Oracle founder Larry Ellison quietly funneled around $45 million into a tax-exempt organization supporting President Donald Trump’s 2024 campaign — one of the cycle’s largest single checks — and a detailed new investigation suggests the billionaire’s generosity has generated extraordinary returns for both his software company and his son’s rapidly expanding media holdings.
A Friendship Worth Billions
The donation passed through a vehicle specifically designed to avoid public disclosure requirements, keeping it concealed until now. At 81, Ellison is just a year older than the president, and the two men have built a relationship that has delivered concrete rewards on multiple fronts, The Wall Street Journal reports. The morning after Trump’s second swearing-in, Oracle secured the anchor role in a sweeping $500 billion government-backed initiative to construct artificial intelligence data centers across the United States.
The optics of that arrangement became apparent even before the announcement was made. Ellison arrived at the unveiling event without identification, and security personnel initially stopped him at the door. President Trump resolved the situation personally, telling guards “Everyone knows” who Larry is. White House spokesperson Kush Desai later brushed aside questions about favoritism, saying Trump is “committed to working with every American business and business leader.”
Beyond the infrastructure contract, Oracle also entered a consortium purchasing TikTok’s U.S. operations in a government-facilitated deal. Additionally, federal disclosures show brokerage accounts linked to President Trump traded Oracle shares this year in transactions each topping $1 million, though the Trump Organization stated the president does not direct such investment choices.
David Ellison’s Media Ascent
Larry Ellison’s proximity to power has apparently benefited his son David, 43, who runs Skydance Media. David completed an $8 billion purchase of Paramount and its properties, including MTV, Comedy Central, and CBS News. The Trump administration approved the merger, and the Justice Department later authorized an even larger deal: Paramount Skydance’s $81 billion purchase of Warner Bros. Discovery, which would place CNN under Ellison family control. The president has privately praised David’s ascent, and Larry reportedly told Trump that owning Paramount could grant the family substantial influence over CNN’s coverage.
Ellison co-founded what would eventually become Oracle Corporation back in 1977 under the name Software Development Laboratories, seeding it with just $2,000. Today the software giant’s market capitalization surpasses $800 billion, with Ellison retaining approximately 40% ownership. He stepped down as chief executive in 2014 but never fully retreated from the spotlight, and his ambitions have only expanded since Trump returned to the White House.
Turbulence Inside CBS News
The Ellison family’s imprint on CBS News has been unmistakable and deeply contentious. David Ellison installed Bari Weiss, co-founder of the conservative-leaning Free Press, as the network’s top news executive. Under Weiss, CBS pushed out veteran 60 Minutes executive producer Tanya Simon along with longtime on-air correspondents Sharyn Alfonsi and Cecilia Vega. The storied program was then handed to Nick Bilton, a former technology columnist with no prior broadcast experience, who said veteran correspondent Scott Pelley’s “antipathy to” the future of the show was the reason for his dismissal.
Scott Pelley, a 37-year fixture at the network, erupted at a June staff meeting, accusing Weiss of effectively destroying one of American journalism’s most recognized brands. CBS fired him the following day. Pelley said new leadership had pushed him to “inject falsehoods and bias” into sensitive reporting and told the New York Times that Weiss sought to portray immigration protesters in Minnesota as more menacing than reality warranted. He described the upheaval as designed to “curry a moment of favor with the Trump administration.”
Critics Question Democracy’s Cost
For Ellison, the financial calculus behind his political spending has so far tilted decisively in his favor. Oracle’s valuation has soared alongside its AI infrastructure contracts, and the company has secured a coveted role in the broader tech ecosystem reshaping the American economy. Oracle is now listed among the backers of Freedom250, a Trump-aligned organization organizing events to commemorate the nation’s 250th anniversary.
Media watchdogs and press freedom advocates have grown increasingly alarmed by the concentration of editorial power flowing toward a family with such deep financial ties to the sitting administration. Whether regulators, lawmakers, or the public will demand greater scrutiny of those entanglements — or whether the Ellisons’ deal-making will simply continue expanding unchallenged — remains the central question hanging over one of the most unusual billionaire-to-president relationships in modern American political history.
