Would be a suicide, after Colombo only van Avermaet in 2011 was able to survive the Poggio (and he was still catched after the descent) after attacking on the Cipressa and in 2011 was a crazy race with a very reduced gruop of 30/40 riders in front already after the Altopiano delle Manie and then an all out chase to not be catched by the peloton so there weren't team mates left. In a normal Sanremo nowadays it's totally impossible to attack for the win on the Cipressa with teams that organize themselves on the Aurelia, if no one tries anymore is because in the 00s the best hilly classics riders and even climbers tried year after year and were always catched on the Aurelia or at the beginning of the Poggio.I'd like to see him do a "Colombo" on Cipressa. If he could pull that of, I'd consider him the greatest classics rider since De Vlaeminck. His classics win are often done with a long-range attack. Why not in MSR?
On Poggio, he should be able to follow the favorites. But in a reduced sprint against the likes of MVDP, Van Aert, Trentin, Matthews, Sagan and Alaphilippe.. I'd be nearly impossible.
Gilbert best hope to win is a late attack on the flat like Cancellara or Pozzato, in a little gruop the possiblity to slip out in that way are pretty high because there is a moment in which everyone watch themselves at the end of the descent not wanting to pull for the others, this year without van Aert killing his chances to cactch him probably Trentin would have succeded in that and with the number of riders interested in taking the sprinters out of contention the little group after the Poggio will be the likely scenario again in the coming editions (well, if they won't cut the Poggio).