Out of prison, 'Alexander the Great' makes most of his second chance

Denning re-invents himself again: As a TikTok and YouTube phenom.

Alexander Denning works on a TikTok video outside the Olmsted County Government Center Wednesday, June 2, 2021. (Ken Klotzbach /
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ROCHESTER, Minn. — Alexander Denning was outside the Olmsted County Government Center last week making a TikTok video he was certain would push him across the 1 million followers threshold.

Known by his legion of fans as the self-styled Alexander the Great, Denning, 29, of St. Charles, was standing on the bridge spanning the Zumbro River with his wife and 3-month-old son. The scene was a measure as to how far his life had come in the last decade.

In the bright morning sunlight, Denning pointed behind him to the jail in the county facility.

Ten years ago, the jail was home for Denning, who faced first- and second-degree attempted murder and first- and second-degree assault charges stemming from a stabbing incident.

Looking out the jail window about midnight, Denning would see his mom drive by and flash the car's high beams. It was her way of saying good night.


Denning was heading to prison. He had reached a plea deal for 98 months in prison for first-degree assault. The prosecutor and the family of the victim wanted him to spend time in prison. Denning's attorney, who had taken the case pro bono after seeing it in the news, prepared him for prison, giving him a one in 10 chance of avoiding it.

But remarkably, the judge showed leniency and gave him 20 years of supervised probation. His lawyer was so overcome with emotion that he cried.


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♬ Steven Universe - L.Dre

Denning has always had a bit of a charmed life, but in this instance, his charm may have worked against him. Denning was caught in a robbery afterward and found to possess a gun. He was sent to prison.

In their own subsequent evaluations, authorities assessed Denning's odds of re-offending as highly likely. They thought he was largely unreformable. In prison, Denning was caught with a nail file in his shirt pocket while passing through a metal detector. He was put in "the hole" — a form of solitary confinement — for two months.

Denning's actions and society's view of him appeared to have reached an intersection.

Surrounded by influences and surroundings that reinforced his worst instincts, Denning's life was less a trajectory than a flat line. It appeared to have reached a dead end. So it is oddly ironic how Denning's pivot to a new life began. It started with a mob enforcer named Tony Vincent Caracciolo.

At the time, Caracciolo was serving two life sentences in a Minnesota prison for several mob-related arsons and two murders. Caracciolo worked as a janitor in the prison, and was the first prison inmate Denning saw after getting out of the hole. Caracciolo took a liking to Denning. He saw his potential — in a good way, not a bad way.


Alexander Denning takes his three-month old son William from his wife Abigail Denning before making a TikTok video outside the Olmsted County Government Center Wednesday, June 2, 2021. (Ken Klotzbach /

"He would always say ... the charm, the looks, the confidence, the energy. He often quoted a Jimmy Fallon TV show segment where Jimmy described it as being a 'likable person' and how it can take you far in life," Denning recalled. "He always brought it up. He said that's why he felt compelled to be my mentor and help me be a better person."

It was Caracciolo who told Denning to enter a prison Christianity program. It led to Denning becoming a Christian. It was Caracciolo who told Denning to become a model, something Denning had never considered.

After six years of prison life, Denning walked out of the Minnesota Correctional Facility-Lino Lakes a free man.

And he became a model.

Not that the doors just flung open. There were rejections from modeling agencies who were turned off by his many body-covering tattoos. But then he began to hit pay dirt. Modeling agencies saw what the mobster had seen: Looks, energy, personality and a towering pompadour. He was eventually hitting the modeling runway in New York, California and Chicago, while going to school at Rochester Community and Technical College.

Denning wasn't getting rich from modeling or acting. He also worked as a waiter at the Hilton steakhouse in downtown Rochester, but it was a far cry from prison life.


And when the pandemic hit and modeling gigs dried up, Denning began to pour his energy into TikTok and other social media platforms.

It was his third TikTok that blew up. Denning did a short video about how he would look out the window in jail, waiting for his mom to flash the high beams. The video got 5 million views on TikTok and 20 million on YouTube.

"I think modeling just propelled me. I don't think I'd be that interesting had I not gotten out of prison and been a model," Denning said. "It just blew up faster than I ever would imagine."

When a creator gets close to a million social media followers, it's not clear who is in charge. Making videos for TikTok and YouTube is a full-time job. Denning is part of TikTok's Creator Fund, allowing him to make money based on a combination of factors, including the number of views, the authenticity of those views, and the level of engagement on the content.

"I wake up and film videos all day, every day. I don't come off livestream," he said.

Denning agreed to color his distinctive pompadour a lavender after he reached 800,000 followers. If he reaches a million, he has pledged to dive into a pond and retrieve the weapon that was used in the incident that sent him to prison.

A recent monthly check Denning received from TikTok was for $1,200. But it's just one stream of revenue that Denning has created based on his videos and the marketing of his personality and life. He has his own clothing brand. He makes money off Instagram as well as when he's livestreaming.

"When you're living-streaming, people just send you money. It's odd. They just send you money," Denning said.

It's his videos about prison life that fascinate his followers and get the most views. He gets asked about the stabbing incident. He gets asked whether he's ever tried to get a hold of his victim, who was then 25.

The incident happened in the early hours of June 18, 2011. It was sparked when someone in Denning's car — either Denning or the driver — yelled an obscenity at the victim as he was riding his bicycle on a country road.

The man got into a car and pursued Denning's vehicle. The driver of the car said that the victim came speeding up behind him and tried to run him off the road a few times before both cars stopped. The victim said he approached the passenger side of the car to ask what the problem was. The driver said the victim charged at him and Denning.

In the altercation that followed, Denning stabbed the man in the stomach, forearm and back with a folding knife, then slashed the victim's tires.

Alexander Denning works on a TikTok video outside the Olmsted County Government Center Wednesday, June 2, 2021 with his brother, Christopher Denning, right. (Ken Klotzbach /

Asked if he is remorseful about the incident, Denning said he feels bad about how the situation turned out.

"I feel remorseful for the situation and how it panned out," Denning said. "I wish we both would have had different choices and how we handled it."

Denning said that while in prison, he used what is called the Minnesota Apology Letter Bank. He wrote a letter to the victim, but it's unclear whether the victim ever received it.

Denning said the letter he wrote was similar to what he said to the victim in the courtroom when he was being sentenced.

"I broke down. I was crying. 'Listen, I'm terribly sorry,'" said Denning, who recalled how the victim in court said his son would ask him how he got his scars. "It's an unfortunate circumstance that happened to anybody. I reacted wrong. And I feel like he reacted wrong, and it created chaos.

"I don't want to ever put somebody in a bad mood, a bad idea of who I am. Everything I do, I try to let people know: I'm not here for anything bad. I'm not here to start crap. I want to be friends with everybody."

In the comment sections of his videos, critics sometimes ask Denning's followers why they are "praising this criminal," Denning said.

"'I tried to comment back. Nobody's praising me for going to prison. They're praising the fact that I did not go back," Denning said.

But Denning also believes that if he hadn't gone through what he went through, he wouldn't be the person he is today.

"I don't think I'd be alive," Denning said. "I think my life was on a trajectory where I did whatever I wanted. I had no foundation in what I believed in, no morals. I would do anything and everything I wanted. Now, I still do that. But I have respect. And I have boundaries. And I do what's good."

Alexander Denning holds his three-month old son William before making a TikTok video outside the Olmsted County Government Center Wednesday, June 2, 2021. (Ken Klotzbach /

Alexander Denning holds his three-month old son William before making a TikTok video outside the Olmsted County Government Center Wednesday, June 2, 2021. (Ken Klotzbach /

Related Topics: PEOPLE
Matthew Stolle has been a Post Bulletin reporter since 2000 and covered many of the beats that make up a newsroom. In his first several years, he covered K-12 education and higher education in Rochester before shifting to politics. He has also been a features writer. Today, Matt jumps from beat to beat, depending on what his editor and the Rochester area are producing in terms of news. Readers can reach Matthew at 507-281-7415 or
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