On a recent Sunday afternoon in Midtown, Steve Rodriguez stood in the street, his hand raised in the winter sunlight, watching for traffic and security guards. His skateboard was tilted over on the sidewalk to make a small barrier — a visual cue for walkers to be cautious. He scanned the street, the sidewalk and a plaza up ahead, where a young man was waiting with a skateboard in an empty fountain.
Mr. Rodriguez dropped his arm. “Go!”
Shiki Rodriguez, 12, jerked into motion. He sprinted forward, jumped onto his board and raced across the fountain, then hit the upturned lip, launching himself into the air. He flew over the ground with his eyes on a bench, his anticipated landing spot. But he landed off balance, and the board shot out as he fell backward.
Steve Rodriguez, the lookout and Shiki’s 51-year-old dad, jogged over, intercepting his son’s board. “That was a hard slam,” he said. “You OK?”
“Yeah,” said Shiki, taking back his board.
A well-dressed woman and her dog stepped around Mr. Rodriguez’s sideways board, giving both skaters a wary look.
Mr. Rodriguez knew that they didn’t have much time before security inevitably arrived to eject them, and he urged his son to get back in the fountain and try again.
“This is a kick-out spot,” he said, retaking his place as lookout. “I’ve never skated here more than 10 minutes.”
Mr. Rodriguez has navigated countless situations like this since the 1980s, when street skateboarding — an aggressive mutation of its Southern California counterpart — emerged in New York.
Skaters of the day’s session spanned two generations, all rolling happily through the plaza: Mr. Rodriguez, Shiki, and two of Shiki’s old skate pals, Ari Misurelli, 11, and Jiro Platt, 16. Their dads were Joe Misurelli, 44, and Jeremy Platt, 48.
Ari’s dad was raised in Wisconsin, where there were no skate parks. “There was only street skating,” Mr. Misurelli said. “I grew up dealing with cops almost every day.”
The dads have never let their sons forget how good they have it. New York now maintains no less than 40 Parks Department-sanctioned skate parks, miles and miles of poured concrete and obstacles designed specifically for skateboarding.
The sons know this history, some of which is the stuff of skate legend, like the Brooklyn Banks, which Mayor Eric Adams announced this week could be refurbished as part of a proposed $160 million development. (“I’ve heard of it,” Ari, who was born in 2012, said of the Brooklyn Banks.)
Sometime around the early 1980s, downtown skaters discovered Red Brick Park, as the Brooklyn Banks was officially known.
The spot was a basin of undulating brick under the Brooklyn Bridge, with Jersey barriers that were perfect for wall-riding. The scene was industrial and deserted. Inside the bridge anchorages were a chop shop, a crack market and a homeless encampment. Mr. Rodriguez grew up skating there and is now part of the team helping rebuild the Banks.
That skateboarding has changed a lot since then, Mr. Rodriguez said, “is a total understatement.”
In his three decades skating the New York streets — as a respected athlete, consultant, business owner, advertising executive, skate park designer and activist — Mr. Rodriguez has probably seen as many social, cultural and financial shifts as anyone.
He was there when a tiny downtown skate shop named Supreme opened in 1994; the brand was recently sold for $2.1 billion.
Skaters are now Olympic athletes, sponsored by billion-dollar corporations like Nike and Red Bull. New York’s most famous pro, Tyshawn Jones — recently seen on the cover of Thrasher magazine doing a kick-flip over subway tracks, something previously possible only in video games — is represented by DNA Model Management and is a spokesman for Tiffany & Company.
Mr. Rodriguez also recalls when the Brooklyn Banks were suddenly closed in 2004, and again in 2010, which was around the time he won a grant from Nike and used the money to design and build a park nearby with help from the Tony Hawk Foundation. That park, now known to skaters as LES, is New York’s most famous, and a popular meeting site for the dads on Sunday mornings, though on this day they were sticking to street spots.
LES is just one of the city’s dozens of official skate parks, a reminder that skateboarding is here to stay — but only, it seems, within certain boundaries.
“It’s important to have a safe, well-designed space where there’s the freedom to practice,” Mr. Rodriguez said.
And yet, no one is drawn to skateboarding for its safe, well-designed spaces.
“Skate spots are a hundred times better,” Shiki said. “You go to one spot and it’s not like anything at a park.” For him and his friends, improvising is key. “You can make it better. Like, if there’s a broken chair, you can use that.”
In fact, this is exactly what Shiki and his friends did the day before.
“That’s an individual experience,” Mr. Rodriguez said. “You utilize everything in that environment. You create something. And you will probably never have that experience again, so it’s unique.”
Something in the corner of the plaza caught Mr. Rodriguez’s eye, and he turned to see Jiro soar over a construction cone, a perfect backside flip.
Jiro moved with the grace of a figure skater, and, like all great athletes, he seemed to occupy a higher space than those around him. Each flip and spin looked natural but had clearly been dissected, tweaked, tinkered, perfected. Every trick was a little faster, higher, harder and smoother; even the hum of his wheels was different.
Jiro left school mid-pandemic and probably won’t return. He grew up on Canal Street, skating at LES, where he met Mr. Rodriguez, who saw Jiro’s talent and introduced him to a representative from Volcom, a skate apparel company, which hooked him up with free gear and clothes (a low-level endorsement known among skaters as “flow”). Soon Nike came calling, then Red Bull, which gave Jiro a small salary and provided a consultant to advise him on social media and quarterly earning goals. He was 13.
Still, professional aspirations aside, like Shiki, Jiro prefers the street.
“Of course, I’ve got to skate park sometimes,” he said. “That’s essential to kind of hone your skills.”
His dad, Jeremy, who grew up skating in Texas, where football was everything, is thrilled about Jiro’s opportunities. But Mr. Platt also has conflicted feelings about his son skating kick-out spots, which often means brushes with security.
“Avoid confrontation and be respectful,” he advised. “These guys are just doing their job.”
The group moved to the other side of the plaza, directly across from the 23rd Police Precinct. Facing a row of mini-cruisers, Ari, who was in sixth grade and lives in Brooklyn, stood at the end of one long block of marble. In front of him was another block; between the two, a gap.
Ari wore look of stern focus and clothes flowed from Volcom and Adidas.
His dad hung back with Mr. Rodriguez. They talked about street skating and the hazards of being kicked out of public spaces. “I grew up dealing with cops almost every day,” Mr. Misurelli said, adding that he raised his son to be respectful and to avoid confrontation.
“They’re not legally allowed to touch us,” Ari said.
“Kids nowadays know that,” said his dad. “Back then, they could touch you.”
Standing atop the long marble block, Ari jolted into motion, rolling to the end and popping a kick-flip over the gap. He landed on the next block but fell, sliding upright in a seated position, the way good skaters fall. He tried again. Then again. And again, sliding off the block and spilling onto the ground. He looked displeased but patient.
New skaters joined the group. Some had their phones out to shoot video.
Ari stepped up onto the marble.
“You got that, Ar!”
He threw down, popped, flipped, landed clean and rolled away — off the block and past the fountain.
Skaters tapped the tails of their boards on the pavement, a universal sign of appreciation.
Jiro and Shiki gave their friend a moment to bask in the achievement, then went after him, convening in something of a hopping huddle, hitting one another on the head.
“That was the last try,” Mr. Rodriguez observed.