This tactic is the only hope for Pogačar to win Milan-San Remo

Tadej Pogačar might be getting predictable, but he’s never boring.

And Saturday’s Milan-San Remo will, predictably, see the Slovenian superstar try to blow up the race and finally win the lone monument hard-wired against his explosive style of racing.

King Pog will line up in Pavia (not Milan), determined to crack the monument that continues to defy him. And if he’s going to do it, the winning move almost certainly must come earlier than the typical MSR playbook.

We all know what he is going to do. The question is, can anyone stay with him?

La Classicissima has followed the same script for decades.

The peloton barrels down the Ligurian coast for nearly 300km before the race explodes on the Poggio, the short, punchy climb just 5.5km from the finish. The survivors plunge toward San Remo. A reduced group sprints for glory on Via Roma.

It’s a blueprint for cycling’s most unpredictable finale that’s crowned a motley crew of sprinters, punchy classics specialists, and opportunists.

And that’s the exact scenario Pogačar cannot win.

On Saturday, he will try to hit the repeat button on his true best chance: an attack on the Cipressa.

Breaking San Remo before the Poggio

By professional racing standards, the Cipressa hardly rates as a climb. In today’s turbo-charged peloton, it’s a big-ring speed bump.

And for decades, since Gabriele Colombo attacked there to win in 1996, the climb has served mostly as a jostling for position before the real throwdown up and over the Poggio.

Last year, Pogačar defied convention — like he’s been doing all decade long — and uncorked a searing attack on the Cipressa that dynamited the race.

It was the kind of trademark, logic-defying move from Pogi that no one had dared in modern San Remo racing. Historically, attacks from that far out never succeed. The distance to the finish is too long, the terrain too fast, and the collective interests of the pack too strong.

Unfortunately for Pogačar, Mathieu van der Poel and Filippo Ganna had the legs to hitch a ride.

The trio worked together to fend off the bunch and set up a historic raid, but Van der Poel had the jet fuel to blunt Pogačar’s punch. Van der Poel ultimately won his second MSR, while Pogačar finished third.

Also read: How to Watch Milan-San Remo 2026 in the USA, Canada, and Worldwide

Now Pogačar is stuck in a trap. Not that he cannot win from a reduced bunch sprint, but he knows if he waits for the Poggio, his chances melt faster than ice in a spritz if riders like Jasper Philipsen or Paul Magnier are still hanging on.

That’s why he tried something different last year.

And that’s why he has no choice but to try again.

A new ally: Isaac del Toro

This year, Pogačar will count even more on UAE sidekick Isaac del Toro.

The Mexican star is hot off victories at the UAE Tour and Tirreno-Adriatico and could be a key ally. UAE Emirates-XRG’s Jonathan Narváez and Tim Wellens, two riders who helped set him up last year, will not race due to injuries.

Del Toro’s job will be simple: detonate the race before Pogačar uncorks his attack.

This year, the advantage of surprise will be gone. The entire peloton will be bracing and waiting for the Cipressa.

And 2026 could be his best chance to knock down La Primavera, and leave Paris-Roubaix as the last target to complete the elusive monument sweep.

Pogačar will want to take full advantage this weekend in his sixth crack at MSR against a bruised and battered peloton.

This year’s injury list runs deep. Longtime favorites Mads Pedersen, Michael Matthews, Neilson Powless, and Olav Kooij are all MIA, while others arrive at MSR after a spring campaign marked by crashes, illness, and chaos.

Van der Poel looks like he’s on another planet — we’ll find out Saturday.

Forecasters are calling for crisp spring racing conditions, with onshore cross-head winds that could make the run from the Cipressa to Via Roma even harder to pull off. We might see an all-in Hail Mary on the Poggio, but that’s not worked in the past.

A few riders have surprised with closing-kilometer solo raids at the end of the race, like Fabian Cancellara in 2008 or Vincenzo Nibali in 2018, but that might be even harder for Pogačar to try if Van der Poel is glued to his wheel.

Thankfully, organizers have resisted pressure to alter the course.

That’s why San Remo is so intriguing for Pogačar and so fascinating to watch him try to decipher the winning code.

MSR is the rare anti-Pog race.

This year or bust

Last year proved that even Pogačar’s most violent acceleration is not enough if the wrong riders follow.

If Van der Poel or Ganna are still on his wheel over the Cipressa and onto the Poggio, the odds quickly tilt against him.

That means the equation this weekend remains brutally simple.

To win San Remo and check it off his monument list, Pogačar must do something the race rarely sees — he must drop everyone.

The Cipressa offers the best chance to make that happen.

The longest monument is often called the easiest to finish, but the hardest to win.

And that’s proving to be true for Pogačar, at least so far.

What else can he do?

To finally conquer San Remo, Pogačar will need to add a new chapter to his growing legend..

He will need to arrive alone.

And a repeat of the Cipressa raid is the most likely scenario.

Assuming he doesn’t decide to attack all along the capi with 50km to go, of course.