Do you think he can win?

Nope
Trump already passed tax reform on the middle class and it saved most of us around 10-15k in taxes. Bernie will raise taxes for the middle class by 30k all in the name of shittier everything. Most corporations and the rich will leave the country.

Bernie will also absolutely require things like cryptocurrency get banned so he can fuck platforms like steemit, Dlive and LBRY over. Cryptocurrency makes it too easy to hide from his super high taxes so Bernie will be freaking out over this kind of shit.

Also, most people don't give a fuck about socialism. Most people only care about their own self interests. It sounds great at first but in practice nobody wants to do it if it means they themselves will have to pay more.

Bernie would get destroyed.