“I didn’t get any sense she was in the Young Republicans,” her boss after college, Glenn Crawford, said. Now a divorce mediator, back then Crawford ran the Pasadena IT firm where Pushaw worked as a talent recruiter for a year after she graduated college. A Black liberal who openly talks about how “America was built on the back of slavery,” Crawford thought he would have picked up on any conservative vibes. He remembered her fondly as “businesslike, very proper, graceful, and composed for a young person.”

In September 2013, a year after the Reagan Library speech, Pushaw quit the IT firm and moved to Georgia.
Ostensibly, she was going to join one of Saakashvili’s big-vision projects: a Peace Corps-like government program to deploy thousands of English teachers, many of them Americans, into rural villages. The government recruited a wide range of people, including avid travelers with little teaching experience. Daryl Fernandez, a fellow teacher who went on to help run the program, said he gathered the idea was less to teach Georgians English than to do a little benevolent brainwashing, acclimatizing rural, traditional families to the coolness of the West.

But almost immediately after arriving, Pushaw appeared to acquire a life in Georgia that was different from other young American expats. She had connections to highly placed people that struck others as unusual. Other English teachers recall that she lived in a luxe apartment in one of Tbilisi’s fanciest neighborhoods, and very soon she acquired a job with a private company that helped Georgian students get into universities abroad.

In the early 2010s, American expats in Tbilisi liked to hang out at Betsy’s Hotel, the Tbilisi Marriott or the café in an English-language bookstore downtown. People who met Pushaw there and swapped messages with her on an expat e-mail group got the impression she aspired to become an establishmentarian foreign-policy analyst, a relatively centrist think-tank type. Several said her interest in foreign policy and in helping Georgia seemed truly sincere; one showed me an email where she asked for leads about shelters and veterinary clinics that could help neglected dogs living on the streets of Tbilisi.

But she began to cut a mysterious figure in the capital as a Gatsbyesque character who seemed to come out of nowhere but had a knack for presenting herself to extraordinarily influential Georgians as a desirable friend. Another American expat was surprised to open an email from Pushaw seeking an English tutor on behalf of a “very influential family here in Tbilisi.”

In late 2013, shortly after Pushaw arrived in Georgia, Neal Zupančič, an English teacher whom she met through the government teaching program, helped her create a website for an educational NGO she said she wanted to start. He was startled when he saw the intended co-founders were Giorgi Arveladze — a former presidential press secretary and minister of economic development
sometimes described as
Saakashvili’s “right-hand man” — and Georgia’s current deputy minister of agriculture.

Pushaw told Zupančič she’d gotten to know Arveladze by messaging him on LinkedIn. Zupančič found this plausible, because by the time Pushaw arrived in Georgia, Saakashvili and his friends were mounting an increasingly desperate search for supporters. (Arveladze did not respond to multiple requests for an interview.)

Some people in her orbit were beginning to wonder if Pushaw secured these connections because she had a direct line to Saakashvili. The resume she submitted to DeSantis to get a job with his team said she started formally working for Saakashvili in late 2017, first as a part-time consultant. (The Tampa Bay Times and the Miami Herald
acquired the resume in a public records request.) But
she said on RealPolitik, the Georgian TV show, that she knew Saakashvili before she moved to Tbilisi. And two people who spent time with Pushaw regularly in 2013 and 2014, both granted anonymity to speak freely, recalled Pushaw saying she and Saakashvili went on trips together. One said Pushaw claimed that she had flown to Batumi, a Georgian city on the Black Sea coast, and Greece with the ex-president.

Grant Freeman, a restaurateur and teacher who still lives in Tbilisi, said that he met Pushaw at a hookah bar in 2013 with a group of English teachers. At the bar, he said, she began showing him cell-phone selfies with a man he immediately recognized as Saakashvili. “I’ve just been in the botanical garden in Batumi” with Saakashvili, Freeman recalled her saying.

Some people who knew Pushaw in that time period also remember her telling them stories about her background that turned out to be fabricated, seemingly to present herself as closely entwined with the region. In mid-2015, Pushaw left her job at the Tbilisi college-counseling company to pursue a two-year master’s degree in international relations at the Johns Hopkins School of Advanced International Studies. A Johns Hopkins student said that Pushaw told her that she had been born in Eastern Europe and was adopted by an American couple.