At the Republican National Convention in Milwaukee last July, speakers fired up the crowd with pledges to cut taxes, secure the border, and push back against “woke” ideology.
Just a few blocks from the convention stage, 45 Republican donors, political operatives, and leaders sat down for dinner over steak and drinks. Among them were former Speaker of the House Kevin McCarthy, Donald Trump Jr., Tucker Carlson, and Joe Popolo Jr., BC ’89.
Popolo, an investor and business executive, found himself in Trump’s orbit once again. While he often crossed paths with Trump’s inner circle, Popolo said the experience still struck him.
“That dinner was an amazing experience,” Popolo wrote in a statement to The Heights. “Having spent more than a bit of time in Washington, it is refreshing to me to see someone who really wants to make this country better and does not need the money or is not worried about the next rung on the ladder.”
Just months later, Popolo himself would emerge into the political spotlight.
Earlier this month, Trump tapped him as the next ambassador to the Netherlands—a high-profile appointment, underscoring Popolo’s years of influence in Washington and his extensive connections across business and politics.
As this prominent Boston College alum takes the world stage, The Heights analyzed Federal Election Commission (FEC) filings, explored past and present business endeavors, and interviewed Popolo to contextualize a career that has positioned him to serve his nation in the Netherlands.
As an intern for his local representative, Popolo walked the same Capitol halls where he is set to be confirmed as ambassador in a few weeks.
A finance major at BC, Popolo said he always had an interest in politics. After graduation, he moved to Washington and waited tables at night to pay the bills during his unpaid internship.
Popolo landed a job at the national trade association for the trucking industry. The work was not glamorous—taking notes, writing speeches, and running errands. But it proved to be an invaluable learning experience, he said.
After a year, he considered applying to law school but decided against it. Instead, he accepted a job managing state government lobbying and outreach efforts for Roadway Services LLC., a trade association representing large trucking companies.
Popolo said the job taught him a lot. He developed connections with lawmakers and saw the inner workings of government up close. Ultimately, though, he gravitated toward business instead of politics.
Popolo earned his MBA from the University of Chicago Booth School of Business in 1997 and went to work at the Freeman Company, an event management company providing services for trade shows, exhibits, and other corporate events.
His wife, Christine Freeman-Popolo, and her family owned the company, which was founded by her grandfather in 1927. Popolo was hired as the assistant treasurer, quickly rising through the ranks to become the president and CEO.
“It turns out that hard work, dedication and marrying the Chairman’s daughter is good for your career trajectory!” Popolo wrote.
During his eight years as president and 11 as CEO, the company’s revenue grew from $700 million to over $3 billion, according to Popolo. It also expanded into the UK, China, and other global markets.
Amid the fallout of the 2008 financial crisis, Popolo guided Freeman through the acquisition of an audio-visual services provider for hotels. The division, Encore Global, was later bundled with five other companies and sold to private equity giant Blackstone Inc. in 2019.
The terms of the deal were not made public. Following the sale, Popolo stepped down as CEO.
“It was a great transaction for the family,” Popolo wrote. “It allowed me to turn the reins over after 22 years and set up our family office.”
Later that year, Popolo founded his own investment firm, Charles & Potomac Capital LLC (C&P). The firm focuses on private equity and venture capital investments, while also directly investing in and advising select companies, according to Popolo.
“My lens at C&P is to find smart people with good businesses and try to help make them better,” Popolo wrote. “I am not as much focused on particular sectors as I am finding people I trust who are smarter than me and investing alongside of them.”
Aside from his work at C&P, Popolo is a patron of the arts at the Vatican Museums and regularly contributes to various Catholic charities. He was elected to the BC Board of Trustees last year and endowed the executive directorship of the Shea Center for Entrepreneurship.
He also helped found Friends of the Heights, a name, image, and likeness collective for BC athletes that allows student-athletes to participate in business opportunities and charitable causes. Last year alone, the collective shared on LinkedIn that it had raised more than $2.4 million.
In 2003, Popolo began consistently donating to the Republican Party.
According to FEC filings reviewed by The Heights, Popolo made his first political contribution in March of that year—a modest $500 donation to a Republican-affiliated Political Action Committee (PAC). Less than 20 years later, his campaign-cycle donations would tally in the millions.
At the time of his first donation, Popolo had assumed his role as a board member at the Freeman Company less than two years prior. Motivated by a sense of gratitude for what he had achieved and guided by his Catholic faith, Popolo said he began supporting the Republican Party as a way to give back.
“I sincerely believe that political and economic freedom, personal responsibility, individual liberty, access to a great education and a limited government are the best combination of ingredients to make that happen,” Popolo wrote. “So I put my resources behind the Republican Party because I believe that is the best way to live out my Catholic values.”
Throughout the 2016 presidential cycle, Popolo was a significant GOP donor. It was also during this time Popolo said he began to support Trump.
“I supported [Trump] in 2016 and then in 2020,” Popolo wrote. “I sincerely appreciate his love for this country and for his desire to provide our citizens with the greatest amount of freedom and opportunity.”
But at the beginning of the 2016 presidential primary, FEC records show Popolo initially supported Texas Senator Ted Cruz’s presidential bid over Trump’s. He made several contributions to Cruz’s campaign during the primary season.
It was only after it became apparent Trump would be the Republican nominee that Popolo signaled his support, making his first donation to Trump in June 2016.
Although he ultimately chose to support Trump, Popolo’s support for his campaign was relatively modest compared to his contributions to Mitt Romney in the previous presidential race.
During Trump’s tight 2016 contest against Hillary Clinton—where he secured narrow victories in the must-win states of Wisconsin, Michigan, and Pennsylvania by less than 1 percentage point—Popolo only donated $3,700 directly to the Trump Victory PAC.
Nevertheless, Popolo contributed over $141,300 to other Republican-affiliated groups and candidates throughout the 2016 cycle.
In 2020, Popolo doubled down on his support for Trump.
According to FEC individual contributions data, Popolo donated a combined total of over $1 million to Trump’s campaign, Republican candidates, Republican-affiliated PACs, and conservative Super PACs. This amount was seven times greater than his contributions during the previous presidential election cycle.
Among other significant contributions in 2020, Popolo donated $150,000 to the Senate Leadership Fund, which sought to maintain and expand a Republican majority in the Senate, according to its website.
The largest total amount Popolo contributed to a single entity in 2020 was $232,500, directed to the Trump Victory PAC through a combination of contributions.
Popolo’s steadfast support for Trump noticeably wavered during the 2024 GOP primary season, as Popolo diversified his donations between various candidates and candidate-affiliated PACs.
Four days after Florida Governor Ron DeSantis announced his presidential bid in May 2023, Popolo donated $100,000 to a DeSantis-affiliated Super PAC. In total, Popolo’s donations to the DeSantis camp exceeded $200,000.
Although Popolo confirmed to The Heights he initially supported DeSantis to become the GOP nominee, in December 2023, Popolo also donated $150,000 to Americans for Prosperity, which had endorsed Nikki Haley’s candidacy just a month prior.
Once again, similar to 2016, as Trump solidified his lead in the GOP primary—polling 18 and 19 points ahead of Haley, the only remaining candidate by the end of January—Popolo decided to lend his support to Trump.
By October 2024, Popolo had donated a staggering $827,900 to the Trump campaign—nearly matching his contribution total for the 2020 cycle.
In addition to his contributions to Trump and Republican-affiliated organizations, Popolo donated $150,000 to pro-voucher, pro-school-choice groups. The largest share went to the School Freedom Fund, which states on its website that children’s education has been hindered by policies like mask mandates and critical race theory.
In total, Popolo’s donations to Republican candidates, conservative-affiliated PACs, and Super PACs in the 2024 election cycle amounted to $2,971,408.87, according to contribution data reviewed by The Heights.
While Popolo was active in the political arena through donations, he also expanded his influence in the business sector.
Popolo began investing in Ondas Holdings Inc., a company owned by one of Popolo’s classmates from his time at UChicago, Eric Brock. According to Popolo, shortly after his initial investment in 2020, he led an investor group that took a “meaningful” stake in Ondas Networks Inc., a major subsidiary of the company.
In 2022, while Popolo was amassing his stake in the company, Ondas began the acquisition of Airobotics LTD, an Israeli defense company specializing in autonomous counter-drone systems, which developed a system called Iron Drone Raider.
According to American Robotics—the Ondas subsidiary that now manages Iron Drone Raider—the drone system is designed to detect, track, and intercept hostile unmanned aerial vehicles, and may be used in civil or combat settings.
In April 2024, after obtaining a 19 percent beneficial ownership of Ondas Holdings, Popolo was appointed to its board of directors.
The following month, Ondas announced it had secured an initial purchase order from an Israeli defense company for the Iron Drone Raider System.
In July, Ondas announced another purchase order for the raider system intended to be deployed as “part of military defense activities to protect from hostile drones threatening borders, critical locations, populations, and defense forces.”
By the end of the third fiscal quarter of 2024, Ondas reported securing multiple military orders totaling $14.4 million for Iron Drone Raider from “a major military customer.”
Following an investigation into war crimes and crimes against humanity allegedly committed by Israeli Prime Minister Benjamin Netanyahu and former Minister of Defense Yoav Gallant during the Israel-Hamas war, the International Criminal Court (ICC) issued arrest warrants for their alleged involvement.
The ICC is an international tribunal based in the Netherlands, where Popolo is expected to become the American ambassador.
In response to a question posed by The Heights about a potential conflict of interest relating to Israel, Popolo acknowledged that his role on the board of Ondas could create a potential conflict when he assumes the position of ambassador.
“The [Office of Government Ethics] will give me guidance,” he wrote.
After the election last November, Popolo had all but decided to decline offers to serve in Trump’s second administration, instead opting to continue managing C&P.
Last month, though, Popolo got a call from the Trump transition team asking if he would be interested in being nominated as an ambassador, with a choice of five countries.
Without missing a beat, he decided to accept the ambassadorship to the Netherlands.
“It is a tremendous honor to be asked to serve our country and the Netherlands is a great ally and a very important national security partner,” Popolo wrote.“At Freeman our European entities all rolled up into a company in the Netherlands so I have had the opportunity to travel there and meet some tremendous people. Our two nations have a great relationship, and if I am confirmed I hope to build on that.”
Popolo is one of over three dozen political nominees who donated to Trump’s campaign, according to a CNN analysis. His appointment continues a long, bipartisan trend of major donors being given ambassadorships under the candidates they supported.
Like all ambassadors, Popolo’s appointment is pending approval by the Senate Foreign Relations Committee. A tentative date has not yet been set for his hearing, a spokesperson said.
According to Popolo, ambassadors must reside in their countries for all but 28 working days each year. He will be tasked with managing roughly 400 State Department employees across multiple locations, so he will give up the day-to-day management of his investment portfolio, he said.
In addition, he will be required to disclose any potential conflicts of interest to the Office of Government Ethics and, based on their guidance, may need to divest from certain companies.
The U.S. Embassy at The Hague did not respond to a request for comment.
Popolo’s career continues to span government and business, but his long-term ambitions lie elsewhere.
Eventually, he said he hopes to pursue philanthropy full time, dedicating his time and resources to the causes he and his wife find most important.
“Chris and I have been so blessed, and we both feel called to serve,” Popolo wrote. “We are passionate about improving education outcomes, helping people get back on their feet and supporting great organizations that align with our respective faiths.”
Editor’s Note: Contribution records were cross-checked based on all known variants of Popolo’s name and against publicly available employer data. Federal election laws require donors to truthfully disclose their occupation and employer.
Federal law also requires the disclosure of political spending that exceeds $200 on a single candidate within an election cycle. The data does not include contributions made to independent expenditure campaigns, super PACs, or nonprofit groups organized under section 501(c)(4) of the tax code, which engage in electioneering communications.
The total figure for the 2024 election cycle includes all public contributions Popolo made between Jan. 1, 2023, and Dec. 31, 2024. FEC data is updated quarterly.
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