President Donald Trump delivered a cryptic warning to American oil executives weeks before U.S. forces moved to capture Venezuelan leader Nicolás Maduro: “Get ready.” According to reporting by the Wall Street Journal, the comment hinted at sweeping changes ahead for Venezuela, underscoring how central oil was to Trump’s high-stakes decision to intervene in the country.
While Trump did not disclose details of the military operation or seek industry input on the plan, the Journal reported that his message highlighted the administration’s intent to draw U.S. energy companies into revitalizing Venezuela’s shattered oil sector. Trump publicly framed the strategy as an economic reset, saying major American oil companies would invest billions to repair infrastructure and extract vast reserves that he said would benefit both Venezuela and U.S. interests.
White House officials said Energy Secretary Chris Wright and Secretary of State Marco Rubio are leading outreach efforts to oil companies, with early correspondence already underway. The administration sees expanded oil production as a way to stabilize Venezuela’s economy, reduce migration pressures and keep global energy prices in check. Venezuela claims to hold roughly 300 billion barrels of oil reserves, though its current output of about 900,000 barrels a day is a fraction of global supply.
Investors responded positively to the prospect of a reopened Venezuelan oil frontier. Chevron shares rose about 5% following the operation, while Exxon Mobil and ConocoPhillips also posted gains. Still, enthusiasm inside the industry remains cautious. The Wall Street Journal reported that Chevron, the only major U.S. oil company still operating in Venezuela, is wary of committing significant new capital until political stability improves and commercial terms are clarified.
Chevron executives have emphasized employee safety, legal certainty and the ability to repatriate profits as prerequisites for expansion. The company has not advocated regime change and has no immediate plans to ramp up production, according to people familiar with the matter. Other oil majors, including Exxon and ConocoPhillips, have signaled little interest in returning to a country that nationalized their assets in the mid-2000s.
Analysts warn that the reluctance of oil companies could undermine the administration’s broader strategy. Dan Pickering of Pickering Energy Partners told the Wall Street Journal that companies would need robust protections against political risk, including future policy shifts in Washington, before committing billions to Venezuela.
Even as oil executives weighed their options, unusual trading activity on prediction markets raised fresh controversy. Less than five hours before explosions rocked Caracas, an anonymous trader placed a series of bets on Polymarket predicting Maduro’s imminent removal. The wagers, placed through a newly created account, ultimately generated nearly $410,000 in profit on about $34,000 in bets.
The timing and concentration of the bets fueled suspicions of insider knowledge. Polymarket contracts that paid out if Maduro lost power were trading at prices implying only an 8% chance of such an outcome shortly before Trump authorized the military operation. The Wall Street Journal reported that the administration kept the plan tightly held among a small circle of advisers to preserve secrecy, involving coordination across multiple military branches.
Unlike traditional financial markets, prediction platforms such as Polymarket face limited regulatory oversight. Legal experts told the Journal that while U.S. officials misusing nonpublic information could face prosecution, enforcement becomes murkier if trades are placed overseas or by foreign nationals. Polymarket officially bars U.S. users, but traders can bypass restrictions using virtual private networks.
The incident has renewed calls for stricter rules. Representative Ritchie Torres said he plans to introduce legislation to bar federal officials from betting on prediction markets tied to nonpublic information. Polymarket’s leadership has argued that community scrutiny and internal audits help deter abuse, though past controversies have continued to attract attention.
As the dust settles in Caracas, Trump’s Venezuela strategy faces twin tests: whether U.S. oil companies will risk billions to revive a battered energy sector, and whether regulators can keep pace with a new frontier of markets where geopolitical secrets can quickly become lucrative wagers.
