Call me biased—and you’d be correct—but I have a problem with adding Lincoln’s assassin to this list. Indeed, in his place one will find mass murderers, colluding colleagues, and some of the worst kinds of racists (those with a pedestal), but I’ve bought into the infallible Lincoln lore and cannot bring myself to post John Wilkes Booth, no matter how handsome he was. So imagine how pleased I was to find—while finally reading Sarah Vowell’s Assassination Vacation (the last pie-chart fact I attribute to her research)—that John had a brother who could be deemed a winner. Thus, a compromise:

HISTORIC BONER NO. 19 Edwin Booth, American stage actor

The Evidence:

I just feel bad for Edwin, losing his first (and then second) wife, having to publicly deal with the brotherly association that caused him to momentarily abandon his career. But if that does nothing for you, maybe this will melt your heart a bit.

Next Time: ???