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It was sometime near the 240th kilometer of the 2014 Milan-San Remo when Luca Paolini’s hands were so brittle and frozen that the Katusha team car had to heat up water in an electric kettle, bottle it in the car, and get it to Paolini, so he could dump it on his useless digits to shock enough feeling into them so he could finish the last 60 kilometers of the run into San Remo. Up ahead of him in the breakaway, Mark de Maar had to stick unwrapped energy bars in his pants to thaw them to chewing temperature. The year before, the race had to be moved over a mountain pass because snow was piling up and making it impossible to bike through (as you can see above).

At 290.1 kilometers, tomorrow’s Milan-San Remo is the longest race in cycling. The first Monument of the year is a race of survival, as much an exercise in managing physical deterioration over seven hours than boldly striking out and grinding your foes down. While Grand Tour mountain stages have been compressed to include the highest density of steep climbs in the shortest stage possible, MSR stands as a foreboding throwback.

The race’s profile isn’t particularly threatening. There’s just that one long, slow climb in the middle that nobody’s going to escape on, and a handful of punchy little climbs towards the end. The Cipressa is only a Cat. 4 climb, but the 260+ kilometers it takes to get there will turn legs into oatmeal and make pros feel like weekend doofuses out there. Its friend the Poggio is even less pitchy, but it summits out 5.4 kilometers away from the finish, much of which is a tortuous descent down into the city. That little distance is tempting enough to inspire whichever escapees still have legs to take a flyer, but long enough for a well-drilled team to reel a soloist in.

Sometimes, a rider will make it to the finish after taking off on one of the finishing climbs. Sometimes, the whole bunch makes it to San Remo together. occasionally, you’ll get a small break of riders contesting a sprint. The structure of the lead group that makes it intact to the finish is pretty unpredictable year-to-year, and of all the monuments, this one has the widest breadth of contenders. Grand Tour bros like Vincenzo Nibali think they can win, as do pure sprinters like Mark Cavendish. The winner is usually a sprinter or a hearty classics ox like Fabian Cancellara or Alexander Kristoff, but the race is weird and long enough that a climber like Nibali could legitimately win one of these years.

The race’s geographic width recalls a now-dead era of cycling when the sport was primarily an odyssey of endurance. Early Tours de France would have stages in excess of 400 kilometers. Old one day races like Paris-Bourdeaux would take all day and span the entirety of France. That brand of racing doesn’t make for compelling television or racing really, so it’s been phased out in favor of shorter, punchier races that keep stars healthier.


Milan-San Remo is an anachronism of that era. 290 kilometers is long enough that nobody can really clamp down and control the race. When the race does end in a sprint (usually the most boring outcome), it doesn’t look anything like hyper-tuned up sprint trains you’d see in the Tour. The last two editions of the race have ended with a medium-sized group contending a sprint, and they’ve both been brutal, dragged-out gallops to the line. John Degenkolb’s 2015 victory was as clean a sprint as you’ll ever see in this race, and even then, it was still a fairly futile finish.

Unfortunately, goddamn global warming won again, the weather will be nice tomorrow, and the race will not be an Arctic rainfight. Kristoff, Peter Sagan, or bad jewelry enthusiast Michael Matthews will probably win, but not before Nibali takes his now-annual failed attempt to ride away on the descent off the Cipressa. The winner tomorrow won’t have to trek uphill both ways through a snowstorm like Gerard Ciolek in 2013 and Alexander Kristoff in 2014, but he’ll still have to traverse from Lake Como all the way to the Mediterranean Sea.