The Way George Conway Trolls Trump Might Make His Political Affiliation Hard To Believe

Given the president's penchant for Twitter, many have similarly taken to the social media platform to troll Donald Trump, including the husband of one of his senior advisers. Indeed, some recent tweets may have caused people to wonder if George Conway is a Democrat, as Kellyanne Conway's husband has certainly not held back when it comes to critiquing Trump online. While George Conway's colleagues characterize him as a conservative, according to The New York Times, his tweets about Trump seem to imply a disapproval of some of the current administration's actions.

Back in March, the Huffington Post reported that around half of Conway's tweets and retweets that month had been critical of President Trump. For example, on March 23, Conway retweeted a tweet from Politico's managing editor, Sudeep Reddy. Reddy had shared a quote from an article critical of Trump that said, "Trump's habit of overpromising and underdelivering has created a credibility gap unknown to the presidency in the modern era."

As The New York Times reported, more recently, Conway shared a tweet from Times writer Shane Goldmacher, who had tweeted an article from The Wall Street Journal along with the quote, "Trump should worry that Americans will stop believing anything he says."

In its May 6 article, The New York Times sought to delve more deeply into the potential reasoning behind Conway's tweets, asking whether he is truly at conflict with the administration for which his wife works or if he, as a lawyer, is simply commenting on what he sees as potentially problematic legal issues.

As the paper reported, the Conways declined to comment on the issue. So, to inform its article, The New York Times interviewed some of George Conway's friends and colleagues, who characterized him as an intelligent and shrewd lawyer and also as a conservative. Lisa Blatt, a fellow lawyer who has known Conway for six years, told the paper, "He’s one of my most conservative friends. ... He hasn’t changed that much to me since before Trump was even a candidate.”

Other friends have similarly described Conway as a conservative, but also as being open to other vantage points. As his law school classmate David Wecht, a Democrat, told The Washington Post in May 2017, “George was already an outspoken conservative when I met him in law school ... But he was always willing to debate, always receptive to other arguments. My most delightful exchanges in law school were probably debating him at Federalist Society meetings.”

Conway himself also indicated in the same article that he sometimes deviates from what is expected, telling the paper, "I have contrarian tendencies." Thus, perhaps these tendencies somewhat explain his willingness to be critical of Trump, despite his previously espoused conservatism.

For her part, Kellyanne Conway has been highly critical of any queries into the impetus behind her husband's tweets. For example, in April CNN host Dana Bash asked the counselor to the president about her spouse's tweets and Conway offered condemnation in response. She accused Bash of trying to “harass and embarrass” her and said in reply:

It’s fascinating to me that CNN would go there. ... You just brought him [George] into this, so this ought to be fun moving forward. We’re now going to talk about other people’s spouses and significant others just because they either work at the White House or at CNN? Are we going to do that? You just went there.

Overall, while George Conway is known as a conservative, his tweets critiquing the Trump administration have certainly drawn attention. Time will tell if Conway continues to share these critical tweets — and whether or not he will eventually comment on the motivation behind them.