Will's retail political approach, with his blatant honesty resonates with people. It's what Trudeau needed, that credibility of a man known to sit down, say
"Look this is all screwed up, here's why it is screwed up, and here's what I am going to do to try to fix it. If you want that, vote for it. If there is a better option for you, vote for them. But get out there and decide."
It's why, in Carter's Order, Trudeau is relying so heavily on Will to bail the party out of scandal. And why, when it backfires on the Prime Minister, things go badly.