(This is a facebook post, . I normally don't post those as fact or credible but I did find a supporting article.)
Okay - y’all basically bullied me into researching the CITGO deal - so here’s what I found.
You know how some people flip houses? Paul Singer flips countries.
I’m not being hyperbolic. This man’s whole thing - his entire career - is finding nations in financial ruin, buying their debt for basically nothing, and then hounding them through every court on earth until they pay him back at full price plus interest. He did it to Peru. He did it to the Republic of Congo. He’s currently doing it to Venezuela. But Argentina is the one that made him famous.
Like in 2001 when Argentina’s economy imploded. People were rioting. The government defaulted on $100 billion in debt. Most creditors looked at this disaster and thought okay, we’ll take thirty cents on the dollar and cut our losses. Not Paul Singer. He looked at Argentina’s smoldering economy and saw a decade-long payday. His fund bought up bonds for $117 million and then just… waited. And sued. And waited some more. And sued in different countries.
At one point - and I cannot stress enough that this actually happened - Singer’s lawyers convinced a court in Ghana to seize an Argentine naval ship that had docked there. The ship. With the crew still on it. Argentina’s president went on television and said this man can have our boat but he will never have our dignity. The crew was stuck there for weeks while everyone screamed at each other.
Fifteen years later, Argentina elected a new president who wanted to rejoin international markets. Singer collected $2.4 billion. That’s twenty times his original investment. For buying paper and being annoying about it for a decade and a half.
Wall Street calls this “distressed debt investing.” Argentina called him a vulture. Singer doesn’t seem to mind the nickname.
Anyway. Venezuela.
Venezuela has this company called CITGO. You’ve seen their gas stations. What you might not know is that CITGO is actually owned by Venezuela’s state oil company and it’s the crown jewel of their foreign assets. Three huge refineries. Forty-three oil terminals. Over 4,000 gas stations. The whole thing was valued somewhere between $11 billion and $18 billion depending on who you ask.
Problem is, Venezuela owes a lot of people a lot of money. Mining companies that got nationalized. Oil companies with unpaid contracts. Bondholders who never got paid. The debts piled up past $20 billion. A few years ago, a Canadian mining company went to a court in Delaware and said hey,
Venezuela won’t pay us, can we just take their stuff? And the court said sure.
CITGO goes up for auction.
Singer swoops in. His hedge fund bids $7.28 billion in September 2024. Already way below the valuation. But by the time the sale actually closes in November 2025, the price has dropped to $5.9 billion. Why so cheap? Well, CITGO’s refineries were specifically built to process Venezuelan crude oil, but U.S. sanctions cut off that supply. The company had to buy more expensive oil from other countries. Also the Venezuelan government was fighting the sale tooth and nail, calling it “the theft of the century” and filing appeals everywhere.
Singer gets a $13 billion company for $5.9 billion because it’s damaged.
And then.
Two months later.
The United States military captures the president of Venezuela.
Let that sit for a second.
Over 150 aircraft. Delta Force. At one in the morning, American soldiers land at Venezuela’s biggest military base, grab Nicolás Maduro and his wife from their home, and fly them out on a helicopter to a Navy ship. They’re now in New York facing drug charges.
Trump holds a press conference the next day. He says America is going to “run” Venezuela for a while. He says American oil companies are going to go in and “start making money.” He says he tipped off oil executives before the strike. He did not say which ones.
The Venezuelan government that was fighting Singer’s purchase of CITGO? Currently in a New York jail cell.
The appeals they filed? Kind of hard to pursue legal action when your entire executive branch got kidnapped.
The sanctions that were crushing CITGO’s profitability? Suddenly very negotiable when Washington is calling the shots in Caracas.
Now. Let me tell you about Paul Singer’s political donations.
In 2024, he gave $5 million to Trump’s Super PAC. He gave tens of millions to Republican congressional campaigns over the years. He gave $1 million to Trump’s first inaugural fund and some undisclosed amount to the second one. He’s met with Trump multiple times since 2016.
He also funds think tanks. The Manhattan Institute - where he was board chairman for seventeen years - has been publishing papers for months about how Maduro needs to go. “The question that remains is how to remove Maduro from power,” one of their guys wrote last summer. The Foundation for Defense of Democracies, another Singer-funded operation, put out a report in November 2025 explicitly calling for military strikes in Venezuela. A month before the military strikes in Venezuela.
Oh and he’s currently spending a million dollars to defeat Thomas Massie, a Republican congressman from Kentucky, because Massie voted against Israel aid and keeps demanding the Epstein files get released. Singer and a couple other billionaires dumped $2 million into a Super PAC specifically to end this man’s career. Trump endorsed Massie’s opponent.
After the Venezuela thing, Massie posted that Singer “stands to make billions of dollars on his distressed Citgo investment, now that this administration has taken over Venezuela.”
The math here is not subtle. Singer paid $5.9 billion. The company was valued at $11-13 billion in its damaged state. If Venezuelan crude starts flowing to those refineries again - which seems pretty likely when the U.S. is “running” Venezuela - CITGO could easily be worth its original valuation or more. That’s somewhere between $5 billion and $7 billion in profit. Singer’s net worth is estimated around $6-7 billion. This one deal could double his entire fortune.
Did he know the invasion was coming? Did he and Trump chat about it during one of their meetings? I have no idea. What I know is that a man who has spent forty years buying distressed sovereign assets and waiting for political winds to change just happened to buy Venezuela’s most valuable company two months before the U.S. military removed the government that was blocking his purchase.
The same playbook as Argentina. Buy the debt. Wait for regime change. Collect.
Some people see a country in crisis and feel sympathy. Paul Singer sees a buying opportunity. And somehow, the policies of the United States government keep aligning perfectly with his portfolio.
