Not too long ago, when it came to dealing with Maduro & Co., Ric Grenell was considered a key figure in Washington DC. As the US braced for Trump’s second coming, Grenell was even deemed a contender to lead the State Department. The president opted for Marco Rubio, but created a new diplomatic post exclusively for Grenell: the Special Presidential Envoy for Special Missions, which had a Special focus on Venezuela and North Korea.
Given the leeway some middlemen retain in the Trump White House, Grenell’s debut was the subject of widespread speculation about who would ultimately command the Venezuela portfolio. Days into the second Trump presidency, while Maduro secured his last inauguration with an iron fist, Grenell arrived in Miraflores to meet with the dictator and his political strategist, Jorge Rodríguez, who looked delighted. Grenell left Caracas with six US citizens Maduro had held hostage, which he framed as a resounding diplomatic victory, though many more American prisoners were still left behind. He soon reaped a reward: Trump appointed Grenell to manage the Kennedy Center, an ideal hub to sow political and financial connections through grandiose social events. The president even wanted to rename the venue after himself. Grenell—widely considered a “MAGA insider”—emerged as an ideal ally to seal Trump’s imprint on the institution. It didn’t last long.
Twenty months later, he lost the job at the Kennedy Center and currently has no place in the current arrangement between Trump and Delcy Rodríguez.
Since last week, Grenell has been embroiled in a scandal of a multimillion-dollar, international dimension, which goes back to his Kennedy Center tenure. It speaks of the network of friends and contacts he had access to when empowered vis-à-vis the chavista clique. The New York Times characterizes the unfolding saga as “bitter even for Trump-era standards.” As it stands, the episode is yet another example of the broad discretion and opacity that US officials have claimed for themselves to navigate relations between Washington and political elites in Caracas, Balkan capitals, and beyond.
The Mildons and a misplaced transaction
The saga gained attention when news broke about the wedding between Trump’s former personal lawyer Alina Habba, 42, and Turhan Mildon, an obscure Turkish investor in his 20s with ties to President Recep Tayyip Erdogan. Mildon started to operate in Venezuela’s construction industry when Maduro was still in power, after a seemingly lucrative experience in the Democratic Republic of Congo. Love and business drew him to Caracas, the Middle East Eye reported in September: Mildon was then in a relationship with the daughter of Remigio Ceballos, a powerful chavista military commander, while he partnered with the Venezuelan State to revive as many as 10 unproductive cement plants.
His facilitator in Caracas was no other than Alex Saab, the disgraced moneyman of Maduro who is now in US custody.
According to New York Times reporters, Mildon not only lobbied Saab for the “Vencement” deal, but also took over a once-successful shrimp exporter Maduro seized in 2024. The company’s original owner is imprisoned in Venezuela.
Regarding Mildon’s new romance, he told the MEE that he met Habba some time ago through a mutual friend, “an ambassador in the US.”
Caption: All smiles between Habba and the special envoy in the early days of Trump’s second term. Source: Grenell’s Instagram account.
The public fallout between Habba and Grenell surfaced last week, involving allegations over political favors in exchange for a multi-million-dollar contribution that was never registered. Axios first reported that Habba stormed into the Oval Office to tell Trump that Grenell persuaded Mildon, her new husband, to wire a $17.6 million donation to the Kennedy Center last year via a third-party’s bank account. Grenell denied the allegation on the spot, challenging the Mildons to submit proof.
Caracas Chronicles reached out to Grenell’s camp for comment on these developments and any reflections on his work in Venezuela, including whether he remains in contact with government officials under Delcy. We haven’t received a response. A Venezuelan opposition source who closely monitors Alex Saab’s legal case and business dealings declined to comment at this stage.
On Monday, Axios gave us an idea of the kind of evidence that Mildon’s lawyers are handing over. Grenell reportedly texted Mildon that the transaction would secure access to US officials, maybe even the president himself, through “VIP events” at the Kennedy Center. Grenell also offered to make him “the American face down in V,” which sounds like he saw Mildon as a potential poster child for US business interests in Maduro’s Venezuela.
Axios reports that a private defence company called TXAT allegedly received the payment. The transfer would not come from Mildon’s bank account, but from an account linked to the Congolese Ministry of Finance.
While revelations pile up and the Mildons build their case before President Trump, Grenell keeps witnessing his own change of luck, which began in the second half of last year, with the US military deployment in the Caribbean, and continued with Maduro’s ousting on January 3.
A bad streak
“I understand what he [Maduro] wants. I believe we can still have a deal. I believe in diplomacy, I believe in avoiding war,” Grenell claimed on September 17, 2025, during the CPAC international conference in Asunción, Paraguay.
Grenell already looked out of the loop. It was the early days of a US military campaign a few kilometers away from Venezuela, which had the stated purpose of dismantling narco-trafficking networks in the region. Grenell had become a champion of a supposedly mutually beneficial cooperation with the chavista elite in previous months. In contrast with the likes of Rubio and Mauricio Claver-Carone, Grenell pushed for the normalization of relations between the Trump administration and the Maduro regime. He portrayed his in-person meeting with Maduro and Jorge Rodríguez as a sign of what his approach could achieve. Soon, the US began deporting Venezuelan migrants and detainees in charter flights to Maiquetía, which Grenell could publicize as proof that his plan was working.
Analysts and reporters speculated over which idea would prevail: Grenell’s pitch that working with Maduro was the safe bet, or Rubio’s insistence on revoking the Chevron license and gutting the regime of financial resources. Soon enough, a tougher sanctions regime would isolate Venezuela. Rubio and Secretary of War Pete Hegseth grabbed the spotlight. Grenell found himself sidelined, but kept insisting his approach was the right one.
“I continue to talk to Maduro’s team,” Grenell told CBS after returning from CPAC, which featured the likes of presidents Santiago Peña and Javier Milei, and right-wing commentator Javier Negre, a Spanish media figure whose visibility in “Twitterzuela” has grown for praising Delcy Rodríguez and criticizing María Corina Machado’s camp.
Donald Trump shut Grenell down via telephone two weeks later, according to The New York Times, in the middle of an Oval Office meeting with senior military leaders. Grenell reportedly received orders to cease all communications with Maduro’s camp.
The aftermath of January 3 would further push him out. Rubio took an active role in handing instructions and often dealing directly with Delcy Rodríguez. In March, Grenell was relieved of his duties as president and executive director of the Kennedy Center. He formally retains the “Special Missions” post, but has stayed off the radar while other names (Claver-Carone, Alejandro Betancourt, Chris Wright and Jarrod Agen, to name a few) gained prominence over the Caracas dossier.
The unlucky colleagues
A string of successive scandals has also affected other Trump administration officials, who had to resign from their posts last week. Evidence available from open sources indicate two of them are close to Grenell.
The latest example is Katie Zacharia, the shortest-serving Press Secretary in the history of the White House. Following a clumsy first (and last) press briefing, Zacharia faced scrutiny over the false claim that she was an attorney. Some quick fact-checking from US media and observers found that Zacharia was neither licensed to work as counsel in the US nor that she worked as a lawyer in China, as she alleged at some point. Her LinkedIn page says she served as “general counsel” for Fix California, a non-profit that Grenell launched in 2021. The organization is focused on voter registration and advancing conservative causes in the Golden State, the liberal stronghold run by Democratic Governor Gavin Newsom—a constant target of Grenell’s attacks on social media.
Last year, Zacharia appeared twice in conservative media hailing Grenell’s work in Venezuela. On Fox News Night in February 2025, she recounted how Grenell supposedly forced Maduro to give in:
People didn’t know these hostages [American political prisoners in Venezuela] were in Venezuela. He asked Maduro: “I want these six hostages,” and he said, “Oh, I don’t have them.” And Ambassador Grenell said: “I need them, I’m gonna go back to the airplane and you’re gonna get them for me.” And the regime brought them to him…
The other disgraced ally of Grenell is Kimberly Guilfoyle, the ex-fiancée of Donald Trump Jr. (and Gavin Newsom’s ex-wife), who served as the US ambassador in Athens until last week. Guilfoye’s dismissal was actually the only news Katie Zacharia shared during her only presser.
Guilfoyle, whose fondness for parties and luxury was no secret, faced rising scrutiny in September. The Wall Street Journal reported that a Greek-American lobbyist had become a constant presence alongside her in official meetings across the Balkans, promoting energy deals with a Greek construction company. Then, the same journalists found that Guilfoyle asked a Trump donor to pay her $100,000 credit card bill just before her confirmation hearing. Despite some initial denial, the episode went on to exhaust Rubio and Trump, who forced her to resign last week.
The president also fired Paolo Zampolli last week, who served as special envoy for global partnerships. A longtime modeling agent, Zampolli is credited with introducing Donald Trump to Melania in 1998.
Public records show that Grenell has also had interests in Southeastern Europe, where association with pro-Russian autocrats and involvement in controversial deals continue to dog MAGA and Trump’s own inner circle. Having served as special envoy for Kosovo-Serbia negotiations during Trump’s first term, Grenell maintains a close relationship with Aleksandar Vučić, Serbia’s increasingly authoritarian leader, who recently resigned the presidency to run for prime minister in a bid to further entrench his power. After leaving that post, Grenell advocated for a major luxury complex in central Belgrade backed by Jared Kushner’s investment firm.
In Romania, Grenell drew scrutiny for publicly opposing proceedings against internet personalities Andrew and Tristan Tate, who face severe criminal charges including human trafficking and rape across multiple jurisdictions.
Grenell, Machado and the Rodríguez siblings
A Venezuelan opposition insider suggests Grenell’s sidelining helped put an end to media noise about the Trump administration pursuing a diplomatic and commercial understanding with Maduro in 2025.
Grenell first came into contact with Maduro associates in 2021, when Florida politician David Rivera and Raúl Gorrín coordinated a backchannel meeting in Mexico City between Jorge Rodríguez, Grenell and Erik Prince. Delcy’s brother offered to swap six American prisoners for Alex Saab, then in US custody for the first time. Rivera, who couldn’t make it to the encounter, faces a decade in prison for secretly lobbying on behalf of Maduro during Trump’s first term—an operation orchestrated by Delcy Rodríguez, who finally achieved an understanding with Washington this year.
Grenell was perceived as a nuisance for regime-change ambitions among many opposition figures and observers. María Corina Machado had contact with Grenell in early 2025, but the relationship soured before long. Two senior members of Machado’s team were approached for a comment on Grenell’s role and relationship with their camp. Neither has replied so far.
Grenell reportedly sought to meet the opposition leader in person while she was hiding in Venezuela. The New York Times reported that she refused to provide a list of political prisoners who Grenell could prioritize during negotiations with chavista representatives. Grenell later voiced his displeasure when Machado won the Nobel Prize instead of his boss, claiming in a tweet that the award had “died years ago.”
Now, both Machado and Grenell appear to lack Trump’s confidence. But Machado is expected to find her way back to Venezuela, one way or another, while Grenell could face disgrace, deprived from the opportunity of providing access to the investment rush “down in V.”