CEOs on High Alert as Trump Disrupts Businesses with New Executive Orders

For American CEOs, navigating the complexities of a Donald Trump presidency is proving to be more challenging in his second term. This administration uniquely blends traditional conservative deregulation with a populist approach that intervenes in big business.

Recently, Trump has unleashed a series of demands aimed at corporate leaders, all in an effort to bolster his political standing as midterm elections loom. He signed an executive order urging defense contractors to halt stock buybacks, specifically targeting Raytheon, a key player in the aerospace and defense sector known for supplying the Patriot missile system and Pratt & Whitney jet engines to the Defense Department.

Following a surprising military action that led to the ousting of Venezuelan President Nicolás Maduro, Trump announced that major oil companies would invest billions into Venezuela’s oil sector—a move that seems unlikely to have originated from the companies themselves.

This week, Trump also proposed banning institutional investors like Blackstone Inc. from purchasing single-family homes, aiming to combat rising living costs. He praised Intel Corp. CEO Lip-Bu Tan after their White House meeting, highlighting a “great deal” for the federal government to acquire up to 10% of the chipmaker.

These actions reflect an unprecedented willingness to intervene in the private sector, a stark departure from the norms of previous Republican administrations. This week, Trump also made headlines on the global stage, arresting Maduro and vaguely threatening other nations in the Western Hemisphere, while even revisiting the controversial idea of acquiring Greenland.

One year into Trump’s second term, his deregulatory agenda and government cost-cutting measures are more aggressive than during his first term. Some businesses are pushing back; over 1,000 firms have joined lawsuits challenging Trump’s tariffs across various sectors. However, corporate executives note that the current administration is more open to dialogue, with regular communication compared to the previous Biden administration, which maintained a tighter circle around the former president.

Despite putting CEOs on alert, Trump remains eager for the approval of big business and Wall Street. This dynamic was evident during a recent summit at the White House with leaders from major oil companies, including Chevron Corp. and Exxon Mobil Corp., where he pledged $100 billion of their capital toward rebuilding Venezuela’s oil sector. Industry insiders, however, expressed skepticism about such investments given the current political climate and oil prices.

During the meeting, Exxon CEO Darren Woods highlighted the risks, noting that the company had previously faced asset seizures in Venezuela. “Today, it’s uninvestable,” he stated, emphasizing the challenges of re-entering the market.

After the summit, Trump took to Truth Social, calling for a one-year cap on credit card interest rates at 10%, effective January 20, without providing further details.

For many in the C-suite who previously welcomed Trump’s policies on taxation and regulation, managing these new complexities is becoming increasingly difficult. At the start of Trump’s first term, executives at United Technologies Corp. felt optimistic about potential tax reforms that could unlock $6 billion in overseas cash, paving the way for significant stock buybacks.

However, navigating Trump’s whims in 2026 is proving to be a different story. Recently, Trump’s impulsive demand to add $500 billion to the Pentagon budget sent defense stocks soaring, but he also criticized defense contractors, including Raytheon, for stock buybacks and executive pay.

RTX has yet to comment on Trump’s remarks. The Aerospace Industries Association, representing defense contractors, expressed its commitment to working with the administration on national security concerns.

Corporate consultants report that their clients are increasingly focused on avoiding Trump’s ire while strategizing responses to potential future interventions. The Republican Party has shifted from a pro-business stance to one that increasingly aligns with Trump’s populist tendencies, embracing government intervention that would have been unthinkable in the past.

This week, some Democrats supported limiting buybacks, while Republican lawmakers surprisingly refrained from objection. House Armed Services Committee Chairman Mike Rogers noted that defense companies seem more concerned with quarterly reports than national defense, echoing Trump’s frustrations.

Copyright 2026 Bloomberg.

For American CEOs, navigating the complexities of a Donald Trump presidency is proving to be more challenging in his second term. This administration uniquely blends traditional conservative deregulation with a populist approach that intervenes in big business.

Recently, Trump has unleashed a series of demands aimed at corporate leaders, all in an effort to bolster his political standing as midterm elections loom. He signed an executive order urging defense contractors to halt stock buybacks, specifically targeting Raytheon, a key player in the aerospace and defense sector known for supplying the Patriot missile system and Pratt & Whitney jet engines to the Defense Department.

Following a surprising military action that led to the ousting of Venezuelan President Nicolás Maduro, Trump announced that major oil companies would invest billions into Venezuela’s oil sector—a move that seems unlikely to have originated from the companies themselves.

This week, Trump also proposed banning institutional investors like Blackstone Inc. from purchasing single-family homes, aiming to combat rising living costs. He praised Intel Corp. CEO Lip-Bu Tan after their White House meeting, highlighting a “great deal” for the federal government to acquire up to 10% of the chipmaker.

These actions reflect an unprecedented willingness to intervene in the private sector, a stark departure from the norms of previous Republican administrations. This week, Trump also made headlines on the global stage, arresting Maduro and vaguely threatening other nations in the Western Hemisphere, while even revisiting the controversial idea of acquiring Greenland.

One year into Trump’s second term, his deregulatory agenda and government cost-cutting measures are more aggressive than during his first term. Some businesses are pushing back; over 1,000 firms have joined lawsuits challenging Trump’s tariffs across various sectors. However, corporate executives note that the current administration is more open to dialogue, with regular communication compared to the previous Biden administration, which maintained a tighter circle around the former president.

Despite putting CEOs on alert, Trump remains eager for the approval of big business and Wall Street. This dynamic was evident during a recent summit at the White House with leaders from major oil companies, including Chevron Corp. and Exxon Mobil Corp., where he pledged $100 billion of their capital toward rebuilding Venezuela’s oil sector. Industry insiders, however, expressed skepticism about such investments given the current political climate and oil prices.

During the meeting, Exxon CEO Darren Woods highlighted the risks, noting that the company had previously faced asset seizures in Venezuela. “Today, it’s uninvestable,” he stated, emphasizing the challenges of re-entering the market.

After the summit, Trump took to Truth Social, calling for a one-year cap on credit card interest rates at 10%, effective January 20, without providing further details.

For many in the C-suite who previously welcomed Trump’s policies on taxation and regulation, managing these new complexities is becoming increasingly difficult. At the start of Trump’s first term, executives at United Technologies Corp. felt optimistic about potential tax reforms that could unlock $6 billion in overseas cash, paving the way for significant stock buybacks.

However, navigating Trump’s whims in 2026 is proving to be a different story. Recently, Trump’s impulsive demand to add $500 billion to the Pentagon budget sent defense stocks soaring, but he also criticized defense contractors, including Raytheon, for stock buybacks and executive pay.

RTX has yet to comment on Trump’s remarks. The Aerospace Industries Association, representing defense contractors, expressed its commitment to working with the administration on national security concerns.

Corporate consultants report that their clients are increasingly focused on avoiding Trump’s ire while strategizing responses to potential future interventions. The Republican Party has shifted from a pro-business stance to one that increasingly aligns with Trump’s populist tendencies, embracing government intervention that would have been unthinkable in the past.

This week, some Democrats supported limiting buybacks, while Republican lawmakers surprisingly refrained from objection. House Armed Services Committee Chairman Mike Rogers noted that defense companies seem more concerned with quarterly reports than national defense, echoing Trump’s frustrations.

Copyright 2026 Bloomberg.