Words: Twig Spensley 2021-12-01 07:10:30

“These kids wanted to hang with Lupe at this Minneapolis, spot, but they kept running away as they got close. They were definitely more local than us and were curious what we were up to skiing in the street. Eventually they worked up the courage to talk to him and found out that Lupe’s actually a pretty nice guy.” Photo: AJ Dakoulas
Hagearty had perhaps the biggest moment of his career in 2021 with an appearance in the X Games Real Ski competition and a shot at an X Games medal. While his all-street segment, filled with classic style and timeless tricks, did not put him on the podium, he showed a national television audience that there was still a place for the style-heavy street skiing that gave birth to the more technical and competition-focused freeskiing of today. After years spent quietly earning his place among street skiing’s original superstars, Hagearty is now helping to keep the streets in the spotlight.
Hagearty was a child of winter. Before he could walk, his parents were putting the toddling Hagearty between their legs and skiing down Burke Mountain, VT. The Vermont family cabin was a snowy escape for Hagearty and his 15 cousins. As a kid, he was into all kinds of action sports—biking, skateboarding and inline skating as well as skiing and snowboarding. But it wasn’t long until his cousins introduced him to freeskiing. An older cousin, Patrick O’Gority, became his regular ski partner.
“I remember Lupe and I both landing our first 540s on the same run then following up the very next run both landing our first 720s,” O’Gority says. “As a skier, [Lupe] has always had a pretty natural style. He is a few years younger, so me and my cousin Justin were always pushing him a little bit. He knew if he didn’t hit a certain jump or rail that he would be hearing about it from us.”
It was the kind of familiar peer pressure that drove a young Hagearty to not only push his skiing, but also to immerse himself in the freeski world. In addition to honing his skills at Burke and Ski Sundown near his Connecticut home, he had his first exposure to the wider ski scene at the IF3 Festival in Montreal in 2010.
“There was crazy energy and stoke, the vibe inside the theater was incredible,” he says. In many ways, the then-16-year-old had stumbled into a golden age of ski cinema, when production companies had substantial budgets, premieres were multi-day events, and IF3 was the biggest show (and party) around. “It was the first time I saw pro skiers in real life and I was freaking out,” he says. “I vividly remember sitting next to Will Wesson and Andy Parry in the theater in disbelief. After that weekend in Montreal, I was dead set on becoming a part of the community and getting myself up on the big screen.”
The following year, in 2011, his paternal grandmother dipped into her retirement fund to send Hagearty to Waterville Valley Academy in New Hampshire for his junior year of high school. The move gave Hagearty the chance to focus on his skiing without distraction while making connections with other rising pros and the ski industry at large.
But it wasn’t until 2013 that he got his first big break. Hagearty snagged a few shots in the Dakine team edit alongside Tanner Hall at Windells Ski Camp on Mount Hood, OR, that summer, then was featured in a La Familia edit with Hall and Ahmet Dadali. Though he didn’t actually film with the legendary freeskier, Hagearty decided to reach out to Hall the following fall.
“I saw he was still around Keystone, CO, so I sent him a Facebook message telling him how stoked I was to be in two edits with him,” Hagearty says. Hall, quick on the draw, asked if Hagearty wanted to link up and film. “I ended up filming and chilling with T-Hall every day for the month of November for his Inspired series ‘Winter Jungle.’ I’m getting goosebumps just thinking back to that experience—a huge turning point in my career. It felt like my dream of becoming a pro skier and filming for ski movies could happen.”
The reality at the time read a little differently. Very few “pro” skiers make a living from skiing, and even fewer do so fresh out of high school. To support his newfound momentum, Hagearty painted houses during the week and catered on weekends. But his month with Hall would prove formative. Hagearty cites the former X Games champion’s hard work and dedication as well as Hall’s longevity in a sport that has very few veterans as setting the example for his own skiing. Through Hall, he also met producer Eric Iberg, which eventually led to Hagearty’s first film project, a webisode series with Inspired Media called “The Style Files.”
“I really feel that is what put me on the map,” Hagearty says. “Iberg helped me understand the logistics of the ski-film world. He showed me how you can hustle to make things work.”
That hustle typically involved putting his body on the line nearly every time he clicked into skis. Hagearty broke his pelvis while skiing street. Shortly after recovering, he dislocated his elbow on another urban feature in Idaho. Out of money, he relied on a friend’s airline points to get back to Salt Lake City, where he drove his manual-transmission car with his arm in a sling all the way back to Colorado. He remembers the pain and swelling becoming unbearable and then getting stuck overnight on Vail Pass. “That was one of those times where I would ask myself, ‘What the hell am I doing? Is this worth it?’ Dealing with injuries and being really broke in the early years can wear you down. It’s tough to put your heart and soul into something and feeling like you’re not getting anything back at times,” he says.
Hagearty’s work in the streets had, however, caught the attention of another freeski icon, Tom Wallisch. The X Games gold medalist known for his refined street style took Hagearty under his wing, giving him the chance to film for Wallisch’s new production outfit, Good Company. Those trips helped raise Hagearty’s profile and also reinforced his dedication to stylish skiing.
“Watching Wallisch and the afterbang era as a young skier was without a doubt what initially brought the realization of style to my attention,” Hagearty says. “When I first got into skiing, I was so unaware of everything going on in front of my eyes. Watching Wallisch ski made me consciously think about the way my skiing looks.”
Staying true to their own visions of skiing is a modus operandi that binds Hagearty, Hall, and Wallisch. For Hagearty in particular, that has meant that style matters above all else.
When talking about style, Hagearty likes to reference a Charles Bukowski quote: “Style is the answer to everything. A fresh way to approach a dull or dangerous thing. To do a dull thing with style is preferable to doing a dangerous thing without it. To do a dangerous thing with style is what I call art.”
Even with the pressure of X Games Real Ski bearing down on him and the knowledge that the rules had changed to allow park and backcountry shots in addition to what had traditionally been street footage, Hagaerty stuck to his art—a brand of street skiing that fused the gap between old and new.
Hagearty’s contest entry turned heads in freeski circles. Forums on popular freeskiing sites like Newschoolers began to openly disagree with the addition of park and backcountry shots to the street-style video competition, citing Hagearty’s video as an example of what the contest was truly about. Many judges echoed the sentiment.
“It felt really good to finally get the nod from the judges, who are some of the best street skiers in the world,” Hagearty says. “To have been at it for a long time and finally find myself on the big stage was very rewarding.”
These days he feels like he doesn’t have too much left to prove. Recently Hagearty made the move from Colorado to Salt Lake City, which has become the epicenter of freeskiing. Wallisch is there as well and they still ski together occasionally. They even linked up on the East Coast and hit some spots together while Hagearty was filming for Real Ski.
“Urban [skiing] is more about perseverance than anything else,” Wallisch says. “Lupe had that motivation to work as hard as possible. His motivation is as great as anyone I’ve ever met.”
Hagearty, now 29, spends much of his time skateboarding and playing guitar, but his dedication to skiing in general‚ and street skiing in particular, remains strong. He wants to continue filming, though he’s not sure another X Games run is in the cards. The platform was a great launchpad, he says, but the pressure took away from the overall experience, and it isn’t the reason he got into the sport in the first place.
“I just want to enjoy filming and put out videos I’m stoked on,” he says. “If people like them, dope. If not, that’s cool too.”
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