Let's say that politically you lean towards the alt-right. Is it better for Trump to win or lose?
If you think he is legitimately pro-white, pro-male, and/or anti-PC and would be a really competent & decent president who will do a lot of good, of course you want him to win.
If you think he is going to be a joke of president who will make Obama look principled and restrained with stuff like
>sending American troops into stupid wars
>breaking international laws
>killing Edward Snowden
>changing his opinion based on the political winds while spewing constant bullshit
then you obviously do not. It's not only bad in and of itself, but it also reflects badly on your views within the culture.
If you were to go back 10 years, when Bush and Cheney were in power, being progressive was popularly seen as something cool and anti-establishment. There was relatively little of what would be called racism online, other than on Stormfront, VNN, Majority Rights, and a few smaller sites.
Fast forward to today, and pretty much the entire culture of what makes up /pol/ and the contemporary alt-right, for better or worse, blossomed during the Obama administration. Being progressive/liberal is a little embarrassing outside of insular hugboxes like Reddit and Tumblr, and the worst of the progressives, SJWs, are widely reviled across the internet.
The point is that you have to look at the overall effect within a culture.