These twin defeats find Trump failing both as a political leader and as the master of the social universe where, legend had it, he could not be bested.
The Twitter loss came first, as Gillibrand called for Trump to resign because of allegations of sexual misconduct lodged by more than a dozen women. How did Trump reply? With the Twitter version of sexual misconduct.
According to the President, Gillibrand would "do anything" for political donations. The senator responded with measured defiance, declaring she would not be deterred. In this #metoo moment, when women are pushing back so powerfully against sexual harassment, it was an easy win for Gillibrand.
Indeed, Trump made it easy for her when he sent press secretary Sarah Sanders out to tell reporters that their minds were "in the gutter" if you think Trump was saying the senator was willing to trade sex for cash.
As Sanders spoke, USA Today was preparing to declare that Trump had "all but call[ed] Senator Gillibrand a whore" and that this act showed he's "not fit to clean the toilets in the Barack Obama Presidential Library or to shine George W. Bush's shoes."
When USA Today descends to editorializing about a president unfit to clean toilets then you know something astounding is at hand. In this case, the editors were pushed to an extreme by a man who has made extremism a way of life in business, politics, and now government.
Extreme is the only word that applies to Trump's behavior in the Alabama race, as he threw his wholehearted support to a man who stood accused of sexual misconduct with a 14 year-old girl and dating -- or attempting to date -- several teens. And yet there Trump was, delivering a speech to boost Moore in the border city of Pensacola and recording a message urging voters to send him to Washington DC.
All the President had to do to avoid the ignominy of Moore's defeat was to listen to his daughter Ivanka who said, days ago, that a "special place in hell" awaits men who do what Moore was credibly accused of doing.
However, he followed instead the lead of his former campaign manager Steve Bannon, who appeared in Alabama on Moore's behalf and has long fomented revolution against the president's own party.
Having followed Bannon's lead instead of his daughter's and indulging his own Twitter habit, Trump made himself into the kind of figure he despises: a loser. Twice.
As Trump was bested by the forces of decency, he also brought peril to his party, by getting on the wrong side of women nationwide.
This outcome will only embolden Republicans who have chafed at Trump's style and leadership thus far and make life more difficult for him in days to come.