Tadej Pogačar and Mathieu van der Poel (and their plus-one) put on a helluva show yesterday at Milano-Sanremo, which is all well and good, because we need a show at the end of Cycling’s longest day. But what was really on display was their respective legacies, the sport’s two most important active portfolios, and there this race had a lot to say.

First, can we all agree to leave Strade Bianche out of the discussion? Probably not, but I am adamant about this. The Old-Heads have always said that the season starts at MSR, and as a newly-certified member of that club, I agree. If your earliest political memories involve Richard Nixon, chances are you have considered not sweating the small stuff. And that is ultimately what every race is before the Earth’s position announces the official start of spring (give or take a few days). La Primavera is where you know you are seeing the protagonists with their full powers available to them. I bring this up mostly to say how liberating it is to not operate a website where, by site manager rules, I should be thinking of stuff to say in February.

Van der Poel scored his second win in three years, sandwiched around gifting a sprint victory to his teammate Jasper Philipsen, making it three Alpecin wins in a row. The win came at Pogačar’s expense, and made me wonder if Pogačar can win this most unique race. Monuments being Monuments, this is a huge question. Van der Poel is the main obstacle, arguably even his superior, though the counterargument is age, but still:

Pogacar: 7 Monuments; 1 Flanders, 2 Liege, 4 Lombardia

Van der Poel: 7 Monuments; 3 Flanders, 2 Paris-Roubaix; 2 Milano Sanremo

The case for van der Poel is that he has three places to win and win often. One of those — de Ronde — overlaps with Pogačar’s skillset, and we will have much to say about that in a couple weeks. Van der Poel has no chance to win all five and only the slimmest hope of contending at Liege (with a mellower course? I dunno). Pogačar could run the table. I really don’t like his chances in Paris-Roubaix, but I could see it. I do like his chances in La Primavera, but after this weekend, I don’t love them.

Mostly this post is about the Slovenian, so let’s get this out of the way and say that van der Poel is perfectly suited for MSR. He could be in control of the race for a while, with good fortune and especially with Pogačar around to shift the power from the sprinters. Merckx holds the record for wins, a whopping 7, so at age 30 he is one wrong move away from having no chance at the record. But he could well be in the second tier. Three more wins elevates him past Zabel and Bartali (4 wins), behind only Merckx and Costante Girardegno (6 wins), if we are going all the way back (which obviously we are).

For Pogačar to win, he has to not only beat van der Poel but a few other guys you could see stopping him. He has to remain super aggressive and not let the sprinters remain in contention after the Poggio. He alone can actually to the seemingly impossible — narrow the number of possible winners, in this famously wide-open race. If he doesn’t, his chances of winning the bunch sprint are infinitesimal. [Autocorrect insists that word has only one “s”, because it hates Italy. The feeling is mutual.] Let’s look at his other pathways to a win.

The Solo Escape

This is Pogi’s signature, but going back to my point about winter… this isn’t Tuscany two weeks ago. The leg warmers are off, and more importantly, the ramps to escape are few. Because of that, the power-climbers know when to be on their guard: anywhere inside 80k, but especially starting at the Cipressa. With their full prep at Tirreno or Paris-Nice behind them that is not too difficult a task. I rate his chances 1/25 in ever being able to do this.

The Not-So-Solo Escape

This is the likely outcome for Pogi, where he drags a couple guys to the line and outduels them. There are two different versions of this.

-The 2023 Plan

If I am misremembering that year, or 2024, then just call it the Poggio Plan. That is where… do you even need me to type it? No, you do not. It can work but it would require him to have a little more than he normally does in his legs, and he will attract even more attention than the next option would, so I don’t think it is much more than a slim pathway to a win. The problem for him is that one little extra MSR wrinkle, the Poggio descent. Many an edition has been won by ace descenders, most recently his countryman Matej Mohorič, but not all Slovenians descend the same. And since Tom Pidcock is his junior, Pogačar won’t often be able to discount the chance of Pidders catching or passing him on the way down. Can he get 10 seconds over Pidcock at the summit? Does he need more like 15 or 20? That’s a lot for a power climb like the Poggio.

He can win this way, of course. A reduced sprint is worth a shot given his ability. But the guys who can stay with him can sprint too. I give this a 1/5 chance of him eventually winning this way.

-The 2025 Plan

Yesterday was Pogačar’s ideal plan, let’s call it the Cipressa Combo, and he executed it beautifully. If the Poggio plan gives him one chance to get away, the Cipressa Combo relies on enhancing the Poggio Plan by eliminating 98% of the race ahead of time and softening up the rest. Van der Poel was on the edge several times, and if you rerun this identical race 10 times, Pogačar probably cracks vdP at least three of them.

That’s not a high percentage though, so over time Pogačar will have to hope that he can soften up the legs of van der Poel and the rest a bit more. Maybe some different wind conditions, or maybe RCS monkeys around with the course, as they have in the past. Maybe he doesn’t get away from them but wins the sprint, either with better tactics or because the other guys have less in the tank. As noted above, I’ll call this a 1/3 chance. Maybe higher if you factor in injury or illness befalling vdP or the others, though that cuts both ways.

Last Hope: Bide Your Time

However discouraged Pogačar may feel by yesterday, and it’s not often he sounds like there was nothing he could do, the reality is that he is nearly four race-years younger than the Dutchman (vdP born in January, Pogi September). In 2030, will we still like van der Poel’s chances of winning the way he just did? In 2031? Because we will still like Pogi’s. Who knows what other riders will insert themselves into the conversation by then, but if Pogi hasn’t won MSR yet, you can guarantee right now that his 2031 race preparation will be built around correcting that aberration.

I am leaning toward him getting one win here. Of course, I thought for sure Tom Boonen would get one, and that never happened, but Pogačar can control races like no other, not even Boonen and prime Quick Step in the classics. Moreover, I really think he was seconds away from winning yesterday, lower down on the Poggio, although van der Poel’s counterattack at the top says otherwise (and pretty much announced his victory). This was a two-man high wire act, with a third man who I should actually mention by name — Filippo Ganna — waiting to pounce if they weren’t careful. It was uplifting to van der Poel’s fans who might have entered the season discouraged about anyone slowing down the new World Champion. And it is a bucket of cold water on Pogi, at least for two weeks, when… well, let’s talk about that later.