Well, if the goal is to be president, and you win, I think it's hard to say your campaign was "bad". Likewise, if the goal is to become president, and you lose, I think it's hard to say your campaign was "good".
Now, what if you run a bad campaign, but your opponent runs a worse campaign and you win...relatively speaking, you ran a good campaign as it wasn't worse than your opponents. But it could still be a bad campaign. I think Trump's win definitely falls into this category...the difference in PA (20 electoral votes, HRC lost by 44,000 votes)), Wisconsin (10 electoral votes, HRC lost by 23,000 votes), and Michigan (16 electoral votes, HRC lost by 11,000 votes) would've swung it, and not by much! That seems like a bad campaign IMO, regardless of what "bad" campaigning Trump did. He won the goal.
If you run a good campaign, but your opponent runs a better campaign and you lose? Again, relatively speaking, you ran a bad campaign as it wasn't better than your opponents. That said, I'd have to dig for an example.
I think this really needs to get defined in the discussion of this (nearly continual) board argument. Can someone run a good campaign and lose? Can someone run a bad campaign and still win? If so, for either, give real-life examples [and show your work].
I think if you and Hutch answer those two questions (and follow one instructive statement), it will quickly be revealed you are debating different topics at heart.