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It is absoultely true and not even disputed that Kessler, the organizer of the Unite the Right rally was a Lefist during much of the Obama administration.

These twitters are revealing, but not surprising to anyone who has previously investigated him.

The Unite the Right rally was in 2017, so the question is at what point, between his Leftist views of 2012 and his role setting up the White Nationalist Unite the Right rally in 2017 did his views change so radically? Why did they change so radically?

And equally important, was his massive switch in viewpoints sincere, or is he, as some have speculated, a paid Deep State operative whose real goal was to create a massive "shit show" to further animosity, social distrust, and defame Trump?

From the tweets we see that in 2012 he as still an Obama-loving leftist. And still in April, 2015 he's praising Obama and John Kerry, without a spec of reservation.

In 2015 he was 32. What leads a 32 year old man to go from an outspoken Obama supporter to a White Nationalist?

His Wikipedia bio contains this information:

In November 2016, he revealed lewd and offensive tweets made by Charlottesville vice-mayor and councilman Wes Bellamy. Bellamy, who is also a teacher at Charlottesville's Albemarle High School, first drew criticism from Kessler when he called a press conference to call for the removal of the Robert E. Lee statue in Charlottesville in March 2016. In December, Kessler began circulating a petition demanding that Bellamy resign or be removed from office.[10] During the ensuing investigations, Bellamy voluntarily resigned from his teaching position at Albemarle High School in December 2016.[11]
In January 2017, while attempting to gain signatures for his petition Kessler was arrested for misdemeanor assault after punching a man in the face. He pleaded guilty and was sentenced to 50 hours of community service.[12]

So, he had some major events happening and his real political activism began in 2016. What were the events around that? Who was his antagonist? Who is Wes Bellamy?

Wes Bellamy, former Vice Mayor of Charlottesville

Per Wikipedia:

Wes Bellamy, Biography
Bellamy moved to the Charlottesville area in 2009 to work for the National Ground Intelligence Center. He left that position shortly afterwards and began teaching in Albemarle schools. [3] He established the Helping Young People Evolve in 2011 and soon afterwards entered city politics.

Bellamy is still on the City Council of Charlottesville. What were the tweets that Kessler brought forward, that forced Bellamy out of his teaching job?

We find in this article (linked as #14 on his Wikipedia bio) that Kessler discovered and was infuriated by Bellamy's tweets which, per the article: "Homophobic, sexist, anti-white language abundant in Charlottesville vice mayor's tweets"

. Let's look at a few of them:

“I DONT LIK WHIT PEOPLE SO I HATE WHITE SNOW!!!!! FML!!!!” he tweeted in Dec. 2009.
“Word...RT: TAXSTONE: Eat it while she asleep if she moan it aint rape,”

Several tweets also linked white women to rape accusations, and one retweet said white women “smell like future assault charges n deli meat.”
OK, so is it possible a fully indoctrinated liberal, Obama supporting young adult -- someone who grew up believing in equality, anti-racism, the plight of blacks suffering from discrimination, could make a hard turn in his political beliefs as a result of encountering a blatantly racist black man who holds not one, but two, very important positions of authority in the city you have lived your whole life in, and further is supported by the (mostly black) city establishment and (mostly black) city voters even after his horrific comments are made public by you?
Is that possible? Or, is it more likely the CIA/FBI recruited him and set him up to pull off the Charlottesville shit-show?
The non-conspiracy theory seems extremely adequate to explain his change in views. In fact the far-right is full of people who were once liberals who had some sort of awakening. Their is a term for it "taking the red pill" or being "red pilled". There are many red pills on many topics.
The first use of the term was by Men's Rights Advocates, many of who had been deeply screwed in divorces, and who came to see the "feminist" movement and "woman's rights" as completely wretched movements. They became "red pilled" on questions of gender, and many as a result re-evaluated their entire political outlook and became right-wingers (often Libertarians of a particular sort).
Occam's razor suggests a similar path of radicalization for Kessler.

Now, if I can figure this out, or at least make a very plausible educated guess about Kessler's background, where is Dinesh, and why isn't he explaining any of this, but instead insisting the Kessler is really a leftist?

Is he lazy? Did he actually interview Kessler?

I don't know. But when someone with a huge platform continues, over and over again to make simple mistakes...

(and, lets face it his campaign contribution cheating was a simple mistake, which led to his felony conviction, overturned by Trump's presidential pardon. It probably was an unfair prosecution, but it was also a obviously completely unforced error and lapse of basic ethical behavior)..

has he learned nothing from this?

Or is he a glib hustler, who doesn't really care about the truth as much about making a splash and feeding his audiences half-truths that they might enjoy.

Sadly, my own view of him has soured considerably over the years and I no longer value or really trust his opinions, I find that very often he's playing fast and loose with the facts, or is torturing history and logic for his own reasons.

He is not a reliable guild for true conservatives, who have always placed a very high value on truth and fairness.