The millionaire anti-war activist who organized a high-profile "humanitarian aid" convoy to Cuba in March, a trip that included Rep. Ilhan Omar's daughter and leftist streamer Hasan Piker, has a long trail of direct engagement with Hamas officials and the Iranian regime, the New York Post reported in an exclusive investigation.

Medea Benjamin, 73, serves as president of the Arc of Justice Foundation, a charity sitting on $51 million. She co-founded the activist group CodePink. And between 2009 and 2012, she made at least seven trips to Gaza, where publicly posted photos show her meeting with Hamas officials, including the group's then-leader Ismail Haniyeh. The United States designated Hamas a terrorist organization in 1997.

That history matters now because Benjamin organized the so-called "Nuestra America Convoy," which delivered 20 tons of aid to Cuba in March. On the trip were Isra Hirsi, Omar's 23-year-old daughter, and Piker, the popular left-wing internet personality. Both later praised the Communist island. Some delegates reportedly stayed at the five-star Gran Hotel Bristol Meliá Collection, where rooms run between $130 and $520 a night.

A letter hand-delivered to Obama, from Hamas

The connections between Benjamin and Hamas go well beyond photo opportunities. Working under the CodePink banner, Benjamin and fellow activist Tighe Barry, 69, met Hamas leaders including foreign affairs minister Ahmed Yusef. In 2009, Yusef, described as "Hamas's gate to the West", handed Benjamin and Barry a letter addressed to President Obama.

The pair promptly delivered the letter to the U.S. Embassy in Cairo on June 4, 2009. At the time, the appointed U.S. administration official was refusing to meet with Hamas. Yusef was then a senior advisor to Gaza Prime Minister Ismail Haniyeh, who was later assassinated in Tehran in 2024.

A report from the Network Contagion Research Institute, a New Jersey-based think tank that studies extremism, laid out the significance plainly:

"CodePink is open about being a conduit between Hamas and Obama, even met with Obama administration official Buffy Wicks at the White House after the letter was delivered. That's a remarkable acknowledgment of the intermediary role."

Federal law makes it a crime to knowingly provide material support or resources to a designated foreign terrorist organization. Legal experts cited by the Post noted the potential implications of acting as an intermediary for Hamas.

Benjamin told the Post she has "consistently been against war" and has "always encouraged my government, no matter who is in power, to choose the path of diplomacy." She said she is "no longer on the board" of Arc of Justice and is "not connected to any foreign entity," describing herself as "simply an American citizen who believes in citizen diplomacy and peace."

Iran trips and an IRGC-linked conference

The Hamas meetings were not an isolated chapter. Benjamin has also made multiple trips to Iran, the NCRI report found. In 2014, she attended a conference in Tehran where she presented a strategy on Gaza to advance Boycott, Divestment, and Sanctions (BDS) efforts against Israel.

Five years later, she led a 28-person CodePink delegation to Tehran, Isfahan, and Shiraz. The group met with then-Iranian foreign minister Mohammad Javad Zarif at the foreign ministry offices in Tehran.

That same year, Benjamin attended a conference in Iran that the U.S. Treasury Department designated as a platform used by the Iranian Revolutionary Guards Corps to "recruit and collect intelligence" from foreign attendees. The IRGC is itself a designated foreign terrorist organization.

The pattern is hard to miss. Meetings with Hamas leadership. A hand-delivered letter to the Obama administration from a terror group. Conferences hosted by IRGC fronts. And now, organizing politically charged convoys to Communist Cuba, with the daughter of a sitting U.S. congresswoman along for the ride. The White House has already signaled its interest in scrutinizing Rep. Omar on other fronts, and this latest report adds another dimension to the broader picture.

The money trail and Florida's charity laws

Benjamin's Arc of Justice Foundation, previously called the Benjamin Fund until 2018, holds $51 million and is run in conjunction with her daughter, Maya Mandela Danaher, who is listed as treasurer and lives in a $2 million Manhattan apartment. The charity has moved from California to Washington, D.C., then to New York, and now operates out of a modest bungalow in North Miami owned by Barry.

Arc of Justice did not respond to the Post's request for comment. Notably, the charity did not disclose that it was helping to finance politically motivated trips to Cuba, a potential problem under Florida law.

The Florida Department of Agriculture and Consumer Services lists Cuba as "a foreign country of concern" and requires registration before doing business with the island, though it remains unclear whether providing aid qualifies as "business" under the statute. A senior NCRI researcher told the Post that Benjamin "signs the checks, she cashes the checks and then runs the Cuba operations the checks pay for, all through an unregistered charity. It appears to be operating in violation of Florida law."

The Cuba convoys have been organized through the Cuban Institute of Friendship with Peoples, or ICAP, which is run by Fernando Gonzalez Llort. Gonzalez Llort was convicted in U.S. federal court in 2001 of spying and collecting information on Cuban exile groups. He served nearly 14 years in a U.S. prison.

So the charity coordinating the aid convoys works through an organization led by a convicted Cuban spy. That is the institutional pipeline through which Omar's daughter and Piker traveled to Havana.

CodePink's web and the Cuba trip's famous passengers

CodePink was started by Jodie Evans, the wife of China-based software entrepreneur and activist Neville Singham. Benjamin co-founded the group and is still listed as treasurer in the latest available federal filings. Barry served as CodePink's spokesman for over a decade. Both Benjamin and Evans were on the March Cuba trip alongside Hirsi and Piker.

After the trip, Hirsi posted on Instagram about the experience. The Barnard graduate wrote that living through blackouts on the island "truly changed me," adding:

"As Americans, bringing aid to Cuba is the least we could do, as the US has long bullied Cuba with its sanctions, and now this oil blockade is killing people."

That framing, the United States as the bully, Cuba as the victim, tracks with the broader ideological project Benjamin and CodePink have advanced for years. Omar herself has drawn repeated scrutiny for rhetoric that critics say minimizes the conduct of hostile foreign regimes while placing blame squarely on the United States.

Florida Lieutenant Governor Jay Collins offered a blunt assessment of the dynamic:

"One of the great ironies of the modern left is that groups like CodePink claim to stand for human rights while repeatedly carrying water and driving anti-American rhetoric for regimes that imprison women, fund terrorism, crush dissent, and chant 'death to America.' That's not moral clarity. That's ideological blindness disguised as progressivism."

A pattern that keeps repeating

The broader context is damning. Benjamin's network connects Hamas, Iran, Cuba, and a roster of high-profile progressive figures, all channeled through a foundation that appears to have skirted state charity registration requirements while sitting on tens of millions of dollars. The pattern of progressive figures associating with Hamas-linked activists has drawn fierce backlash before, and this case adds another well-documented example.

Several questions remain unanswered. Did Hirsi or Piker know about Benjamin's history with Hamas and the IRGC-linked conference before joining the convoy? Did any federal agency review the Cuba trips for compliance with sanctions law? And why has a $51 million charity been allowed to operate out of a North Miami bungalow without apparent disclosure of its politically charged activities?

The contrast between how the two parties handle these associations remains stark. When figures on the right are linked to extremism, the consequences tend to be swift. On the left, the same associations get repackaged as "citizen diplomacy" and "peace", and the convoys keep rolling.

You can call it activism. You can call it diplomacy. But when the meetings are with Hamas, the conferences are IRGC recruitment platforms, and the charity paperwork doesn't add up, ordinary Americans have a simpler word for it: accountability, and it's long overdue.