On Friday, however, the 19-year-old wowed the judges with a thrilling halfpipe run to earn a surprise silver. It is the only medal Estonia have claimed at the Milano Cortina Games.
Prior to the Olympics, Sildaru had never reached the medal podium in any World Cup halfpipe event. His highest halfpipe ranking was a sixth-place finish in 2025.
While Sildaru may not have been making headlines, halfpipe bronze medallist Brendan Mackay of Canada said he was aware the Estonian teenager was a threat.
"I knew he was a dark horse the whole time," Mackay said after the halfpipe contest in the Alpine town of Livigno. "He has all the tricks. His run is so technical, he grabs so well."
Most freestyle skiers specialise in halfpipe alone or in slopestyle and big air, but not all three. China's Eileen Gu is the sole female freeskier who tackles the three disciplines. Doing all three means less time to practice each one.
Sildaru said he chose to compete in all three simply because he enjoys them.
Winning the silver medal "definitely means a lot," he said, particularly given his disappointing results in the other two disciplines.
He started the contest by falling on the first of three trips down the halfpipe. On the second run, Sildaru was near flawless, spinning and twisting through the air and earning a score of 92.75 that propelled him to the top of the leaderboard.
He improved to 93 on his third run but was overtaken by American veteran Alex Ferreira's 93.75.
Sildaru said he did not envision he would hang on to the first-place position.
"I knew there were some big hitters still coming, so I was sure I was going to be beaten," he said.
Ferreira, the gold medallist, admitted he did not expect to see Sildaru standing next to him at the victory ceremony.
"Did I think he was going to be on the podium today? Just frankly no," Ferreira said as he sat next to Sildaru at a post-event press conference. "But I am insanely shocked and just so, so happy for you. Unbelievable performance."
Sildaru's sister, Kelly Sildaru, won bronze in slopestyle at Beijing 2022. At Milano Cortina, she finished 13th in the halfpipe qualification round and failed to make the finals.
