Tadej Pogačar's final challenges: Milan-San Remo – the hardest Monument to win?

This is part of a mini series exploring five of the major achievements missing from Tadej Pogačar's already stunning palmarès: Milan-San Remo, Paris-Roubaix, the Vuelta a España, an Olympic title, and a record-equalling fifth Tour de France title. Can he tick these off? We're taking a closer look at each race to see how his chances look.

We don't need to tell you that Tadej Pogačar has won a lot of races in his career. Five Grand Tours, ten Monuments, two World Championships, countless other stage races and one-day Classics.

But, as an athlete's list of what they have achieved gets longer, attention often turns to the few things they haven't. And for Pogačar, despite his protestations that he isn't just trying to tick things off, there are some clear goals that would really allow him to 'complete' cycling.

As it stands, the most major of those are the two Monuments he's yet to win – Milan-San Remo and Paris-Roubaix – the one Grand Tour he hasn't won – the Vuelta a España – an Olympic gold medal, and a fifth Tour de France title to place him in the exclusive club of five-time winners.

Sceptics find all sorts of ways to discredit Pogačar, even suggesting that competition was higher during the 1970s than it is now in this richer, bigger, more advanced, more professional sport, but if he could tick off these last remaining challenges, it would be hard for anyone to argue his status as up there with Eddy Merckx in terms of achievements.

Whether he's going to focus fully on it or not, ticking off at least some of these wins is going to be a narrative that defines the rest of his career, starting as soon as 2026, so it's probably time to start thinking about how good a chance he actually has of achieving these last remaining challenges.

Today, the challenge we're going to look at is Milan-San Remo, the Italian Classic that is somehow both the easiest to finish and hardest Monument to win, and perhaps also the one that Pogačar has tried hardest to win without managing it yet.

Known for a long time as a sprinters' Classic, Milan-San Remo is almost entirely flat, save for a series of fast climbs in the finale. It's easy to finish, because the parcours really isn't that hard, but it's also hard to win, because so many riders can be there in the finale.

It does seem strange in some ways that we'd be considering a race that Mark Cavendish has won a goal for Pogačar, and Milan-San Remo has indeed been won in mass sprints before. However, it's a really versatile race that has also been won by solo climbers, small groups of Classics riders, demon descenders, and everything in between. So, as a rider who is good at pretty much everything, Pogačar should have no trouble winning it, right?

Well, yes and no. The problem for Pogačar is that Milan-San Remo is just not hard enough. It's not that he would have any trouble just accelerating on one of the final climbs, but the issue is that so many other riders can do that too, and he hasn't yet been able to do his signature move of just riding everyone off his wheel.

And unfortunately, the riders that can go with him can also outsprint him, as seen in this year's edition, where Pogačar did everything right, was in the winning group, but just couldn't outsprint Mathieu van der Poel.

We know that it hasn't worked so far, then, but can it work in the future for Pogačar? In many ways, I'd argue that there aren't a lot of things that the Slovenian and UAE Team Emirates-XRG haven't tried, and this year they threw a lot at making the race as hard as possible and leading him out so Pogačar could launch as hard as possible. So it's not that there is an 'easy' tactic to suggest for Pogačar to win.

How Pogačar could win Milan-San Remo

Ultimately, Pogačar really only has one way of winning: attack on the Cipressa, take no one with him, and solo to the line. The Poggio is too close to the finish; he'd struggle to build up enough of a gap, and none of the Tre Capi before that are really hard enough to launch an attack of any significance.

Could he go on the Passo del Turchino, more than 150km from the finish, and try to go for a truly epic solo win? I'm sure he's thought about it, but the chances of him pulling that off – no one really gets tired in Milan-San Remo until the end, so there's no fatigue to take advantage of – seem pretty slim, even for an alien rider like Pogačar.

So, Cipressa it is. Lead-out hard and fast, full-power attack, hold it to the line. Except, of course, he tried that this year, and it didn't work. That plan could be executed slightly better. For example, they could up the pace even earlier before the climb, and perhaps Pogačar's final lead-out could be a stronger rider, Isaac del Toro maybe, who in fact was meant to do that job this year, but couldn't, leaving Jhonatan Narváez double the work.

But it remains true that when the climb is 'only' the sweeping, flowing Cipressa, and it's the middle of Spring, there are a lot of Classics specialists who will have the might to follow Pogačar's acceleration, and he'll soon run out of climbing metres to try and drop them.

At the moment, Mathieu van der Poel has made it more than clear that he can follow that move from Pogačar, and on a good day, Wout van Aert can too. Mads Pedersen might not be far off the level, and each year, there are new riders who are going to have a go. As it stands, it seems like, as long as Pogačar lines up against Van der Poel at Milan-San Remo, there's no way for him to win it. Case closed.

Except, it really isn't that simple. A lot of commentators will try to tell you it is, and that Van der Poel will always beat Pogačar in this race, and that's that. And whilst Mathieu van der Poel isn't slowing down any time soon, there does seem to be a pretty obvious scenario we're overlooking: what if Van der Poel, or Filippo Ganna, or Van Aert aren't there one year?

It seems to be taking as a given that the same riders will be contesting Pogačar at Milan-San Remo until the end of his career, but we're really just one injury, sickness or change of plans away from Van der Poel skipping the race, and then the door opening up for Pogačar's plan to actually work. I'm not saying it would be automatic, and of course, there are more riders who would challenge Pogačar, but if we're arguing that he could win without just a couple of riders, it seems silly to dismiss the idea that they might just not be there one day.

Of course, the problem is that this all relies on external factors, and it's not really a tactic or strategy Pogačar can rely on. It might never happen before he retires. But equally, it's not inconceivable, and it feels like a very fine margin between Pogačar taking podium after podium, or turning that into a win because one rider has to skip the race. There are so few riders who can beat him in Milan-San Remo that it would be very easy for this scenario to happen.

So, my verdict? Well, I think Pogačar's chances at winning Milan-San Remo are essentially going to come down to luck and fate. He's already proven that, against the current competition, even his best-laid plan and only realistic strategy aren't quite enough to drop a rider like Van der Poel. More than anything else going right for Pogačar, he needs something to go wrong for someone else – or for them to just focus on a different goal – but then he could.

This will undoubtedly be a source of frustration for Pogačar and his fans, knowing he is so close to ticking off Monument number four, but there may also be some solace in knowing there really isn't much more he could do. Pogačar just needs to let fate decide this one.

But if the way fate has treated him so far is anything to go on, I wouldn't bet against seeing the Slovenian win on Via Roma one day. Things do tend to fall his way eventually.

What do you think? Can Pogačar win Milan-San Remo, or could it end up something he's left chasing? Tell us your thoughts in the comments!