
Vincenzo Nibali built a legacy across his career as a fearless attacker and an excellent general classification rider. The "Shark of Messina" managed to break Team Sky's Tour de France reign during the last decade, won all three Grand Tours to join a prestigious club of only seven cyclists to have achieved this feat (for now), won both Italian Monuments, and wrapped up his career while still at the top.
That's why it's rather a surprise to learn that for the Sicilian, winning his final, fourth Grand Tour back in 2016 may have been the hardest task of his career.
"I was incredibly stressed," Nibali admitted in an interview for Gazzetta dello Sport. "But even 15-20 days before the start, that was how it was that year… I both loved and hated the Giro. I loved it because it's the Giro; I'd grown up dreaming of that race, like everyone else. I hated it because it felt like I had to win; I raced under the burden of having to come in first. I felt like people expected a lot from me. Everyone."
The public was not always quite aware. But the Italian rider was hardly at his best for the 2016 Giro d'Italia. "It's never been emphasized much, but during the Giro d'Italia, I always suffered from allergies, and that held me back a bit. My eyes would burn, I'd start to breathe worse, and I'd feel bloated. Then I'd take tests, and they'd tell me: 'Nothing's wrong, you're a false allergy sufferer.' Yet I felt bad, except in a few places: in the mountains, for example, I felt better. But I never complained too much."
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Never give up
Even though Nibali had already won the Giro in 2013, the 2016 edition was not going well since the beginning, especially in the mountain time trial up Alpe de Siusi, where Nibali lost two minutes to Steven Kruijswijk - and seemingly the entire race as well. And then when Kruijswijk took another minute and a half the following day, Nibali was down for counting.
"I was fighting, but mentally I wasn't free. I was suffering. I attacked at Asolo, and I remember arguing a bit with Valverde. It wasn't like now, when everyone seems like friends; we were really fighting during the race."

Vincenzo Nibali was a specialist for brutal mountain stages
But just three days later, the race was thrown upside down with a queen stage over Colle d'Agnello. The hellish conditions saw Kruijswijk make a mistake in descent and lose over four minutes, suddenly bringing Nibali's chances back alive as new leader Esteban Chaves held less than a minute advantage with a final big mountain day to come. "It was a relief. I didn't think I'd win the Giro, not even then. I only realized later, after the press conference, that victory was within my reach."
The key to his comeback, as Nibali outlines, was to never lose sight of his goal, even if the situation wasn't going to play out in his favor. "You don't abandon a race halfway; something can always change; look what happened on the Finestre last year," Nibali recalls Simon Yates' iconic ride from the 2025 Giro.
Could there have been a fifth?
His wins aside, Nibali does regret not winning another Grand Tour, in particular the 2010 and 2019 Giro d'Italia. Back in 2010, the Italian had to give up leadership in favor of a more experienced teammate, Ivan Basso, while in 2019, he and Primoz Roglic underestimated Richard Carapaz.
"I don't want to take anything away from Basso, but without that crash on the dirt roads, it would probably have been the 2010 Giro: I would have kept the pink jersey, and it would have been a different race. And maybe the 2019 Giro, when Roglic and I went to war and instead we both lost it."
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Ondrej ZhasilCycling Journalist
Ondřej Zhasil is a cycling journalist at CyclingUpToDate and has been part of the team since 2023. He is based in Ostrava, the third-largest city in the Czech Republic, and covers professional cycling across the main UCI competitions, including the Tour de France, the Giro d’Italia, and La Vuelta a España. A key focus of his work is startlist analysis and pre-race coverage, where he examines team selections, rider line-ups, and tactical scenarios ahead of major events.
Alongside WorldTour coverage, Ondřej has developed specific expertise in junior cycling and in racing across East Asia, including competitions in China and Japan. He also maintains a broad working knowledge of other disciplines and levels, including cyclocross, while continuing to expand his understanding of mountain bike racing.
Ondřej holds a bachelor’s degree in Mathematics and Physics, which supports his analytical, data-driven approach to performance and race analysis. In his reporting, he regularly uses ProCyclingStats for results, statistics, and historical context. He places strong emphasis on careful sourcing, editorial accuracy, and updating articles promptly when new, verified information becomes available.
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- 18 broken bones. 78 crashes, among 30 rider per year is a lot. so for a rider over 15 seasons, they will break their bones 7-8 times and crash 38 times.abstractengineer04-11-2026
- i dont think he is ready ot win against the top 2 or the 2nd rung of evenepoel, del toro , Almeida. In the third week in the TDF he was very very defensive, no attacks. i think he was exhausted. right now he needs time not the brutal Giro or the intense TDF.abstractengineer04-11-2026
- Rota is an excellent rider to get in a break with because he always does his turnchapmanesque04-11-2026
- That 3000 extra that the Tour de France is built up in the flat stages
Rafionain-Glas04-11-2026 - maybe this is something else they can protest in the streets of France.mij04-11-2026
- his Roubaix win was amazing. not to take anything away from him - arguably one of MVDP's wins was at the expense of a WVA flat - but so many things need to line up to get one of these. He had a perfect race with fewer bike issues on an attritional course. And crazy strong as usual. Glad he got this done.mij04-11-2026
- Orts was a super smart signing with the new rules regarding cross and UCI pointsmij04-11-2026
- yeah... you're right...PogiSloFans04-11-2026
- Podcast sounds great. Two so called experts stating the f*cking obvious.wrsty04-11-2026
- A mindset that reminds me of Tim Declerq. I loved watching that guy just pound away the kilometers, hours at the front, holding an entire breakaway in check on his own. Bjerg seems like a similar guy. Curling, the team sport.RidesHills04-11-2026
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