This tweet marks the first time that Conway spoke out publicly against the Trump administration, according to Business Insider, by calling Trump's Twitter antics "sad." Conway later walked back on this a bit, confirming that he did support the president's policies, as well as the administration itself. Oh, how times change.

In January, Conway clapped back at an especially lyrical tweet by POTUS, which said, among other things, that the U.S. had to "BUILD THE WALL AND CRIME WILL FALL!"

In response, Conway offered a similarly clever rhyme, with some alliteration to boot: "reciting risible rhymes won't get you a dime."

In February, Conway responded to one of the president's all-caps tweets, which read, "THE RIGGED AND CORRUPT MEDIA IS THE ENEMY OF THE PEOPLE!"

Conway replied, "The Lord made Sunday a day of rest. You could at least take one day off from debasing your office."

In one of his more interactive forms of public criticism, Conway invited Twitter users to participate in a poll in February after Trump tweeted that The New York Times was the "ENEMY OF THE PEOPLE!". The poll asked users to choose "who" had more "credibility": The New York Times, or the president.

Users overwhelmingly voted in favor of the news publication, with over 210,000 users participating and 93% of them supporting The Times.

The day after the Christchurch shooting in New Zealand took place, Trump tweeted his condolences, saying in part, "We stand in solidarity with New Zealand." However, several hours before he made any mention of New Zealand, Trump had released a slew of tweets earlier in the day about the pending Mueller Report, tweeting in part, "THIS SHOULD NEVER HAPPEN TO A PRESIDENT AGAIN!"

Given that many people often use the phrase "Never again" when responding to mass tragedies like that of the Christchurch shooting, this struck many people as deeply inappropriate. Conway acknowledged a tweet by Jameel Jaffer, Director of the Knight First Amendment Institute at Columbia University, which read, "This is not the 'never again' tweet one would have hoped for this morning." Conway added, "We know his priorities."

In a not so subtle moment of shade, Conway tweeted the cover and two interior pages of a mental health textbook. Those pages detail the symptoms of narcissistic personality disorder; Conway has accused the president of being a narcissist on a number of occasions. He provided no caption for these tweets; he must have thought they speak for themselves.

As for what licensed experts think, there are some doctors who have publicly affirmed their belief that Trump has this disorder, and other doctors who've disagreed with that diagnosis. This RollingStone article details the reasoning behind several doctors' belief that Trump does have narcissistic personality disorder; this op-ed for Stat News features a doctor who argues that Trump does not meet the criteria for that disorder.

To be clear, Conway knew Trump far before he ever became president; he and his wife met Trump when they were living in Trump World Tower in New York in 2001, according to The Washington Post.

However, the lawyer tweeted that the first time he "really understood" POTUS happened after he read a Rolling Stone article about the state of the president's mental health. Conway tweeted to Trump, "Once someone understands narcissistic personality disorder, they understand you —and why you’re unfit and incompetent for the esteemed office you temporarily hold."

This tweet was particularly dramatic, because it involved one of the few moments where POTUS hit back at Conway online. Upon seeing that the president had called him a "stone cold LOSER," among other things, on Twitter, Conway replied in true Conway fashion. He wrote, "You. Are. Nuts."

In March, Conway spoke to The New Yorker about how he believed it was important to view the president through "the prism of his narcissism", because he thinks it allows you to understand his actions more clearly. In a thread that linked to this piece, Conway wrote, "Don’t assume that the things [POTUS] says and does are part of a rational plan or strategy, because they seldom are. Consider them as a product of his pathologies, and they make perfect sense."

Conway added in another tweet, "He lies even when it makes no sense to lie. As one of his lawyers once told me, "Trump couldn’t be allowed to talk to Mueller because “he’d lie his *ss off"... So the two keys to understanding Trump are narcissism and compulsive prevarication."

In March, Conway called out two aspects of Trump's character at once. Conway was responding to a report that detailed the apparent confusion Trump aides were having over why Trump was "picking fights" with the late Sen. John McCain months after his death. Conway wrote, "oh they full well know #notstable#notagenius"

Though Trump has never directly acknowledged Conway's particular tweets regarding mental health, he has defended questions about his mental health in the past. In June 2018, following the release of Michael Wolff's book, Fire and Fury: Inside the Trump White House, Trump tweeted that he was "a very stable genius," among other things.

In the beginning of April, while delivering remarks at the National Republican Congressional Committee's annual spring dinner, Trump attacked wind power in a particularly confusing way. He said, “If you have a windmill anywhere near your house, congratulations, your house just went down 75 percent in value. And they say the noise causes cancer." He provided no evidence for his claim.

Since then, a number of people including Conway have mocked the president for the unsubstantiated claim. Conway changed his Twitter bio to "windmill cancer survivor," and also tweeted a faux-speech by Trump. The speech read,

Hillary wanted to put up wind. Wind. If you―if you have a windmill anywhere near your house, congratulations: Your house just went down 75 percent in value. And they say the noise causes cancer. You tell me that one, OK? ‘Rrrrr, rrrrr’―you know the thing that makes the― .. it’s so noisy. And of course it’s like a graveyard for birds. If you love birds, you’d never want to walk under a windmill because it’s a very sad, sad sight. It’s like a cemetery. We put a little, we put a little statute for the poor birds. It’s true. You know in ....... California, if you shoot a bald eagle, they put you in jail for five years. And yet the windmills wipe ’em all out. It’s true. They wipe ’em out. It’s terrible.

Conway sometimes writes lengthy criticisms of the president, but just as frequently he can make his feelings clear with a single word or retweet. In this instance, Conway made his feelings about potential presidential impeachment by tweeting one word: "Aye."

This comment came on April 23, in response to a tweet by Washington Post reporter Josh Dawsey, which read,

The president spent this morning complaining he is unfairly treated by “Psycho” Joe Scarborough, CNN, the New York Times, its “stupid” columnist Paul Krugman, Twitter, Democrats, the media & more. He called for the “enemy of the people” NYT to get on knees and apologize to him.

Conway quoted the tweet and added, "Perfectly normal behavior for a psychologically well-adjusted person."

In April, Conway asked his Twitter users to consider "a simple point" in pair of tweets. The point was delivered in the form of a question: "Do we have a president who is loyal to the country, or loyal only to himself?"

Conway explained, "When you put the question that way, and the object of the question is Donald J. Trump, now that we know all that we know about him and have seen all that we have seen, there can only be one answer."

In response to a tweet by Trump that addressed both the Mueller report and his claim that he "DID NOTHING WRONG" (though he didn't make clear what accusation in particular he was defending himself from), Conway wrote,

(1) You’re lying again. (2) It’s astounding how little understanding you have of the Constitution you’ve sworn to uphold.

Conway then retweeted his response to make sure it would show up on his own feed, front and center.

Conway sent the hashtag #DerangedDonald into viral territory earlier this month. The nickname began to trend after Conway posted a trio of tweets on April 25, which read in full,

Deranged Donald is at back at it again. Deranged Donald can do things like this and it’s not even the top of the news, because it gets lost beneath all of the other deranged things Deranged Donald does. #DerangedDonald...Deranged Donald has this neat job where he’s supposed to receive and read books with more accurate, highly valuable, top secret information, but he doesn’t like those books unless they have lots of pictures and tell him how great he is. #DerangedDonald...Plus Deranged Donald doesn’t really need all those books because Fox News. #DerangedDonald

For anyone wondering what might have inspired Conway to congratulate the president (as seen in the tweet above), you probably wouldn't be surprised to know that the congratulations were definitely tongue-in-cheek. Conway was congratulating POTUS in response to a tweet by The Washington Post on April 29, which stated that Trump had officially surpassed "10,000 false claims during his presidency."

In a pair of tweets, Conway wrote of the "historic milestone,"

An amazing accomplishment!! No one but you could have achieved this. Not just the number. Covering all topics, never shying from even the most brazen, disprovable lies, you’ve even managed to tell multiple lies on same subject, lying even about lying!!

In an interview with The Washington Post in March, Conway explained why he tweets so much about the president, especially given the fact that his wife is a top Trump advisor. “It’s so maddening to watch," Conway said. "The mendacity, the incompetence, it’s just maddening to watch."

He concluded, "The tweeting is just the way to get it out of the way, so I can get it off my chest and move on with my life that day. That’s basically it. Frankly, it’s so I don’t end up screaming at [my wife] about it." And if you couldn't already tell, his tweets make his feelings about POTUS very clear.