Former New York City Mayor Rudy Giuliani spent this past weekend calling his 2016 candidate of choice Donald Trump a "genius" for potentially avoiding paying federal income taxes.
He added that voters should prefer Trump over "a woman," NBC News reported.
The comments represented the culmination of more than a year of increasingly reactionary rhetoric from a politician who was once widely viewed as a moderate Republican.
The question that pundits have been increasingly asking is why? Why would Giuliani risk his brand as "America's Mayor" by aligning himself so unapologetically with the Trump campaign, especially when so many other establishment Republicans have steered clear of it?