The Rusted Guns of Milan-San Remo

Three hours of boredom followed by seven seconds of sheer terror

Photo Credit: Pauline Balliet, ASO

I love a passive intake sport. One that you can check in with periodically while you’re doing laundry or filling out a spreadsheet, or even sleeping. I hate golf but I love a Sunday afternoon nap on the couch with golf on the TV. Last Friday night I slept badly, but I dozed off during the last 15 laps of Saturday' morning’s Formula 1 race—all of 20 to 25 minutes—and woke up feeling like a new man.

Cycling is a great passive intake sport. When the race is sedate, it’s just a progression of pretty colors on the TV, with calming but forgettable narration. I don’t know if this is true in the rest of the world, but in the U.S. and U.K. (or wherever FloBikes gets its feed from), I think there’s some obscure statute that makes it illegal for cycling commentators to have a grating speaking voice. It’s very calming. Some of my formative early cycling-watching memories involved nursing a hangover in my early 20s while the Phil Liggett and Paul Sherwen¹ talked me through the Tour de France on NBC Sports Newtork.²

All of which is to say that you don’t need to worry about setting an alarm for Milan-San Remo on Saturday. The first monument of the season is the most predictable. It’s six of the most boring hours anywhere in the sporting calendar, followed by about 10 of the most thrilling minutes in cycling.

One of the first-post, Day 1 lessons I wanted to put forward in this newsletter, a fundamental truth that makes it possible to understand the sport, is this: Over flat ground, with no obstacles in the way, the peloton will finish together. The shape of a race—which riders have a shot at winning, and how they ride the race tactically—is determined by the shape of the obstacles.

At Milan-San Remo, there are three obstacles worth mentioning. The first is the Passo del Turchino, which comes at the end of about 25 kilometers of constant low-grade uphill pedaling. The final kick is 2.5 kilometers at 5.8 percent and tops out at 549 meters, which is pretty high considering most of the race is run at or near sea level.

But it doesn’t split the peloton for two reasons: First, it’s so gradual any pro can get over it easily, and it comes less than halfway through a race that’s the best part of 300 kilometers. So when riders to attack on the Turchino, it’s always a doomed breakaway launched for the purpose of getting TV exposure. There’s about 130 kilometers of nothing, then the hardest parts of the Turchino, and then another 130 kilometers of nothing.

And then the shit hits the fan. With 28 kilometers to go, the peloton hits the Cipressa, which is 5.6 kilometers at 4.1 percent. It’s not nothing. On a hilly classics course—even a Flemish cobbled race with nothing but speed bumps and old shell craters to vary the terrain—a climb like that can break up the peloton. But after the Cipressa, there’s another 10 kilometers of flat road. And because the peloton’s been hanging out on the world’s longest group ride all day, every team with an interest in winning the race is well rested and can chase down any attack. It’s been 28 years since an attack on the Cipressa stayed away until the finish.

Which means the race is always³ decided on the last climb, the Poggio: 3.6 kilometers at 3.7 percent gradient. The shallow incline and short duration makes it accessible to big, beefy riders like Mathieu van der Poel and Filippo Ganna, who can hold the wheel of elite puncheurs by grinding out maximum power. They only have to do it for about three and a half minutes at full speed.

But the roads both up and down the hill are narrow and winding, lined with unforgiving curbs and jagged stone walls. There’s no room for the peloton to spread out or for a counterattack to be launched, and even if there were, the pace on this climb is absolutely hellacious.

If you’re not in the first dozen riders at the foot of the Poggio, you’re toast. If you freewheel and try to get someone else to come through and pull, you’re toast. If you chicken out going around a corner and use too much brake, you’re toast. In a calendar of slow-burn action and gut-wrenching anticipation, this is 10 minutes of sudden death overtime.

In the past 10 or 15 years, the race has always been won on or after the Poggio, but it’s happened in a variety of ways. We’ve had an opportunistic attack succeed because of mere moments of indecision in a chasing peloton, as with Jasper Stuyven and Søren Kragh Andersen’s jaunt off the front at the Via Roma in 2021, or Vincenzo Nibali’s solo victory in 2018. The 2022 winner, Matej Mohorič, benefited from the favorites playing chicken behind him as he screamed down the backside of the Poggio. It remains one of the most thrilling rides in recent cycling history.

And every so often you get a bunch sprint. The true sprinters struggle even on this relatively modest climb, but if the puncheurs and classics specialists dick around, they’ll come back and dust everyone on the long, wide finishing straight.

There are Milan-San Remo winners still active today—none of them have won it more than once—and seven of them are on Saturday’s start list. But a few of them have passed the point in their careers when they’d be considered favorites, and one or two others would need the race to come down to a bunch sprint. At the risk of tempting the wrath of the predictions genie, I’d be stunned if that happened.

See, for a monument, this isn’t a particularly strong field. Wout van Aert is staying home; Visma-Lease a Bike is throwing its weight behind Christophe Laporte but not bringing as strong a squad as it did to Omloop Het Nieuwsblad and Kuurne-Brussels-Kuurne. I’d be mildly surprised if Arnaud de Lie didn’t win this race eventually, but it won’t be this year; he’s still not right after a crash at Le Samyn a couple weeks ago. Soudal-Quick Step is consolidating its efforts behind Julian Alaphilippe; Tim Merlier—another sprinter, but one in pretty good form at the moment—is going to watch on TV.

So who has a shot to win?

Mohorič could do what he did in 2022: Make it over the Poggio with the favorites and build the winning gap with a sphincter-puckering, live-fast-and-die-young descent. So could Tom Pidcock. Ganna is a fascinating case; he’s got a monument win in him, and he finished second last year, outsprinting van Aert of all people at the line. I don’t know if he’s explosive enough to create a gap, but he could absolutely sustain one, or pull back a solo attacker on the final descent. Alberto Bettiol just won Milan-Torino with a long solo effort, but as much as I’d love to see him do the same here, I just don’t see a credible path to victory.

If it comes down to a bunch sprint, you’d have to favor Jasper Philipsen, especially if Alpecin-Deceuninck can keep its team near the front of the race after launching van der Poel up the Poggio. A smaller, faster leading group would probably drop Philipsen, but not a number of other fast finishers: Biniam Girmay, Laporte, and the Lidl-Trek duo of Mads Pedersen and Jonathan Milan.

Milan in particular interests me, and not just because I checked and no rider has ever won a monument with which he shares a name. He’s looking for that breakthrough signature win, and even though he’s the size of a motor home, the Poggio is short and shallow enough that I could see him just brute force-ing his way over and staying with a leading group of 20 or so riders all the way to the end. He’s fast enough to win a sprint with anyone in this race, but he’s not so accomplished that the other teams are going to be desperate to drop him.

It’s also worth mentioning that a couple of the Lidl-Trek support riders, like Alex Kirsch and Toms Skujiņš, have ridden their asses off so far this season. If Milan or Pederson or both makes it over the Poggio with or close to the leaders, with teammates in his group, Lidl-Trek could run down a solo escapee.

With all that said, I would be staggered if anyone other than van der Poel or Tadej Pogačar won this race. Pogačar has already won three of the four monuments he’s reasonably capable of contending for⁴ and he wants this one so bad you can smell it through the TV.

Pogačar has ridden this race three times before. In 2020, he was 12th, in the second finishing group behind two escapees. In 2022, he was fifth, in the second finishing group behind a lone escapee. And in 2023, he was fourth, in the second finishing group behind a lone escapee.

There’s not a ton UAE Team Emirates can do to help Pogačar. They were originally going to bring Brandon McNulty, but he scratched after his third-place finish in Paris-Nice, and has been replaced by Our Man Isaac Del Toro. Assuming UAE can bring Pog to the foot of the Poggio in one piece and near the front of the race, the only thing they can do is what they did last year: Put Tim Wellens on the front and have him floor it until he collapses, in order to break up the group. Wellens is back in the squad this year.

In addition to being one of the top stage racers and climbers in the world, Pogačar is also a top puncheur, and he needs to accelerate early and get some distance between himself and van der Poel before they come over the top of the final climb. If he can’t, van der Poel will either counterattack and ride away—as he did last year—or beat Pogačar in a heads-up sprint. These two will create the winning move, and it’s likely that one of them finishes it off.

Predictable? Maybe. But seeing it unfold is thrilling nonetheless.

1. RIP to a legend

2. RIP to a legend

3. For practical purposes. I guess it’s theoretically possible someone could attack earlier.

4. I guess we can’t completely write off a Paris-Roubaix challenge someday, but if he pulls that off he’ll have basically solved the entire sport and I’ll probably just get out of show business.