Will Roger Stone Flip on President Trump?

By in Politics on

The Donald Trump presidency has been nothing if not dramatic. It seems as though new compelling storylines emerge every day from this administration. Plenty of the news tends to be unfavorable to the man currently occupying the Oval Office, of course.

The president, his administration, his inauguration, his foundation and even his inauguration have all been subjected to various investigations. The most notable probe involves whether Trump’s campaign was working in concert with a foreign entity in order to help improve his chances of getting elected back in 2016. Shortly after Trump made the bold decision to fire FBI director James Comey, Congress voted to appoint a Special Counsel to investigate the president’s dealings during the lead-up to Election Day.

That Special Counsel, former FBI director Robert Mueller, has been on the job since May of 2017. Since then, a number of indictments and convictions have come down via Mueller’s office, though we are still waiting on his final findings. Several people with close ties to the president have been charged, including his former campaign chairman (Paul Manafort) and his longtime personal attorney (Michael Cohen).

Another Trump associate currently facing charges is Roger Stone. Stone has been a political consultant around Washington D.C. for decades, and he has been a vocal supporter of Trump’s since the latter announced his candidacy for president in 2015. On January 25 of this year, Stone was apprehended by FBI agents at his home in Florida before being charged with several crimes, including witness tampering and obstructing an official proceeding. Stone was also slapped with 5 counts of making false statements under oath.

Stone has pleaded not guilty to any wrongdoing. Unlike some of the others that have been charged by Mueller’s office, it seems as though Stone plans to fight the charges rather than cooperate with investigators.

Trump’s presidency has brought forth plenty of betting opportunities, and the Stone story is the latest. MyBookie has a couple of Stone-related prop bets posted. Why not try and make a little money wagering on what will happen? Let’s dive right in.

Will Roger Stone Flip on Donald Trump?

  • Yes +300
  • No -500

As mentioned, a number of people with ties to Trump have already been chased down by the special investigation. Here are those people and whether they wound up cooperating with investigators as they stared down the possibility of serving time:

Charged Did They Cooperate? Jail Time?
George Papadopoulos Yes 14 days in jail
Paul Manafort Yes Facing 25-plus years
Rick Gates Yes No
Michael Flynn Yes Awaiting sentencing
Richard Pinedo Yes 6 months in jail
Alex van der Zwaan Yes 30 days in jail
Konstantin Kilimnik No Awaiting trial
Michael Cohen Yes 3 years in jail
Roger Stone No Awaiting trial

Not everyone that has been charged with crimes in connection with the investigation opted for immediate cooperation. Some wanted to deny the charges and fight for their freedom before ultimately succumbing to the pressure. Once it became evident to those charged that they had a choice between cooperating for facing hard time in prison, cooperation sounded quite a bit more appealing.

Many of them, including Papadopoulos, Cohen, Manafort and Flynn, decided to flip after being caught lying under oath to investigators. Lying under oath is obviously a crime, and Mueller’s office has shown that they are willing to prosecute said crime.

Facing charges has not silenced Stone by any means. Since posting bond, Stone has made numerous appearances on television and radio advocating for his innocence. He has taken a surprisingly confident attitude toward his legal issues, though that may change some time soon.

On February 18, Stone made the curious decision to post a picture of Judge Amy Berman Jackson, the judge overseeing his case, on his Instagram page. The image included what appeared to be a crosshair near the judge’s head, and the caption called Mueller a “Deep State hitman” and accused Berman of being politically partisan. Because that was so obviously a horrible idea, Stone subsequently deleted the post and his lawyers wound up issuing a formal apology to the judge.

On February 21, Stone will face the judge in court in order to find out whether or not he could face additional charges for his actions.

The decision to issue an apology makes it clear that Stone may be sweating his legal trouble more than he has shown publicly. Once the possibility of doing real jail time becomes more evident, it wouldn’t be all that surprising to see Stone try to cut a deal with investigators in order to get a reduced sentence. The same thing has already happened with most of the others that have been charged in the probe.

Stone has been adamant that he has done nothing wrong and that he would not flip on the president. The self-described “dirty trickster” has known Trump for quite some time, so there is a decent chance he knows more about Trump’s dealings over the years than even his former attorney, Michael Cohen. Stone may say tough things publicly, but there’s no telling how he would react if the possibility of facing a lengthy jail sentence becomes reality.

As so many others before him have done, I think there is a strong chance Stone ends up seeing the writing on the wall. Whether prosecutors have interest in offering Stone a cooperation deal remains to be seen, but if it comes to pass I think it will be difficult for Stone to turn it down.

Oddsmakers heavily favor Stone going down with the ship, but I think as a bettor you have to jump all over Stone flipping at +300. Other investigation targets haven’t been shy about flipping on the president and potentially testifying against him, and I don’t see any reason to believe Stone is any different. Stone will eventually flip, so I would be betting “yes” at +300 here.

Will Donald Trump Call Roger Stone a “Liar” on Twitter?

  • Yes +300
  • No -500

The 45th president has an affinity for social media, particularly Twitter. It’s fair to wonder whether Trump makes more news with his actions or with his Twitter account. Regardless of whether the White House wants to officially comment on a story in the media, you can bet that the president will weigh-in on his Twitter account regardless. The unfiltered look at his stream of consciousness is nothing if not slightly fascinating, even if it seems to get him into hot water more often than it helps him.

His own lawyers have tried to get him to stay silent on some things, but nobody has (to this point) managed to rein in Trump’s usage of his favorite iPhone app. The president has often used Twitter to target his political opponents, namely Speaker of the House Nancy Pelosi, Senate minority leader Chuck Schumer and his 2016 presidential opponent, Hillary Clinton.

Trump also hasn’t been bashful about taking on those that used to be on his own side. One frequent target of the president’s in recent months has been Cohen, who had his office raided by the FBI before ultimately deciding to testify against his former client. Cohen’s decision to flip on Trump led to the president calling Cohen a “liar” on Twitter on multiple occasions.

If Stone ultimately does flip, what’s going to stop Trump from giving Stone the same social media treatment he gave his former personal attorney? Trump will surely try to use Stone’s checkered past against him and try to paint him as an unreliable witness that will tell investigators whatever they want to hear if it’s going to reduce his punishment.

Trump has thus far struggled to stay silent on matters he probably shouldn’t discuss publicly via social media. So, if it starts to look like Stone will give up the goods and talk to prosecutors about the president, I do believe Trump will decide to give him the Cohen treatment on Twitter.

Once again, the betting value is with “yes” on this one at +300. Because I do think Stone ultimately flips, it’s only natural to conclude that @RealDonaldTrump will eventually lash out against him on Twitter.

Taylor Smith

Taylor Smith has been a staff writer with GamblingSites.org since early 2017. Taylor is primarily a sports writer, though he will occasionally dabble in other things like politics and entertainment betting. His primary specialties are writing about the NBA, Major League Baseball, NFL and domestic and international soccer. Fringe sports like golf and horse racing aren’t exactly his cup of tea, bu ...

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