
In twelve days, barring a presidential pardon, Roger Stone will report to a prison where he will turn in dapper collection of suits for a significantly less-stylish jumpsuit. How does this affect you? Not at all. Should you care? Honestly? Not that much.
But it is an interesting story. So, for those of you who know nothing about a man who has a significant impact on politics in the last 40 years, let’s take a quick look at the man and his troubles and ask a question that, really, only one person really cares about: Will Roger Stone end up going to prison?
Who is Roger Stone?
Born in Connecticut in 1952, Roger Joseph Stone, Jr. is a political consultant who has been working for Republican presidential candidates since the 1970’s. He is a dirty trickster, and if you think that may be a term that is too hard or too mean, I would let you know that I just used a term that Roger Stone used to describe himself. How much does this man love the Republican party? How many other people do you know that has a back tattoo of Richard Nixon?

There are lots of stories from the myriad of campaigns Stone has worked for, but here is a quick example that I feel like solidifies his entire career: in 2008, Roger Stone created a 527 group (a political tax-exempt group) that was determined to help undermine Hillary Clinton. The group was called Citizens United Not Timid, which may not seem like anything until you realize what the acronym is.
Stone served as a presidential advisor for the Trump campaign until August of 2015, where either he quit (if you believe Roger) or was fired (if you believe Trump). Despite leaving the campaign, Stone still continued to be a vocal supporter of Donald Trump.
Why is Roger Stone going to prison?

On January 25, 2019, FBI agents arrested Stone on seven charges: one count of obstruction, five counts of false statements, and one count of witness tampering. How did Roger handle this? Well, he posted a picture on his Instagram with a picture of the judge with rifle scope crosshairs. The judge, Amy Berman Jackson, immediately imposed a gag order.
There could be a whole thing written about the trial, because it was a fucking circus. Here’s all you need to know. Stone claimed that this was all political bullying and that he would be free and vindicated. Prosecutors, Judge Berman Jackson, and a jury all disagreed, convicting him on all seven counts. Prosecutors suggested Stone be sentenced for seven to nine years.
Then, the circus came back into town… well, court.
The President tweeted immediately following the sentencing recommendation calling it unfair and the Department Of Justice, now being run by Trump lackey William Barr, removed the sentencing. Did the prosecutors of the Stone case take that action well? They did not and all resigned. Eventually, Stone was sentenced to 40 months in jail. Appeals were made and denied. Stone claimed that being in prison would put him at increased risk to become infected with COVID-19, a claim which seemed odd considering that the prison he is to enter has had zero cases. Stone is set to surrender himself on July 14th.
That leads us to our last question.
Will Roger Stone go to jail?
Let’s just start by saying this: when you constantly dress like an Adam West-era Batman villain, you probably will not do well in prison.

Roger Stone is set to be a 67-year old inmate, which isn’t a great year in one’s life to begin a new career choice as “dude in prison”. But will he see a jail cell. Honestly, it still feels like a coin toss.
Stone has a reputation for knowing where all the bodies are buried, and because he worked for Trump, he has to know things. I find it hard to believe he hasn’t leaned on people and not-so-subtly explained that he will sing like a damned canary unless he gets pardoned. On the other hand, I don’t know what Trump is waiting for. He’s had months where he could have easily stepped in and commuted the sentence or pardoned Stone outright and he hasn’t. Maybe there’s some reason why Trump is waiting; I have speculated that he is waiting for really horrible news to drop so he can issue the pardon the next day as a way of damage control. Honestly, who knows?
Like Roger Stone, all we can do is wait and see.