Embattled Secretary of Defense Pete Hegseth assumed his role with a clear mission in mind: “DEI is going to be ripped out root and branch,” he said on Fox News four days after taking office. His deputy secretary, billionaire investor Steve Feinberg, has a different perspective, having spent nearly $40 million on scholarship programs for Black students in recent years—making diversity, equity and inclusion initiatives the largest recipients of grants from his foundation.

Feinberg’s commitment to the cause began in 2020, the year George Floyd’s murder sparked a national outcry. The biggest beneficiary appears to be Tuskegee University, which received a $5 million grant from Feinberg’s foundation that year, one of the largest gifts ever for the historically Black school. A press release issued at the time said the money would go toward scholarships for needy students. The famously private Feinberg did not provide any quotes for the announcement, but his foundation issued a statement with no name attached to it. “We’re very pleased to honor our founder’s philanthropic vision,” it said, “with a grant that has real potential to advance racial equity in postsecondary education.” Money continued to pour in from Feinberg’s foundation over the ensuing years, eventually reaching about $20 million.

The investor also bankrolled a similar effort through the Thurgood Marshall College Fund, to which he gave another $5 million in 2020. That organization then provided $8,500 a year to about 60 students, who had to be Black or of African descent to qualify. Another organization that received big money from Feinberg: the Congressional Black Caucus Foundation, a nonprofit connected to the all-Democrat group on Capitol Hill. The Black caucus foundation helps with the Stephen Feinberg Multi-Year Scholarship Program, which provides African-American and Black undergrads with $10,000 a year for up to four years. Feinberg has now contributed at least $13 million to the group.

Asked about all of this—and how it jibed with Secretary Hegseth’s comments—a spokesperson for Feinberg issued a carefully worded statement that tried to make it seem like the defense department leaders are on the same page about DEI matters, without actually saying that explicitly. “Deputy Secretary Feinberg is fully aligned with Secretary Hegseth’s priorities,” the spokesperson, Eric Pahon, said in a statement. “His many charitable donations have gone to organizations that prioritize merit and performance to build a stronger America, and today he is working with Secretary Hegseth to advance those same values for a stronger military.”

Feinberg grew up in a modest home in Spring Valley, New York, then worked on Wall Street, where he eventually opened his own firm, Cerberus Capital Management. It invested in Chrysler, Fila and debt tied to Donald Trump’s tower in Chicago, ultimately growing to manage about $70 billion in assets. Overseeing so much money for others provided Feinberg with plenty of his own—an estimated $5 billion. At the end of 2015, he dumped $130 million into a private foundation.

He initially gave to the sorts of causes that lots of billionaires support—a hospital near his home and the university he attended, Princeton, where Feinberg did R.O.T.C., played tennis and left an impression on classmates. “When he walked across campus, you know, he was in his own world,” says someone who knew him back then. “He was kind of a force unto himself.”

In 2017, Feinberg sprinkled in some contributions that hinted at his interest in politics and national defense. He gave $400,000 to Turning Point USA, the conservative student group led by Trumpworld insider Charlie Kirk. Feinberg handed over another $150,000 to the National Cryptologic Museum, which houses all sorts of code-making-and-breaking artifacts in a building next to the National Security Agency’s headquarters. Another $176,000 went to the Institute for State Effectiveness, a nonprofit focused on nation-building cofounded by Afghanistan’s former president, Ashraf Ghani.

The following year, in 2018, Feinberg became chair of Trump’s Intelligence Advisory Board. He devoted not just time to national-security issues but also money—his foundation dispersed $5 million to In-Q-Tel, a venture-capital nonprofit created by the Central Intelligence Agency that has that has backed companies including Palantir, Databricks and Anduril. Smaller donations went to Princeton, New York Presbyterian hospital, Turning Point USA and the U.S. Chamber of Commerce Foundation.

Feinberg continued focusing on defense in 2019, this time contributing $5 million to a subsidiary of the multibillion-dollar nonprofit Mitre, which operates federally funded research and development facilities. The subsidiary focused on enhancing private-sector collaboration in many of the same areas in which Feinberg has invested—telecommunications, cybersecurity, unmanned aviation. A tax return for his foundation listed a $5 million “returned grant” as income in 2019—it’s unclear if In-Q-Tel, the Mitre subsidiary or someone other organization sent its money back.

The world changed in 2020, and Feinberg’s philanthropic strategy adapted with it. As Covid-19 swept the globe, Feinberg quadrupled his donations to New York Presbyterian hospital from $250,000 to $1 million. Two months after the pandemic landed, on May 25, 2020, a white police officer kneeled on the neck of George Floyd. Like many corporate leaders, Feinberg decided to do something.

For help, he turned to Greg Nixon, a Black executive at Cerberus with a personal story that underscored the promise of historically Black universities. After graduating from Tuskegee, Nixon joined the U.S. Air Force, became an intellectual property attorney inside the government and moved into the private sector, where he worked for McKinsey, Booz Allen Hamilton and DynCorp. He advised Tracker Capital, the family office that Feinberg used to make some of his defense-related deals and ultimately became the head of strategic investments at Cerberus. With Nixon at his side, Feinberg funneled tens of millions of dollars to Tuskegee University, the Thurgood Marshall College Fund and the Congressional Black Caucus Foundation. Feinberg’s Wall Street firm, meanwhile, launched internal committees to support women and promote inclusion. “Cerberus is fully committed to DEI,” Nixon explained on a panel hosted by one of the firm’s legal partners.

A few years later, as Feinberg awaited confirmation to become deputy secretary of defense, President Trump issued an order making it clear that his priorities were the opposite. On his first day in office, the president demanded the removal of all diversity, equity and inclusion considerations in federal employment. Hegseth vowed to root out DEI efforts from the military. And, shortly after the new administration arrived in town, the Air Force reportedly briefly removed training material with videos of Tuskegee airmen, Black World War II heroes.

Meanwhile, Feinberg lined up a strategy to divest from his multibillion-dollar business empire and move into public office. Rather than sell his assets, he planned to give them to family and charity. On March 17, the day Feinberg became deputy secretary of defense, Tuskegee University announced that his foundation donated $6.2 million, more than ever before.