'Significant Danger' From Former Libertarian Nominee: Prosecutors

WAUKEGAN, IL — After being extradited back to Illinois to face allegations that he threatened to kill a pair of Lake County judges unless they granted him custody of his children, jailed former Libertarian gubernatorial candidate Grayson Kash Jackson now faces the prospect of a higher bond at his first local in-person court appearance Friday.

Jackson, 44, formerly known as Benjamin Winderweedle, was charged by prosecutors on Oct. 7, the same day authorities say he placed threatening phone calls to two judges who have been involved in his divorce proceedings.

Authorities in Logan County, Arkansas, where Jackson purchased a house during his 2018 campaign for governor of Illinois, took him into custody on a one-count arrest warrant on Oct. 14.

On Dec. 21, a Lake County grand jury indicted Jackson on six felony counts — two counts of threatening a public official and four counts of intimidation.

According to the indictment, Jackson not only placed threatening calls to two judges, but also called the court security office at the Lake County courthouse and threatened to kill the judges "unless the Lake County Sheriff's Office filed criminal charges against [them.]"

Jackson remained jailed in Arkansas until Jan. 14, when he returned to Illinois to be processed on the arrest warrant, which called for a $50,000 cash payment to secure his pretrial release.

Court records show Jackson's first hearing on the case was held Jan. 18 over video teleconferencing software.

At the hearing, the Lake County Public Defender's Office was appointed to represent him, but his attorney did not have an opportunity for a private discussion beforehand, according to court filings. And because Lake County judges are involved in the case, DuPage County Circuit Judge Mike Reidy is presiding over the case. DuPage County prosecutors are trying it.

Jackson first consented to the hearing being held remotely over video teleconferencing software and pleaded not guilty to the charges. At that point, his assistant public defender asked for a reduction of the bail set on the warrant, while an assistant state's attorney prosecuting the case called for it to be increased.

After the judge heard Jackson's case for a lower cash bond, prosecutors began outlining the charges. But after several minutes of argument — and immediately before prosecutors were due to play an audio recording — Jackson withdrew his consent to proceed with a remote hearing, in a move described as "gamesmanship" by DuPage County Assistant State's Attorneys Steven Lupa and Mary Fleming.

Jackson was back in court Jan. 20, and prosecutors filed a motion to hold the bond hearing remotely. His attorney said he was not ready to proceed, and the hearing was postponed until Monday, according to court records.

Prosecutors and Jackson's defense attorneys filed dueling motions arguing over whether the former gubernatorial nominee had the right to demand that Monday's hearing be held in person rather than over Zoom video teleconferencing software at this stage in the case.

After the judge granted the prosecution's request to hold a remote bond hearing, over Jackson's objection, he allowed Jackson to withdraw his request for the hearing, over the state's objection. Prosecutors then said they would file a new motion to increase Jackson's bond, which Reidy said he would hear at Friday's hearing, in person, according to court records.

Jillian Kassel and Keith Grant, Jackson's public defenders on the case, said the judge was right to allow Jackson to revoke his consent to a Zoom hearing. They said allowing the case to proceed in person would not clearly not delay the trial or impede justice.

"[N]o argument can be made that it would," they argued, "[Jackson] remains incarcerated in the Lake County Jail on a cash bail amount far in excess of his ability to post."

Related: Ex-Libertarian Gubernatorial Candidate Kash Jackson Charged With Threatening To Kill Judges

Lupa and Fleming said the current bond does not take into account the five additional charges that were added to the indictment last month, which double the maximum potential prison sentence for a conviction due to a special sentencing range for the offense of intimidation.

"[The state's attorney's office] obtained new evidence since bond was set on the original arrest warrant," they said. "This evidence includes a video statement wherein [Jackson] admits to making the phone call alleged in the indictment."

The two DuPage prosecutors said they planned to ask for an increased cash bond and additional conditions of bail.

"This information will establish that [Jackson] poses a significant danger to the community and is exceedingly likely to abscond from justice," they said.

Earlier: Libertarian Candidate Currently In Contempt Of Court Spotlighted

During his gubernatorial campaign nearly four years ago, which ended with him finishing in fourth among four candidates, Jackson said his divorce proceedings were what inspired him to run. The 20-year veteran of the Navy said he was often mislabeled as a father's rights activist.

Jackson, who was being held in civil contempt of court at the time, was sharply critical of Lake County judges during his bid for governor. During the campaign, he accused one of the judges he is charged with threatening to kill of politically motivated misconduct linked to his candidacy.

Update: Jackson's bail was increased at his Jan. 28 bond hearing. It will take $100,000 cash for him to secure his pre-trial release. If he posts the money, he was ordered to be placed under house arrest with GPS monitoring, to turn over his passport and to remain in Illinois and to have no contact with the two judges who he is accused of intimidating, among other things, according to the sheriff's office. He is due back in court via Zoom on Feb. 17.