep the other on the bench. Their father rushed over to tell the coach that they were a package deal and that they would both begin the game on the bench.
They entered the game looking identical from head to toe: same Kyrie Irving Nikes, same emoji-patterned camp shorts, same braids. The only way to tell them apart was their blue and red Jolly Boys-branded headbands. They looked to pass to each other — and only each other — throughout the game, setting one another up for an array of three-pointers and running layups. When the younger Henry got a steal and went coast to coast, Johnson perked up with the microphone again.
“The No. 1 second-grader in the country! These boys are tough!” he yelled as Drake blasted on the gym speakers.
With their team down by three points with 29 seconds remaining, Jolly called from the sideline for the younger Henry to take the ball out and pass it to his twin brother, overriding any directive the coach may have given. With so many kids and their parents starving for a highlight to put on a mixtape, it was the only way to ensure they would take a potential game-tying shot. Henry followed his father’s order and found Ashton, who used his lightning-quick speed to get past three defenders and pull up for a three-pointer.
The ball bounced off the rim. Ashton put his hands on top of his braids and shook his head. His father stopped filming, and as the horn sounded, he told his boys, “Good game.” By the end of the weekend, Jolly would have another highlight video ready to release, labeling it: “Jolly Twins PROVE why they’re the #1 second graders in the country.”
After more than a dozen hours in the gym, the boys finally stopped dribbling and took off their shoes. They posed for a few more photos and squinted as they emerged outside, the early evening sun beating down. Jolly carried the black bag full of his kids’ gear, and before putting it into their black rental SUV, he was stopped by another star-struck father. The twins stood by his side and listened.
“Man, my kid is 4, and I’m showing him their videos,” the parent told Jolly. “I love watching them.”