Roose, by a long shot. He has the long-term smarts that helped him move things towards his own higher positioning and, eventually, the Stark downfall.
- He deliberately threw the Battle of the Green Fork, killing off or making captive many of his neighbours.
- He had his bastard seize Lady Hornwood’s lands, thus keeping Manderly from it.
- He betrayed Robb Stark outright when he sent an army to go down in terrible defeat at Duskendale.
- He let Jaime go when he knew Robb was looking for him.
- He was one of the main architects of the Red Wedding.
- His son, almost certainly with his approval, sacked Winterfell and wiped out another northern army.
And he did it all with plausible deniability. Once the secret was out, he was Lord of the North and ally of the Iron Throne.
All that took. planning, patience and deep political smarts. People around him don’t trust him. He scares them with his quietude and lack of emotion. But that is not a bad thing when you have power.
Ramsay, by contrast, has in-the-moment smarts. He spends his time being cruel to people, torturing them and making them fear. As a result he has to be keenly observant of his victims, gauging how far he can push them; always on the lookout for the knife in the back. He has to play his minions against each other, using the overall fear of him to manipulate them into sucking up to him. This is also kind of a political thing, but it is very limited to his personal surroundings; overall his devil-may-care attitude about who finds out about his monstrosities is his downfall. Anybody NOT in his immediate power just hates him and would never follow him.
Roose wins this one by a mile. Even if Ramsay ends up killing him, as it was in the show, we definitely can say that Roose had a longer run terrorizing his own country, raping the peasants with impunity, flaying the occasional human for sport than Ramsay will ever have.
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