Philippe Gilbert and his final shot at Milano-Sanremo and monument sweep

Philippe Gilbert isn’t quite yet Don Quixote chasing windmills, but he could be getting close.

As the most recent rider on the cusp of winning all five of cycling’s monuments, the veteran Belgian star could be running out of gas and out of chances to become only the fourth rider to join one of cycling’s most elite clubs.

Could the wind finally be at his back in what might be his final tilt at the Milano-Sanremo windmill? Gilbert was cautiously optimistic when VeloNews‘ James Startt caught up with last week at Paris-Nice.

“I am happy with my form right now because I am coming back from far,” said Gilbert, on his recovery from a knee injury suffered in a crash in the opening stage of the 2020 Tour de France. “It was a special season for everyone [last year], but for me, it was very special with the crash. We will see when I will be at my best. It’s not now, but it’s coming.”

Also read: Philippe Gilbert impressed by Wout van Aert, Mathieu van der Poel

Gilbert has raced Milano-Sanremo some 16 times since his debut in 2004 and only missed one edition, in 2016. He hit the podium with third in 2008 and 2011, and finished three more times in the top-10, including ninth in 2020.

There are three ways to win cycling’s classicissima — a sprint, an attack over the Poggio, or something earlier. Let’s look at his best chances:

Long-distance raid: No rider since Gabriele Colombo in 1996 has won the race beyond the Poggio/sprint scenario. Colombo was the last rider to successfully attack over the Cipressa climb at 22km to go to the finish on Via Roma. Despite the race’s long-distance — at 299km it’s the longest race in 2021 — the race is almost never won in a long-distance attack. The last old-school victory came in 1991 when Claudio Chiappucci attacked out of a group along the capi on the coast road.

Will Gilbert try to out-fox the peloton, and try something on the Cipressa or perhaps before the Poggio? Highly unlikely. There are too many teams and too many riders hitting the Poggio these days for anything early to have a realistic chance to make it to the line.

Our hunch: No early go for Gilbert on Saturday.

Sprint on the Via Roma: Back in his prime, Gilbert could win the occasional bunch sprint out of reduced groups. The mass gallop down Sanremo’s Via Roma, however, simply boasts too much horsepower for Gilbert to have a chance. Milano-Sanremo isn’t called the sprinter’s classic without reason, and there’s a long list of favorites Saturday with a very fast finishing kick.

So what are Gilbert’s chances in a bunch sprint out of an elite group of 40 top riders? Not good. Sam Bennett and Davide Ballerini (Deceuninck-Quick-Step), 2016 winner Arnaud Démare (Groupama-FDJ), teammate Caleb Ewan, Fernando Gaviria and Matteo Trentin (UAE-Emirates) and Michael Matthews (Team BikeExchange) are among a handful of sprinters who could relegate Gilbert to also-ran status Saturday.

Our guess: An elite kick down the Via Roma won’t see Gilbert win the monuments club.

Attack over the Poggio: Gilbert’s best chance to join Eddy Merckx, Rik Van Looy, and Roger De Vlaeminck is to attack over the Poggio. Topping out at 5.4km to go, the big-ring climb is the launching pad for late-race attacks to fend off the sprinters. Pure power riders like Fabian Cancellara or Wout van Aert can churn the watts to gap the group. Simon Gerrans won in 2012 by hitching a ride to Spartacus, and after taking a few choice pulls to help stave off the pack, he pipped Cancellara and Vincenzo Nibali at the line.

The Milano-Sanremo puzzle is always a tough one to crack. And the problem for Gilbert is that there is another baker’s dozen of riders in the bunch thinking that the Poggio also presents their best chance. Gilbert will need to have his absolute best legs in order to follow the likes of Mathieu van der Poel and Julian Alaphilippe over the top, and then time his sprint to perfection to beat anyone who makes cycling’s most elite selection.

All the elements will have to come together Saturday. Gilbert will have to positioned perfectly up the Poggio, have the legs to follow accelerations from any one of the peloton’s mega-fauna, and then have the after-burners to win out of a three-up sprint.

At 38, time is running out for Gilbert. This could be his best and final tilt at the elusive Milano-Sanremo windmill. If the stars align, magic could happen Saturday down the Via Roma.

If he falls short, Gilbert will still be in very good company. Sean Kelly, Fred De Bruyne, Louison Bobet, Germain Derycke, and Hennie Kuiper are also in the “four-win” monuments club.

What’s obvious is that he has absolutely nothing to lose.

Our prediction: Gilbert won’t have the legs to follow today’s holy trinity of van der Poel, van Aert and Alaphilippe, and will finish near the front of the chasing group.