Henry Sildaru: The Crystal Globe Interview

There are few people in the world of Freeskiing who have had more of their career - and, indeed, whole life - documented, dissected, and debated than Estonia’s Henry Sildaru. The younger brother to superstar Kelly, the Sildaru sibling’s entire life on skis has been spent in front of a camera lens - which, for Henry, meant many years playing a supporting role as the endearing grom while Kelly ascended the ranks to take a place amongst the Freeski elite. 

While Henry’s ascension has been perhaps slightly less meteoric than his sister’s, the extra time spent earning his place amongst Freeski’s elite was indeed time well spent, as the 2025/26 season saw Henry finally graduate from promising youngster to top contender. 

And he picked one heck of a season to take the biggest steps of his career. After earning his first career World Cup podium in Slopestyle at the U.S. Grand Prix Aspen Snowmass, Henry went on to shock the Freeski world with a silver medal in Halfpipe at the Milano Cortina 2026 Olympic Winter Games in Livingo - just .75 points behind gold medallist Alex Ferreira (USA). 

And he was not done yet.

Coming off his Olympic silver, Henry kept the pedal to the floor through the remainder of the World Cup campaign, nabbing third place in the Tignes Mountain Shaker Slopestyle, and then capping things off with a double podium performance at the World Cup Finals in Silvaplana, earning second place in Slopestyle on Saturday before landing his first Halfpipe World Cup top-3 on Sunday with another second place finish. 

And what did all that get him? Well, only the Freeski Overall Crystal Globe as the top dawg for the men’s season across all of the FIS Freeski World Cup. 

Safe to say that Henry Sildaru has made good on the potential for greatness that has been evident throughout his life on skis, and if the Big Air results start coming for the young man who is set to turn 20 on 26 August, it’s going to be tough for anyone to touch him atop the Overall ranking for years to come. 

We caught up with Henry last week to get his perspective on an incredible 2025/26 season. Check it out below…

FIS - First up, where are you right now and what have you been doing since the 2025/26 season ended?

Henry Sildaru - At home, with my family. In that sense, it’s nice to be back home during the summer. In autumn, when my dad and I set off in search of snow, we are usually away from home for 3–4 months at a time, so at the end of the season it’s nice to come back home for a while. The closer the end of the season gets, the more strongly, strangely enough, I start thinking about my own bed. You would think that after all these years you would get used to different hotels and beds, but no – my own bed still smells different, the mattress has exactly the right firmness and the right width. Most important, of course, is family. We are a very close-knit family – grandparents, and now also my little brother – and after being away for a long time, it’s nice to do different things together with the family again.

After a short break, I am slowly preparing for the new season at home. Gym, lots of cycling – one of my favourite summer activities is riding my mountain bike in the forest.

Years ago, my grandfather used to ride his bike on his own and participate in cycling marathons all over Estonia. At some point my grandmother joined him, and today it has become a nice weekend activity for the whole family. Even last year, all three of us – me, my grandfather and my dad – started together in the long-distance races. And we seriously competed against each other. It wasn’t uncommon for my grandfather to beat both of us. He does more cycling training as well.

This year, my grandfather and I have been doing the long distance together, and at the first race of the season I immediately got beaten by my grandfather. So I had to get myself into shape, and now I have been coming out on top more often. My little brother has also been taking part in the races – my dad put a Thule baby seat on his bike and rides the shorter distance with him.

So overall, the summer has been quite relaxed – a bit of rest, slowly getting some training in, and cycling together with the family.

FIS - You're pretty stoic on hill - incredibly so when you consider that you're still just 19 years old. Is that an Estonian thing, or is that particular to yourself and the already significant length of time you've spent in the freeski game?

HS - I think some of it is definitely an Estonian or Estonian people thing. But you can look at it from several sides. So I doubt the reason is simply that I have been in the freeski world for a long time. I think it is probably more down to my character.

Quite a few fellow competitors (other skiers) have asked why I never, for example, raise my hand after a successful run in competitions. I have even been advised that I should – that it would give the judges a visual indication that the run went well. I have thought about it, but I would rather just stay true to myself. It doesn’t mean that I’m not happy when I have a successful run. Quite the opposite. It’s just that if completing the run successfully was the goal I came to the start for, then it somehow feels natural that I don’t need to celebrate that separately. Maybe it’s a feeling that is a little difficult to put into words, but there is probably also some of that Estonian modesty in it.

And maybe I simply prefer to share my emotions with my family afterwards. To talk about exactly what happened, where something worked out, or what went well in the run. Those details mean more to me than celebrating at the finish.

So yeah, I’m probably not much of a celebrator on the hill. When things go well, I’m more likely to be quietly happy and move on towards new goals.

FIS - When I was doing research for this interview I came across Newschoolers posts from 2017 about you and your sister Kelly’s vlogs, hyping you guys up. This upcoming season will mark 10 years since that Newschoolers post, meaning you were just 9 or 10 when you were already on the freeski world’s radar. What's it been like spending more than half your life in the public eye as a freeskier?

HS - Actually, in a couple of years it will already be almost 20 years since the first vlog. At the time, consistently producing this kind of material on YouTube was still quite unique, and those videos had several purposes for my dad in the beginning.

Since we live in Estonia, skiing during the winter inevitably meant that we had to get out of Estonia. In the beginning, I think we only did one or two week-long ski trips to the Alps each year. But it had an immediate impact. Everything was so new to us – the big mountains, the good weather – and during those trips we were always on the mountain from morning until evening. But in order to start actually training more, and properly training on snow, we needed sponsors who could help make all of that possible.

Since freeskiing was still quite an unknown sport in Estonia at the time, it wasn’t easy to find sponsors there either. The vlogs became a way to introduce what we were doing outside of Estonia. Through them, the first bigger international sponsors found us quite quickly, and in that way the videos directly helped us slowly start living the life of skiers.

So with every year, we spent more and more time abroad during the winter. A couple of weeks became a month. At one point, my dad had to take unpaid leave from work so that we could spend longer periods training in the Alps. Eventually, he had to leave his job in Estonia altogether so that we could spend as much time on snow and train in the same conditions as everyone else.

But the other purpose, from the very beginning and still today, has simply been to have a video album. Through the vlogs, we could show our supporters back home, our family and grandparents where we were and what we were doing. In the first videos, I’m only one or two years old myself, so looking back now, it’s pretty cool to see where it all started and how much has changed over that time.

It’s actually quite interesting to think that my little brother is now taking his first steps on skis as well. In the future, he’ll also have the opportunity to look back through these same vlogs and see what his first steps were like and how our family spent time together doing sports.

I’ve actually never really been very conscious of the fact that I’ve essentially spent my whole life in the public eye. I haven’t attached any particular meaning or feeling to it. Rather, the videos have always just been a part of our own lives – what we do and where we go.

FIS - From that kind of hyped supergrom era to now, finally having your breakthrough season in 2025/26 and making good on all that promise and all that all that work, you've claimed your spot as one of the best in the world while becoming the FIS Freeski Park & Pipe Overall Crystal Globe winner. Can you tell me what it means to you to win that trophy?

To be honest, before the Silvaplana event I didn’t even know that I had a chance to win the Overall Globe. I was pretty sure it would go to someone who had performed well throughout the whole season in both slopestyle and big air. I couldn't have even dreamed about winning it this season.

After the slopestyle final, though, Birk Ruud told me that the next day’s halfpipe competition would decide whether he or I won the Overall Globe. Only when I got back to the hotel did I look at the standings and realise that I had a modest chance of winning it. I had to finish at least second in the halfpipe. Obviously, that added quite a bit of pressure, but I managed to do it.

What can I say about the Globe – it’s a nice globe and pretty heavy. Much heavier than I expected. When I picked it up with one hand on the podium, my first thought was, don’t drop it. But of course, the achievement itself was much bigger. It’s the first Overall Globe won for Estonia in FIS disciplines, so it definitely feels really good.

The emotion immediately after the win was definitely very strong, especially because there were a lot of Estonians there who had simply come to watch the competition and cheer us on. So when it became clear that I had a chance to take the Globe, it was an extra bonus for all of us.

And I think these bigger achievements are definitely things that will be nice to look back on years from now. Then you can remember everything you’ve done – and the same vlogs will definitely be helpful for that as well.

FIS - Let’s go through the highs of the season: you got your first World Cup podium at the Aspen Slopestyle; then an Olympic halfpipe silver finishing just .75 points back of gold; then Tignes slopestyle third place; and then double podium in Silvaplana - becoming just the second man to earn podiums in two competitions at the same World Cup stop after Gus Kenworthy did it over a decade ago. And then, of course, finishing it all off with the Overall Crystal Globe. Can you take me through each of those achievements and what you remember from those days?

HS - Aspen: Aspen was my first World Cup podium, and honestly, I didn’t expect to do that well there. From the very beginning, the first rail was sticky for me almost every run, and knowing that made it difficult to train. In training, we actually made a plan that if the rail is sticky, I would do an easier trick on it. That’s also what happened in the competition runs – it was sticky, and I did the easier trick we had agreed on.

Over the two runs, my best score was 75.90 points. It definitely wasn’t a score that would have made me expect a podium. I also started quite early, so waiting for the other riders in the finish area and then watching the scores with them was pretty tense. I was quite sure that every next rider would push me further down and eventually off the podium. But this time it worked out well for me. Definitely one of the most emotional competitions I’ve had.

Olympics: The slopestyle event at the Olympics went completely wrong. The plan worked quite well in training, but in qualification I made some proper mistakes on the rails, and I could forget about making the final. It was a complete disappointment. Looking back, we’ve thought that maybe we had made the plan on the rails too difficult. But what’s done is done.

After that, I was really looking forward to the halfpipe. We figured that if everything went right, then with a bit of luck, maybe something could happen. Compared to the halfpipe specialists, my biggest disadvantage is definitely my amplitude, but since the pipe was good and fast, maybe that difference didn’t show quite as much. It might also have been a surprise to the other riders that I did 16s on both walls, because I hadn’t competed in the halfpipe competitions very much alongside slopestyle. Over all the years, I had only competed in three World Cup halfpipe events before that.

But I was definitely happy with my halfpipe performance at the Olympics. As is typical for an Estonian, or for me, I didn’t really celebrate much there, of course, but inside I was definitely very grateful that the run had worked out.

Tignes: Tignes was especially nice because the whole family had come to cheer me on – my little brother and grandparents. Having family next to the course always gives me some extra energy. The competition was definitely important, but at least as important was skiing with my little brother and his first steps on snow. He hadn’t quite taken his first steps yet, he couldn’t walk, but he could already stand upright in his ski boots. So after training or competitions, I would always take him with me and we’d do a few easier runs together.

And of course, I’m also very happy with the third place in Tignes.

Silvaplana: Silvaplana is definitely one of my favourite places. Since the Estonian Ski Association doesn’t really support me, I have to put the budget together myself. So we can only do as many camps and training sessions as we can afford ourselves. My dad and I try to keep things fairly economical, stay in more modest accommodation and organise as much as possible ourselves.

In Silvaplana, though, there is an Estonian woman who owns a nice, cosy hotel – Albana. Whenever we are there, we are always welcome at her place, and at the end of the season it’s like an extra little boost. Great food, a spa and, of course, the chance to speak Estonian. It feels pretty much like being at home, even though we are in Switzerland.

As for the competition, Silvaplana was a real test of the nerves. For the first time, I managed to win the slopestyle qualification, which definitely raised expectations going into the final. My first final run didn’t quite work out – I came up short on the grab on the last jump. So on the second run, going last, I really had to pull myself together. The result was second place, and then I also got a fairly understated hint from Birk Ruud that the Overall Globe was in play.

The halfpipe final had quite strong winds and the pipe was slow, which immediately put me at a pretty significant disadvantage compared to the others. Somehow, though, I managed to put my run together there as well, and finished second again.

So, not bad – two second places in Silvaplana, the Overall Globe, and a very nice and quite unexpected way to finish the whole season.

FIS - Your Milano Cortina 2026 medal was especially significant for Estonia. Can you tell us the importance of winning Estonia's only medal at those Games, and the 11th OWG medal in your nation’s history?

HS - Looking back at that Winter Olympics and the medal I won there, for me it was first and foremost a very big personal achievement. I was the seventh Estonian athlete to win a medal for Estonia at the Winter Olympics, and in Estonia’s overall tally, it was our 11th Olympic medal from the Winter Olympics. I can of course be proud of that result.

It also felt very good to win that medal under the Estonian flag. How much or what kind of significance it has for Estonia as a whole is certainly difficult for me to assess myself.

There were a lot of people in Estonia watching on TV and cheering me on. When someone comes up to me on the street after the competition, or writes to me and says a few kind words, that they followed along and were happy for me, it definitely warms my heart. The medal itself is one thing, but knowing that your effort gave someone an emotion and brought them joy adds another dimension to the achievement.

Looking back, though, that medal may have had another, completely different impact. It was no longer just about my personal result, but also about the broader organisation and attitude towards sport in Estonia. After the medal was won, there was a reaction in Estonian sport, one result of which was the removal of the then-president of the Estonian Olympic Committee. So in a way, it may have been quite an important medal for Estonia.

FIS - Now that you have established yourself as regular podium threat in both pipe and slopestyle, what are your goals for the upcoming season? What are you most looking forward to in 2026/27, inside and outside of competition?

HS - This coming season, I’m definitely looking primarily towards the World Championships. Since the slopestyle event at the Olympics didn’t work out, I definitely want to get a good result there. Since I compete in three disciplines, I noticed that the competition schedules overlap at the World Championships, so we’ll see how it all plays out in the end.

I’m also definitely hoping to ski more together with my little brother this winter. Hopefully my mum, the rest of the family and friends will also find more time to join us for some competitions or camps. Being on the mountain together with family and friends has always been important to me, so it would be nice to do even more of that.

FIS - Awesome, thanks Henry. Can't wait to see what you've got in store for us in 2026/27!