Charlie Kirk, known for his conservative stance, grew up as a unique voice in the predominantly Democratic suburbs of northern Chicago. Despite his influence, his younger sister Mary eventually shifted her support, transitioning from backing her brother to becoming an enthusiastic supporter of left-wing Bernie Sanders.

Mary Kirk, now 29, maintains a low profile and uses a pseudonym on Facebook, leading to some misconceptions in online articles that describe Charlie as an only child. Back in 2011, she was part of the Wheeling (Illinois) Young Republicans.

That was the year before her brother and his mentor Bill Montgomery founded what would become the powerhouse Turning Point USA.

During his high school years in the northern suburbs of Chicago, Charlie led the Wheeling Young Republicans, fostering conservative principles. However, Mary’s political alignment began to change after she encountered Vermont Senator Bernie Sanders during his inaugural presidential campaign in 2015.

‘#tbt to when I met Bernie a year ago and had no idea who he was and now he is the light of my life’, Mary captioned a social media post of her grinning and shaking hands with Sanders a second time in 2016.

Later that year, she shared a photo of Sanders at a podium on the campaign trail facing a small bird that had perched itself on the lectern.

‘I was the bird,’ Mary wrote.

Close friends of Charlie, who was assassinated on September 10 in Utah at age 31, are tight-lipped about Mary’s swing to the left but most say it did not result in a family rift.

‘Mary was a devoted sister to Charlie,’ Mike Miller, a suburban Chicago jeweler who first gave Turning Point a $50,000 donation in 2014 and is now on TPUSA’s board of directors, told the Daily Mail. ‘Her politics are her business.’

Miller, who lives a few miles from the Kirk family home in Prospect Heights, has known the entire family for years even though he admitted he hasn’t seen Mary for five years.

Mary Kirk did not immediately return Daily Mail’s request for comment. 

Charlie’s parents, Robert Kirk, 73, an architect, and Kathryn Kirk, 68, a mental health counselor, guard their privacy and the neighbors at their stately home at the end of a cul-de-sac are so protective that neighbors call the police when reporters come by.

‘Their family was no different than a lot of families these days,’ another friend who did want to be named said.

‘Charlie went one way, Mary ending up going the other. Their parents are pretty moderate conservatives.’

‘They’re strong-willed, very grounded, very humble people,’ multi-millionaire paving tycoon Gary Rabine, who met Charlie when he was just 18 and became a financial backer, told the Daily Mail about Charlie’s parents.

‘They’re not lightweights by any means, but they’re not political junkies either.’

Charlie was fine with it if even a close relative like Mary did not see eye to eye with him, Rabine said.

‘He loved having those debates, even with family,’ Rabine said. ‘He didn’t disown anyone, and they didn’t disown him. That’s the example we should follow.’

Mary graduated from the University of Illinois at Chicago in 2019 with a degree in art history, criticism and conservation, and works both as a gallery assistant and runs her own art collection consulting business, Kirk Art Services.

Her social media includes some left-wing sounding tropes more in tune with some of Kirk’s opponents — such as one post showing a woman grimacing at a man which she captioned: ‘mood towards patriarchy’.

A few months ago she encouraged people to support the Whitney Plantation, a New Orleans museum that educates the public about the history and legacies of slavery in the US but has had its funding revoked by the Trump Administration.

‘Whitney Plantation is an inspiring example of what slavery education should look like in the US. Please support if you can!’ Mary wrote on LinkedIn.

But Charlie’s friends, many of whom date back to his middle and high school days, say he never let anything or anyone – certainly not his sister or classmates at Wheeling High who looked down on him – distract him from building Turning Point USA into the political and media juggernaut that made him a millionaire when he was still in his 20s.

Maybe that was because he had a secret weapon: his Chicago Cubs-loving grandmother Patricia Smith aka ‘Gram’ on her many Facebook posts, who died in 2019 at the age of 96.

‘She might have been his biggest supporter,’ Mike Miller said. ‘She was an amazing woman and devoted to Charlie.’

Peter Christos, who recently left TPUSA after three years on staff, first met Charlie in 2020 at a student leadership conference in West Palm Beach, Florida when Christos was a high school senior.

Christos, who grew up in the Chicago suburbs like Charlie, said it wasn’t easy to be an outspoken conservative in that environment.

‘It’s very tough,’ he said. ‘You face pushback from your employer, online harassment, even physical violence. That’s why so many people stay silent. 

‘There are crazy people who will attack or kill you just for having a different opinion. And that’s what happened to Charlie.’

Still, Charlie was captain of the high school basketball team and played varsity football as well – all the while challenging teachers he felt were too Marxist.

‘I think people liked him even if they didn’t agree with his ideas because he was super humble when he could have been cocky,’ Christos said.

‘He was brilliant without going to Harvard or Princeton. He loved God, loved his family, loved his country. And he centered his life around his faith. That’s what inspired me to get involved.’

Charlie had already relocated to Phoenix, where he lived with his wife and two children at the time of his death, by the time Christos got involved with TPUSA.

‘But even though he wasn’t living here anymore, his heart was always in Illinois,’ Christos said.

Christos was leading a Turning Point anti-mask mandate initiative at Glenbrook North High School in 202s when he says he was assaulted by a pro-Palestinian protester.

Charlie immediately flew to Illinois to support him. ‘He did a rally with me and Tom DeVore in St. Charles at the Arcada Theatre,’ Christos recalled. 

‘That just showed how committed he was to defending students and their rights. He was always in our corner.’

That loyalty extended to gay men, said Ecan Draim, who met Kirk in late 2011 when he was not quite 17 and they were both involved in local Republican politics.

‘He was unbelievably loyal to all his friends,’ Draim said. ‘There was one CPAC meeting where he was holding court with a lot of people and then giving an interview. 

‘He saw me and stopped his whole interview and talked me up. The people he was interviewing then wanted to interview me.’

Draim said the biggest misconception about Kirk was that he was a bigot. A lot of gay Republican men, Draim said, were involved with TPUSA at the highest levels.

‘I’m gay and Charlie was one of the first people I felt comfortable telling,’ Draim told the Daily Mail.

‘We had some disagreement about the policy issues but it didn’t change his opinion of me in any way and he was very supportive. It’s telling that he was one of the first people I felt comfortable to tell.’

Draim said that when he first heard the news that Kirk had been shot, he believed he was going to pull through.

‘I was in a very bad state, crying heavily, when I found out,’ Draim said. ‘I sent a text to Charlie’s cell phone number after he died.

‘I said, Rest in peace brother. We were two young kids with young dreams. And you changed the world.’