It probably won’t surprise you to learn that Matthew Rupert, the Galesburg man accused of rioting and looting in Chicago and in Minneapolis after George Floyd was killed, has had previous brushes with the law.
Rupert — who allegedly posted cellphone videos of his activities on Facebook, including a “Let’s start a riot” admonition to protesters — has been arrested 44 times in his hometown alone. Rupert, who turned 28 last month, has spent well over a year in the Knox County Jail.
Most of Rupert’s arrests have been over acts of hooliganism, though there were some gun crimes as well, one of which landed him in an Illinois Department of Corrections boot camp.
That doesn’t count the seven times Rupert was arrested in the nearby community of Abingdon, where earlier this year he caught a felony meth possession charge that’s still in court.
Rupert had been living in Abingdon with a girlfriend. But she got an order of protection against him in December, and he moved back home with his mother.
The ex-girlfriend in Abingdon should not be confused with the girlfriend who was with Rupert in Chicago when he was arrested early this past Sunday. The young Hispanic woman was detained but not charged.
Together only a few months, she and Rupert recently got tattoos with each other’s name. The girlfriend has a job. He doesn’t but sometimes does seasonal work for a power-washing company.
Then, there’s another ex-girlfriend, the mother of a child Rupert raised as his own until a DNA test revealed he wasn’t the father.
Since federal charges against Rupert were revealed Monday, there’s been rampant speculation on social media about his motivation for joining the protests — with possibilities running the gamut, depending on the political bias of the accuser, from him being a white supremacist provocateur to an anarchist associated with Antifa.
Those most familiar with Rupert and his older brother Christopher, 29, who also was arrested in Chicago last Sunday, suggest the truth is far more mundane.
The Ruperts’ defining attribute, they say, is contempt for the police, with whom the family has had a contentious relationship for many years.
“They’ve just been very anti-law enforcement,” said Russell Idle, Galesburg’s police chief. “They’re very hostile toward law enforcement, very expressive of that.”
The Ruperts and the police have seen a lot of each other. Christopher Rupert, who goes by “Bubba,” has been arrested 20 times in Galesburg, a town of 32,000 in west-central Illinois, and has served four years in prison.
In the past five years, Matthew and Christopher Rupert each has been charged with threatening a public official over their alleged abusive treatment of police.
Christopher Rupert’s court case on that is pending.
Idle said that in addition to resisting arrest and threatening a police officer, Christopher Rupert threatened the officer’s family.
In an interview, Christopher Rupert said he would never threaten anyone’s family and complained that the police have long harassed him and his brother.
“My brother is a great kid,” said Christopher Rupert, who is due in court in Chicago July 17 to face a charge of reckless conduct. “People are making out like he’s some terrorist or something.”
One source of conflict with the police over the years has been what Idle described as the family’s malicious use of fireworks — sometimes to harass neighbors.
A major element of the case against Matthew Rupert involves accusations he was passing out explosives, calling them “bombs,” and encouraging others to throw them at police officers in Minneapolis.
Christopher Rupert, who denies having been in Minneapolis with his brother, said Matthew had no bombs, just fireworks, though he allows that they were big fireworks.
Kristy Rupert, 34, the oldest of five Rupert children, said her brothers just “love lighting off fireworks. They’re like 12-year-old kids in a 20-something-year-old body.”
Kristy Rupert said setting off fireworks has gotten her in trouble, too.
“We’re just idiots, I guess,” she said.
On the day that federal agents charged Matthew Rupert, they served a search warrant on the family’s Galesburg home, looking for explosives. Family members said they seized a cache of fireworks legally purchased in Missouri.
Matthew Rupert’s siblings said he has been misjudged by people drawing conclusions from the sensational accusations against him and from what they’ve seen on Facebook.
Instead, they paint a picture of an essentially good-hearted young man who had a rough upbringing, with a father who drank heavily and suffered from bipolar disorder. Rupert has always worked hard to support his mother, according to them, though they are vague about his source of income.
“Matthew really is a good guy when he’s not doing stupid sh—,” said his sister.
Others see Rupert, who has taken to calling himself Ricco, as a hapless, yet dangerous, wannabe gangster.
Knox County court records trace his interactions with the police to 2006, when he was picked up for truancy at 14.
Rupert did not complete high school, though he says on Facebook he has a GED. His brother and sister said he suffered from ADHD and struggled in school. His brother said it probably didn’t help that they started smoking weed at a young age.
The “El Ricco Rupert” Facebook page on which federal authorities said the incriminating videos were posted has been removed, but several other Facebook pages that Rupert maintained are still online. They are replete with photos of his tats, his sister’s pit bulls, his best buds (the green kind), fight-porn videos and posts about his love life and suicidal thoughts.
On Inauguration Day in 2017, Rupert taunted: “Happy Trump day bitches: Mexico will build that wall!!!”
When called out by friends on that, he said he was just playing around. “Trump is my president but I’m not racist,” he wrote.
Black Galesburg residents have engaged in lively Facebook discussions on that question. Detractors have noted he’s used the N-word hatefully in social media posts. Ohers have defended him, saying he’s not like that.
Though some who have reviewed the riot videos pointed out that he never mentions George Floyd, his brother and sister said he truly was upset about Floyd’s death — so upset that he made protest signs and posted them around Galesburg, until they were removed by police.
The police chief confirmed the appearance of signs with messages like “F… the Police” and “Police Kill.” He said he didn’t know who posted them but acknowledged Rupert would have topped a list of likely suspects.
The police removed the signs only because they were posted on utility poles, he said.
Kristy Rupert said her brother has friends of “all colors” in the racially diverse town.
Christopher Rupert choked up when he pointed out that Matthew has an African American nephew.
The accusations against Rupert certainly place him in the category of outside agitator.
But, for a final word, we’ll turn to Paul Cates, Abingdon’s police chief:
“He is no criminal mastermind, that’s for sure.”
