Jon Ossoff was 16 years old when he wrote a letter to John Lewis, the Georgia congressman and civil rights pioneer, that led to a spot as a volunteer in Mr. Lewis’s office.
When Mr. Ossoff was 19 and a rising sophomore at Georgetown, he went to work for Hank Johnson as the primary speechwriter and press aide for Mr. Johnson’s 2006 congressional campaign.
And Mr. Ossoff was 26 when, without any journalism experience other than an internship, he was made chief executive of a small documentary film company based in England.
Mr. Ossoff has always been adept at making his own breaks. He has consistently outperformed his professional résumé, impressing lawmakers many years his senior with his intellect and drive. And he has capitalized on his own well-off upbringing and a series of well-timed introductions and personal endorsements to rise through Democratic politics in Georgia.
Now 33, Mr. Ossoff is pursuing his most ambitious goal yet: to capture a seat in the United States Senate against an incumbent Republican, David Perdue, in a traditionally conservative state. If successful, he would become the youngest senator in 40 years.
Mr. Ossoff first emerged on the national stage in 2017, when his bid for a House seat in a special election provided Democrats the first opportunity to express resistance to President Trump. Though he lost a close race in a well-off district in suburban Atlanta, the energy surrounding his candidacy enabled him to shatter fund-raising records and build the political network that has put him within reach of the Senate.
That energy has hardly abated. Federal filings made public last week showed Mr. Ossoff to be the best-funded Senate candidate in history after pulling in $106.7 million from mid-October to mid-December — almost $40 million more than Mr. Perdue’s tally. The stunning totals reflect the stakes: If Mr. Ossoff and the Rev. Raphael Warnock win their runoff races on Jan. 5, Democrats will gain control of the Senate.
Still, Mr. Ossoff has little record to run on, or against. Other than campaigning for positions in Congress, he has spent the years since leaving Mr. Johnson’s office running Insight TWI, an investigative documentary company of eight staff members that has headquarters in London — doing so mostly from Atlanta.
He has mounted a campaign based less on his own experience and accomplishments and more on the idea that his election will help foster a political change in Georgia — the kind voters signaled they wanted when they backed Joseph R. Biden Jr. in the presidential election. He has also consistently cited Mr. Perdue’s financial dealings to label him “a crook” who cashed in on the pandemic, an allegation Mr. Perdue denies.
At campaign events, Mr. Perdue, 71, often fails to even mention Mr. Ossoff as an opponent. Instead, he and Kelly Loeffler, the other Republican Senate candidate, direct most of their attacks at Mr. Warnock, whom they view as a more substantive target. Mr. Perdue skipped a debate against Mr. Ossoff early this month, leaving the Democrat onstage by himself making his pitch to voters, but he has unleashed an onslaught of negative ads against Mr. Ossoff, portraying him as a hostage of the radical left.
None of this has dented Mr. Ossoff’s confidence. As he heads into the final days of the race, he has emphasized his connections to Mr. Lewis. And far from apologizing for his youth, he has cast himself as the inheritor of the legacy of young people who have taken leadership roles in progressive political organizations in the South.
“John Lewis was 23, 24 years old when he was leading the Student Nonviolent Coordinating Committee,” Mr. Ossoff said during an interview last week. “I was so inspired by the fact that young people in that movement had made a difference. And I don’t think that young people should simply wait their turn but should engage fully in the life of our communities, and our country, and our world, and try to make a difference.”
Changing Politics in Georgia
When Mr. Ossoff began his first campaign for Congress in 2017, he initially ran his campaign headquarters out of the basement of his parents’ Atlanta home. When he was in Washington, he stayed at a Capitol Hill townhouse owned by his father.
At the time, Mr. Ossoff described himself as a former “senior national security staffer,” which was something of an embellishment considering that he had been a midlevel committee staff member for Mr. Johnson.
The Republican case against him boiled down to his not living in the district he sought to represent and an assertion that he would be a pawn of Nancy Pelosi, then the House minority leader.
“Other than being born to rich parents, Jon Ossoff has never accomplished a single thing in his life,” said Corry Bliss, who ran a Republican super PAC that spent millions attacking Mr. Ossoff in the 2017 race.
But Mr. Ossoff received a critical endorsement from Mr. Lewis, and he proved to be an adept fund-raiser who quickly built connections with key constituencies. Progressives rallied to him as a way to express their outrage at the Trump administration. In the runoff, Mr. Ossoff got 48 percent of the vote, losing to Karen Handel.
In the 2020 Senate race, Mr. Ossoff is running as a mainstream Democrat, expressing sympathy for but not aligning himself with the party’s most liberal figures. He has stayed on message, hammering Mr. Perdue over his finances, and perhaps more important, he has not made any major mistakes on the campaign trail or in interviews.
There has been very little reliable public polling of the two Georgia Senate runoff elections, but few doubt that Mr. Ossoff is facing an uphill climb. Georgia has not sent a Democrat to the Senate since 2000 and hasn’t elected any Democrat to statewide office since 2006. And Republicans have traditionally had an advantage in Georgia runoffs because the Democratic electorate includes people who vote more infrequently.
In the last Georgia Senate runoff, three weeks after the November 2008 election, voter turnout sank to 2.1 million from 3.7 million.
Georgia Democrats say much of that calculus has changed in 2020, as Stacey Abrams, who narrowly lost the 2018 race for governor, has built a permanent progressive campaign infrastructure in the state. Already, more than two million Georgians have voted in the 2020 Senate runoffs.
“There is no more conventional wisdom, period,” said Jason Carter, a grandson of former President Jimmy Carter who was Georgia Democrats’ candidate for governor in 2014. “This election is different, this moment in history is different, and whatever anybody thinks they know, they don’t.”
Impressing John Lewis
The son of a publishing executive and a management consultant, Mr. Ossoff attended the prestigious Paideia School in Atlanta. In 2003, he read Mr. Lewis’s biography and talked his way into a volunteer position in the congressman’s office the next summer.
Michaeleen Crowell, who worked as Mr. Lewis’s legislative director and overlapped with Mr. Ossoff, said the congressman had received hundreds of letters from ambitious young people and that a parade of interns had come through his office. Mr. Ossoff, she said, made a special connection with the civil rights leader.
“You remind me of another time in my own life,” Mr. Lewis said to Mr. Ossoff in an Ossoff campaign video posted to Facebook in April, before Mr. Lewis’s death in July. “When I was 17 years old growing up in rural Alabama, I wrote a letter to Dr. King, and he wrote me back and sent me a round-trip Greyhound bus ticket and invited me to come to Montgomery and meet with him. And it changed my life.”
In the spring of 2006, Ms. Crowell helped arrange Mr. Ossoff’s transfer to work for the campaign of Hank Johnson, who was running a primary campaign against Representative Cynthia McKinney.
“He came to me asking if I could connect him,” she said of Mr. Ossoff. “I knew the folks who were running Hank’s campaign. So I said: ‘I know this young kid. He’s a go-getter.’”
Mr. Ossoff had just finished his freshman year at Georgetown University and had never worked on a campaign before. But in an initial three-hour meeting, he pitched Mr. Johnson, a local politician with a small law office, on using the internet to communicate with Democratic primary voters as well as donors, reporters and bloggers elsewhere.
“He wanted to use blogs and this new thing that I’d never heard of, Facebook, and so I gave him license to do that,” Mr. Johnson said. “It immediately put my campaign on the map. It got my campaign national attention.”
Mr. Ossoff quickly became one of Mr. Johnson’s most trusted aides. Mr. Johnson dispatched him to talk with Daraka Satcher, who would go on to become the congressman’s first chief of staff.
The two met at Bullfeathers, a venerable watering hole steps from the Capitol. Mr. Satcher said he had seen “this kid standing outside” who smiled and opened the door for him.
“I was offended, because he was clearly this kid, and I was like, ‘Do they really send a kid to vet me out?’” recalled Mr. Satcher, who then was in his early 30s.
Nonetheless, they sat down at a table for about an hour and a half and talked. “I’ll tell you, by the end of that lunch I was so impressed with him and his knowledge about policy and politics and his insight that it made me want to help the campaign even more,” he recounted. “I went from being offended to overly impressed,” Mr. Satcher said.
Mr. Johnson went on to beat Ms. McKinney and won accolades for his tech-savvy campaign. National Journal wrote that Mr. Johnson’s campaign had “the most unique blog strategy” and quoted Mr. Ossoff saying that blogs were “effective in reaching out to the people who make the news, the people who determine what’s hot and what’s not.”
When Mr. Johnson went to Washington the next January, Mr. Ossoff split time between his Georgetown studies and a job as a legislative correspondent in Mr. Johnson’s Capitol office, a highly unusual arrangement for an undergraduate.
Like many other young congressional staffers, most of Mr. Ossoff’s time was spent writing news releases and floor speeches that would be viewed only by the most die-hard of C-SPAN viewers. But in Mr. Johnson’s sixth month in office, Mr. Ossoff had achieved what would become his most concrete accomplishment: He proposed and wrote a House resolution that Mr. Johnson sponsored calling for peace talks to solve a conflict in northern Uganda.
“He was concerned about children being manipulated and used in an atrocious way,” Mr. Johnson said. “I knew nothing about the conflict before he brought it to my attention, and once he did, I thought it was a great idea.”
While he was at Georgetown, Mr. Ossoff sang in the campus a cappella group. Later he earned a pilot’s license in his off hours.
From Politics to Documentaries
In 2003, Mr. Ossoff attended a small dinner party with his mother in southwestern France. At an outdoor table in a plum orchard, on a lovely summer evening, Mr. Ossoff was seated across the table from Ron McCullagh, a former BBC journalist who in 1991 had founded Insight News Television.
The company had produced award-winning documentaries such as “Cry Freetown,” about Sierra Leone’s civil war, and “Exodus,” which examined the efforts by thousands of Africans to make their way to Europe in search of better lives. Both films won Emmy Awards, among other prizes.
Mr. McCullagh and the teenage Jonathan Ossoff, as he called himself then, spoke for several hours, leading to a lasting friendship and a professional relationship.
“I was completely blown away by his brightness, by his intelligence and by his knowledge,” Mr. McCullagh recalled, adding how he had been struck by Mr. Ossoff’s “curiosity.”
“He told me about his thoughts on Chinese and American relationships, the importance of the China Sea” and the “strategic importance for the world of freedom of trade in that part of the world,” Mr. McCullagh recounted. “And the detail, knowledge he had of the situation was just very impressive. It was a very memorable dinner, and from that point on, we became friends.”
Mr. Ossoff ended up doing an internship at Insight News in July 2008. Five years later, Mr. McCullagh made a bold personnel move: He decided to hire Mr. Ossoff — then 26, with virtually no journalism experience — as chief executive of the organization and changed its name to Insight TWI — The World Investigates.
“It was a risk, but a calculated risk,” Mr. McCullagh said. “I wanted someone to take us forward. We needed some new thinking, and we got it.”
Mr. Ossoff invested $250,000 in Insight TWI months after he had joined, “to expand the business after Jon took over, when Jon came to Ron with some ideas,” according to a spokeswoman for Mr. Ossoff’s campaign. She said that Mr. Ossoff’s investment had not been related to his appointment as chief executive. Mr. McCullagh also invested the same amount at the time.
Mr. Ossoff’s campaign promotes him as an “investigative journalist,” though he does not act as an investigative reporter. As chief executive, he vets story ideas, helps prepare interview questions and attends to film production, editing and security arrangements for his staff. Mr. Ossoff also supervises the commissioning of documentaries with news media organizations like the BBC and Al Jazeera English.
According to his Senate campaign, Mr. Ossoff has been the executive producer of more than two dozen Insight TWI films on such subjects as soccer corruption in Ghana and child trafficking and sexual exploitation along the border of Bolivia and Argentina.
In Mr. Ossoff’s most recent personal financial report, filed in July, he valued Insight TWI at between $1 million and $5 million. According to records filed in November in Britain, he owns 75 percent or more of the organization’s shares.
Anas Aremeyaw Anas, a Ghanaian journalist who has worked with Insight TWI, said Mr. Ossoff had expanded the organization’s mission of having local reporters in Africa and other regions develop their own stories.
“The strategy was that we didn’t want parachute journalism,” Mr. Anas said. “Jon believed in having local journalists in places like Africa telling their stories and not having white men coming in.”
Diarmuid Jeffreys, manager of investigative programs for Al Jazeera English, called Mr. Ossoff a “tough negotiator” when it came to getting Insight TWI’s work commissioned.
“He doesn’t like to be pushed around,” Mr. Jeffreys said. “He will walk away if he doesn’t think a project is commercially viable or if he doesn’t think he can deliver it properly. He won’t just take any gig.”
Over the years, Insight TWI has prided itself on awards it has earned. Over a 14-year stretch beginning in 1999, according to its website, the company logged 47 awards or instances in which its documentaries were finalists, “shortlisted” or nominated for prizes. The awards include two Emmys, a Peabody and one British Academy of Film and Television Arts Award.
But there had been a drop-off in awards before Mr. Ossoff’s tenure at the helm, and in the eight years under his leadership, that has not changed; the company has received just two journalism prizes in that time.
“We have not prioritized applications for awards,” Mr. Ossoff said. “You can spend a lot of time applying for awards, and that time might be better spent developing journalism.”
Sheelagh McNeill, Susan Beachy and Kitty Bennett contributed research.