His latest comments come after Trump publicly attacked Conway on Twitter , calling him "a stone cold LOSER & husband from hell!"
Here's a brief history of George Conway's transformation from Trump supporter into one of his most visible and vocal critics on the right.
June 2, 2017: Conway turns down administration role
Chip Somodevilla/Getty Images
After speculation began in March 2017 that Conway would be picked for a position in the Trump administration, Conway eventually declined any administration role, saying :
"I am profoundly grateful to the President and to the attorney general for selecting me to serve in the Department of Justice. I have reluctantly concluded, however, that, for me and my family, this is not the right time for me to leave the private sector and take on a new role in the federal government."
Conway went on to clarify: "Kellyanne and I continue to support the President and his administration, and I look forward to doing so in whatever way I can from outside the government."
The Washington Post reported that Conway considered the role, but was scared off by Trump's firing of FBI Director James Comey and the aftermath that ensued.
June 5, 2017: Conway posts his first critical tweet
Associated Press/Manuel Balce Ceneta
Shortly after turning down an administration position, Conway started to tweet critically of Trump.
In his first post , he questioned the usefulnessof Trump's tweets, mocking Trump's signature sign-off "Sad!"
In a later tweet, Conway clarified that he still supported the president.
March 28, 2018: Conway gets more vocal on Twitter
In late March 2018, after nearly a yearlong hiatus, Conway called Trump's reported interest in pardons for former staff as a way to protect himself from the special counsel Robert Mueller's investigation " flabbergasting ."
Also at this time, Conway reportedly switched his party registration to "unaffiliated."
March 29, 2018: Conway deletes some critical tweets
According to a CNN report , Conway deleted a series of tweets after his March tweets gained attention. The deleted tweets reportedly included one that called the president "absurd."
April 22, 2018: Kellyanne Conway spars with Dana Bash over her husbands tweets
Kellyanne Conway sparred with Dana bash after the CNN host asked her about her husband's tweets.
May 3, 2018: Conway calls out Rudy Giuliani
Cuomo Prime Time/CNN/Twitter
Conway tweeted a section of the Federal Election Commission's website the night after Trump's personal lawyer Rudy Giuliani revealed that Trump reimbursed his former attorney for a $130,000 payment to porn star Stormy Daniels.
May 17, 2018: Conway Calls Giulianis argument drivel
In a Reuters piece on Giuliani's claim that Mueller can't subpoenaTrump, Conway went on the record calling the assertion "drivel."
May 24, 2018: Conway reportedly coaches anti-Trump writers
Pablo Martinez Monsivais/AP
A Politico report alleged that Conway had emailed multiple writers who have been critical of Trump to help improve their arguments.
June 11, 2018: Conway publishesa pro-Mueller essay
Lawfare published an essay from Conway criticizing arguments against the appointment of the special counsel Robert Mueller.
Conway wrote: "It isn't very surprising to see the president tweet a meritless legal position, because, as a non-lawyer, he wouldn't know the difference between a good one and a bad one."
Earlier in June, Conway tweeted about the same topic:
The previous June, Conway was playing a very different tune, openly questioning the Russia investigation along with his wife on Twitter:
July 9, 2018: George says hes given Kellyanne a hard time about Trump
Pablo Martinez Monsivais/AP
For an article about public heckling of Trump administration figures, George told the WashingtonPost that "She has been getting a harder time from me about working for this administration than walking down the street."
August 15, 2018: The Conways open up about their marriage
In a Washington Post article about the couple, the Conways lamented the effect their political division was having on their marriage.
Kellyanne told Post reporter Ben Terris that George's tweeting was "disrespects hiswife."
George said he was "saddened by how things turned out" with the administrationand that he regretted initially introducing Kellyanne to Trump.
"I feel there's a part of him that thinks I chose Donald Trump over him," Kellyanne said. "Which is ridiculous. One is my work and one is my marriage."
September 27, 2018: The retweet era begins
Tom Williams-Pool/Getty Images
In the months following the profile, Conway primarily communicated through retweets.
For example, in late September, he retweeted posts that were both critical of Trump and supportive of then-Supreme Court nominee Brett Kavanaugh:
October 30, 2018: Conway rejects Trumps justification for outlawing birthright citizenship
According to Conway, "the challengers would undoubtedly win."
Conway and Katyal point out that the right to citizenship is written into the 14th Amendment:
"All persons born or naturalized in the United States, and subject to the jurisdiction thereof, are citizens of the United States" except in two cases: children of "alien enemies in hostile occupation" and the children of foreign diplomats.
To change this, they argue that you'd need a Constitutional Amendment.
November 8, 2018: Conway co-authors an op-ed arguing Trumps attorney general appointment is unconstitutional
"Trump's installation of Matthew Whitaker as acting attorney general of the United States after forcing the resignation of Jeff Sessions is unconstitutional. It's illegal," they wrote. "And it means that anything Mr. Whitaker does, or tries to do, in that position is invalid."
Whitaker had been critical of the Mueller probe, and many, including Conway, accused Trump of installing him to oversee the Justice Department in order to squash the investigation.
Conway and Katyal continued:
"Because Mr. Whitaker has not undergone the process of Senate confirmation, there has been no mechanism for scrutinizing whether he has the character and ability to evenhandedly enforce the law in a position of such grave responsibility. The public is entitled to that assurance, especially since Mr. Whitaker's only supervisor is Mr. Trump himself, and the president is hopelessly compromised by the Mueller investigation. That is why adherence to the requirements of the Appointments Clause is so important here, and always."
November 16, 2018: Conway railed against Trump in a podcast interview
Georgetown Law/Handout via REUTERS
"I don't feel comfortable being a Republican anymore," Conway said on the podcast. "I think the Republican Party has become something of a personality cult."
Conway described Trump's tweets criticizing former Attorney General Jeff Sessions as "appalling," and a sharp deviation from political norms.
"We're talking about someone who has sworn an oath to uphold the Constitution and laws of the United States," Conway said, "and to criticize the attorney general for permitting justice to be done without regard to political party is very disturbing."
Conway also revealed more details on why he didn't take the Trump administration job.
"I'm watching this thing, and it's like the administration is like a s---show in a dumpster fire," he said on the podcast. "And I'm like, 'I don't want to do that.'"
David Choi contributed reporting.
December 3, 2018: Conway accuses Trump of witness tampering
In December, former Trump campaign adviser Roger Stone said he would "never" testify against the president as part of the Mueller investigation. Stone was indicted on seven counts of obstruction, false statements, and witness tampering, and is pleading not guilty.
In a tweet , Trump praised Stone for not willing to be "forced by a rogue and out of control prosecutor" to "make up lies and stories" about the president. He added that it was "nice to know that some people still have 'guts!'"
John Haltiwanger contributed reporting.
March 18, 2019: Conway questions the presidents mental state
Their tense relationship reached a fever pitch after Trump spent St. Patrick's Day weekend on a Twitter tear against "Saturday Night Live," Fox News, and the late Sen. John McCain.
When asked about the tweet , Kellyanne said she doesn't "share those concerns" about Trump's psychological state.
March 19, 2019: Trump calls Conway "A total loser!"
Georgetown Law/Handout via REUTERS
Trump finally broke his silence on Conway's criticisms when he called the lawyer "A total loser!" on Twitter .
Conway responded with several tweets of his own, starting with, "Congratulations! You just guaranteed that millions of more people are going to learn about narcissistic personality disorder and malignant narcissism! Great job!"
"This was the article that first got me to really understand you, @realDonaldTrump," Conway continued in another tweet , with a link to a Rolling Stone story about Trump's mental health. "Once someone understands narcissistic personality disorder, they understand youand why youre unfit and incompetent for the esteemed office you temporarily hold."
March 20, 2019: Trump calls Conway "a stone cold LOSER & husband from hell!"
Trump escalated the feud, calling Conway "a stone cold LOSER & husband from hell!"
Conway retweeted it, with the comment, "The President of the United States."
To that, George responded, "It isn'texcept perhaps to the extremely juvenile and boorish. What I really wouldn't want to be called is 'Individual-[ ],'" referring to the way Trump is characterized in Muller's court filings.
In an interview with Politico , Kellyanne said she had discussed George's criticisms with Trump "in passing," and that the president "left it alone for months out of respect for me." She added that the rift hasn't affected her job in any way.
"But you think he shouldnt respond when somebody, a non-medical professional accuses him of having a mental disorder? You think he should just take that sitting down?" she told Politico's Daniel Lippman, adding that Trump was a "counterpuncher."
Asked how his tweets reflected on first lady Melania Trump's "Be Best" anti-bullying campaign, Trump said he didn't know Conway and called him "a whack job."
"He's doing a tremendous disservice to a wonderful wife," Trump told reporters. "Kellyanne is a wonderful woman. And I call him 'Mr. Kellyanne.' The fact is that he's doing a tremendous disservice to a wife and family. She's a wonderful woman."
March 21, 2019: Conway doubled down on his questions about Trumps mental health
After Conway called Trump " dumb " in tweets, he retweeted someone who wondered, "Could be cognitive decline rather than simple stupidity," and shared an interview from 1980 when Conway said Trump was "articulate and coherent, unlike today."
"He lies even when it makes no sense to lie," Conway tweeted . "As one of his lawyers once told me, Trump couldn't be allowed to talk to Mueller because "he'd lie his a-- off.'"
Retweeting a Talking Points Memo story with the headline, "Trump's aides have no idea why their boss keeps picking fights with a senator who died almost seven months ago," Conway added : "oh they full well know #notstable #notagenius."
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