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And increasingly, some of the nation's most high-profile commentators are speculating about one slightly unconventional pick: Sen. Al Franken.
On Monday, the Washington Post published a blog post titled "Why Al Franken makes a weird amount of sense as a 2020 presidential candidate," positing that the former Saturday Night Live cast member may be the candidate best-suited to parlay Trump's barbs.
The post came just a few days after the National Journal took a similar view, hypothesizing that Franken's wit and celebrity could help rally Democrats to defeat Trump.
Other observers suggested that the Minnesota senator's recent senate battles may be priming him for a more visible role in the Democratic party.
CBS speculated before Trump was even sworn in that Franken's profile was rising following the 2016 election for taking on the incoming president's cabinet nominees.
Though it stopped short of declaring Franken a 2020 candidate, The New Republic noted Franken's longtime stint as a critic and dissembler of conservative punditry, declaring the Trump presidency "Franken's time to shine."
The media attention came on the heels of some of Franken's most high-profile actions since joining the senate in 2009. Franken went viral thrice over in January for his tough grilling of Trump's nominees to head up the departments of justice, education, and health and human services respectively, earning a label from The Hill as a "liberal force."
And he provided a bit of levity during former Texas Governor Rick Perry's hearing earlier this month when Trump's energy secretary nominee made an accidental euphemism while discussing his private meeting with Franken.
The political analyst class isn't entirely alone in its recent interest in the longtime political satirist.
The day after the election in November, a "Draft Franken" super PAC filed its first notice to the Federal Election Commission, though it hasn't raised any money for the Minnesota senator.
Intentionally or not, Franken's high-profile grillings represent a notable shift from his previous reputation in Congress and on the campaign trail.
Past political strategists decided that in order to win election and stay in the Senate, Franken needed to engage in "strategic boredom," distancing himself from past wit expressed as a comedian and liberal entertainer.
He familiarized himself with policy and declined interviews with national media outlets with the hopes of being known as a "workhorse not a show-horse." The Minnesota senator was so boring, in fact, that his 2014 Republican opponent tried to win votes by casting Franken as a guy who was "basically invisible" in Washington.
"I had years in show business and had plenty of camera time," Franken told the Los Angeles Times in 2014. "By being perceived as someone who was rushing to the camera all the time, it can undercut your effectiveness in the body."
But many observers speculate that Franken's issue set, acidic sense of humor, and Rust Belt pedigree could make him a prominent foil to Trump.
As one of the most vocal senate proponents for net neutrality, the consumer protection that compels internet service providers to ensure equal access to all websites, Franken is already on a collision course with the new administration. Trump's Federal Communications Commission chair immediately set about rolling back net neutrality rules, setting up a likely fight with the Minnesota senator.
"I have no doubt that you recognize the significance of your new role, but your stated opposition to strong net neutrality rules raises serious concerns about your commitment to honoring the First Amendment," Franken said in a statement last month. "Allowing giant corporations to pick and choose the content available to everyday Americans would threaten the basic principles of our democracy."
For the moment, the Franken candidacy still exists mostly in the imaginations of political analysts.
Asked by Business Insider, multiple Democrats working on Capitol Hill separately noted that while he's occasionally noted as a potential candidate, there's no clear sign that he's interested. Further, his potential candidacy could be complicated by fellow Minnesota Sen. Amy Klobuchar, who is more widely suspected to hold 2020 ambitions.
Many agreed that it was likely far too early for media outlets to speculate about Franken's interest.
"[It's] way too early," former Minneapolis Mayor RT Rybak told Business Insider. "I love Al as my senator, but I imagine there will be thousand of boomlets in the next couple years and about the only thing we should take seriously for the next year is how to stop Trump and win the midterms."
The Minnesota senator explicitly said he would not seek the presidency in 2020, the same year as his senate reelection.
In a statement on Tuesday, Franken's office reiterated that he would not run, saying that the senator will "spend the next several years fighting on behalf of Minnesota families."
Still, the Minnesota senator himself has entertained the possibility of a Franken presidency.
In 1999, the then-comedian released a satirical novel titled "Why Not Me?" detailing his unlikely rise to the presidency. During his imagined campaign, Franken painted his opponent as a tool of the financial industry, and managed to win the White House despite insulting Iowa voters, making outlandish yet simple campaign promises, indulging his mood swings, and being accused of extramarital affairs.
Sound familiar?