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“You can’t put a company in jail”: Inside the unconventional tenure of Stanley Woodward, DOJ’s No. 3

2026-11-10T14:22:59-0500 / CBS News

Washington— In an address to some members of the Justice Department’s Antitrust Division in October, Associate Attorney General Stanley Woodward made an unusual pitch.

He wanted to entice the lawyers there to leave their roles and accept temporary stints to help out the National Fraud Enforcement Division, created earlier this year, according to multiple sources with knowledge of the speech.

In a 30-minute talk, he criticized the federal judge overseeing a lawsuit over President Trump’s plans to renovate a public golf course in Washington, and told the group to come to him if they ever have a problem with a judge in the future.

But before he could finish his address, he abruptly left, saying he was getting a call from the president.

The speech offered a glimpse of the unusual role Woodward has carved out as the No. 3 official at the Justice Department.

Since taking office last fall, he has become the de facto leader of the Antitrust Division, put his name on controversial court filings that have bewildered some DOJ employees and voiced a strong philosophical opposition to prosecuting corporations that has shocked many inside the department, multiple sources told CBS News.

Observers say he has developed a pattern of intervening in pending criminal cases involving corporations that are being pursued by the divisions under his remit, often steering them against the recommendations of career prosecutors and even other political appointees.

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Woodward leaves the federal building in Miami in July 2023. Eva Marie Uzcategui T/Anadolu Agency via Getty Images

One example, which has not been previously reported, involved an Illinois mining company that allegedly failed to evacuate its employees during a 2021 fire and failed to report another blaze to regulators as recently as this year, multiple sources told CBS News.

Woodward’s defenders describe him as smart, deeply engaged and willing to take the hits that come with leadership.

A Justice Department spokesperson acknowledged Woodward urged antitrust attorneys to take assignments in the new fraud division, saying some of them have relevant experience.

The spokesperson did not dispute the account of Woodward’s remarks — or the fact they were interrupted by a call from the White House.

“It is well known that Woodward was an advisor to the President prior to coming over to DOJ,” the spokesperson said.

This account of Woodward’s tenure is based on interviews with nearly two dozen people, all of whom asked to remain anonymous to candidly discuss internal deliberations or cases.

The Justice Department did not make Woodward available for an interview.

“The notion that the No. 3 person at the Department of Justice doesn’t believe in the criminal prosecution of corporations is purely an ideological oddity unsupported by law,” said one person familiar with Woodward’s views. “It is a fact that in multiple situations, he has asked prosecutors to justify prosecutions against companies.”

“You can’t put a company in jail”

Woodward has less experience with criminal matters than he does with civil litigation. From 2010 to 2020, he was an associate and senior counsel at the law firm Akin Gump, where he primarily worked on civil matters.

The corporate criminal cases he did work on largely played out behind the scenes, two people familiar with his workload said, making it hard to get a full window into his experience. Most of them involved investigations under the Foreign Corrupt Practices Act, they said,a law that prohibits foreign bribery. He cited one such case on a Senate questionnaire when asked to list the 10 most significant cases of his career, saying he spent six months overseeing a team of lawyers who reviewed documents.

In 2020, he and Stan Brand, a former general counsel for the House of Representatives, started a law firm together. Over the next five years, he represented a number of criminal defendants in Mr. Trump’s orbit, including Walt Nauta and Peter Navarro. He was also counsel to Kelly Meggs, a member of the far-right Oath Keepers who stormed the Capitol on Jan. 6, 2021, and was convicted on multiple felonies, including seditious conspiracy. His sentence was later commuted by Mr. Trump.

While all of the clients he represented during that time who went to trial lost their cases, at least some of the judges in federal court in D.C. seemed to respect him as an attorney.

“The district judges down there loved him,” said one person with knowledge of the cases he handled. “He wasn’t one of those goofy Trump lawyers. He was a by-the-book defense guy. They liked him because he knew what he was doing.”

He briefly worked in the White House as a senior counselor to the president before joining the Justice Department in April 2025 as an aide to then-Attorney General Pam Bondi. He was elevated to associate attorney general that October.

The job of associate attorney general primarily entails overseeing the Justice Department’s civil side: divisions that handle civil rights, antitrust probes, environmental and animal welfare issues, civil enforcement actions, civil tax cases and the offices that defend the government in civil lawsuits. Several of those divisions also have sections that prosecute crimes like price-fixing, air and water pollution violations, and civil rights offenses.

While the majority of his day-to-day job involves civil matters, he has made waves internally when it comes to how he views the smaller subset of corporate criminal cases that fall under his remit, multiple sources said.

In meetings with DOJ attorneys to discuss pending cases, he has been known to often quip that “you can’t put a company in jail” or that there is “no jail big enough for a corporation,” according to multiple sources, including some eyewitnesses.

He also frequently advocates for prosecutors to seek softer resolutions, such as deferred prosecution agreements or civil settlements in lieu of criminal charges, the sources said.

“He openly shows disdain toward every corporate case,” recalled one person who said they have heard Woodward express those sentiments on more than one occasion.

“The impression you get is he doesn’t believe in any of these laws and he does not believe in prosecuting companies at all,” the person added.

His strong views on corporate prosecutions in general — essentially that they shouldn’t happen — have shocked many attorneys at the Justice Department, particularly coming from an office that historically has not been heavily involved in scrutinizing criminal cases, since most of that oversight falls to the office of the deputy attorney general.

They also stand in stark contrast to how most of his predecessors viewed such cases, and even many of his fellow Trump appointees inside the department.

Assistant Attorney General Colin McDonald, for instance, recently ordered prosecutors in the National Fraud Enforcement Division to “zealously prosecute corporate actors that defraud taxpayers and the United States of America.”

On several occasions, Woodward has asked prosecutors to write memos explaining basic legal principles related to prosecuting companies, in what they saw as a sign that he does not have very much experience with corporate criminal work, several sources with knowledge of the requests told CBS News.

In one example, he asked prosecutors to explain the basic “blackletter law” outlining how the Justice Department can even charge a company, one person recalled. The authority to do so was affirmed in a landmark 1909 Supreme Court case which held that companies can be held criminally liable for unlawful acts carried out by personnel acting within the scope of their employment.

Another time, Woodward asked antitrust prosecutors to draft a memo explaining the difference between the “per se rule” and the “rule of reason,” sources with knowledge of the request said. The former is a legal doctrine that DOJ has historically relied upon to criminally prosecute inherently illegal acts like bid-rigging. The latter is a different analytical legal standard that DOJ often applies in most civil antitrust enforcement cases.

A Justice Department spokesperson said Woodward “does not support new and novel theories of prosecution against companies or individuals.”

“But that doesn’t mean companies that break the law should go free writ large — his view is that it’s individuals who break the law and so prosecuting individuals for criminal conduct should always be prioritized,” the spokesperson added.

The clearest recent example of his approach involves M-Class Mining LLC, the Illinois mining company.

A subsidiary of Foresight Energy, M-Class Mining allegedly failed to evacuate its employees during an August 2021 underground fire or alert federal regulators. An indictment in August charged four executives with conspiring to defraud the U.S. and other counts, including obstruction.

Senior political and career officials from the Labor Department and Justice Department had all expressed support for charging the company itself after determining it was plagued by a problematic corporate culture that, in their belief, was not solely caused by a few rogue actors, sources said. Among the aggravating factors was the fact that the company later rehired as a mine safety consultant one of its employees who allegedly obstructed the government.

At first, prosecutors had a green light to pursue a prosecution of the corporation. But Woodward overruled recommendations from both career and Trump-appointed attorneys involved in the investigation.

At one point, Woodward and officials in the deputy attorney general’s office contemplated a deferred prosecution agreement as an alternative, after speaking with the company’s lawyer, Ed O’Callaghan, a former DOJ official who served during Mr. Trump’s first term, sources told CBS News.

But allowing the company to dodge charges through a deferred prosecution agreement ran afoul of the Justice Department’s new corporate charging policy. The policy allows firms to avoid criminal charges if they self-report the violations, cooperate with the government and work to remediate compliance problems.

Officials expressed concerns because the company did not qualify for a deferred prosecution under the policy, and because such agreements were meant to be reserved for companies that tried to remedy compliance problems and cooperate in good faith, one of the sources added.

In the end, the Justice Department took no action against M-Class Mining itself, instead indicting four individuals who worked for the company with conspiring to defraud the government. Some also faced additional charges of falsifying records and obstruction.

An agreement to pause the statute of limitations expired at the end of October, making criminal charges against the corporation now impossible.

O’Callaghan declined to comment, and said the company also declined to comment.

Despite Woodward’s overall lack of enthusiasm on pursuing corporate criminal cases, some say they have appreciated his general willingness to advocate for prosecutors to move more quickly.

At the start of most meetings, in fact, he likes to remind people of how many days remain in the Trump administration, pushing them to get results, according to sources who have been in meetings with him.

“He likes to be viewed as a bear you don’t want to poke,” one person who worked closely with him said.

The “Stanley-only brief”

The No. 3 official at the Justice Department has historically drawn less attention than the attorney general and deputy attorney general, but Woodward has made headlines in ways his predecessors have not.

One of the most striking aspects of his tenure is his willingness to put his signature on a number of unusual and controversial legal filings that make many of his colleagues uncomfortable.

Earlier this year, Woodward was the sole DOJ signatory on a settlement between the president and the IRS which called for the creation of a $1.8 billion “anti-weaponization fund” that would be used to provide payouts to those who could show they had been wrongfully targeted by the government. It was widely seen as an effort to distribute money to Jan. 6 defendants and other Trump allies who had been investigated or charged under the Biden administration.

Woodward had represented several would-be claimants to the fund, a fact that prompted a federal judge in Florida to rebuke him in a scathing court ruling. The judge sent a copy of her opinion to the District of Columbia bar, where Woodward is licensed. A nonprofit watchdog group filed a separate bar complaint.

Gene Rossi, a defense attorney who worked closely with Woodward on a separate Oath Keepers trial, said he was “always professional and very gifted.”

“But am I disappointed in what he is doing today? Absolutely yes,” Rossi said. “My respect for Stanley Woodward really took a hit when he negotiated that IRS settlement … It was such an easy call ethically to recuse yourself.”

Woodward has recently drawn the ire of Judge Ana Reyes, who is overseeing the ongoing civil litigation over Mr. Trump’s plans to renovate East Potomac Golf Links in D.C.

On Oct. 16, Woodward was the sole signatory on a brief that accused the judge of bias and demanded she recuse herself from the case.

He also contended in a separate brief on Oct. 18 that the court had no jurisdiction on the case, saying the redesign of the golf course was not a “final agency action.” At a hearing the next day, Reyes asked other DOJ attorneys in the courtroom if they would be willing to refile the brief with their signatures on it, a request she later dropped.

Since then, Reyes has raised questions about whether government lawyers and officials intentionally misled her, and appointed a special master to help determine whether they engaged in misconduct.

The pleadings have privately embarrassed both political appointees and career attorneys in the Justice Department, and also baffled people who know Woodward well and have respect for him as an attorney, multiple sources with direct knowledge of the dynamic said. When Woodward is the sole signature on a brief, it is usually a safe bet that no one else in the department was willing to sign it, the people said.

“A Stanley-only brief is a sure sign that everyone else refused, or he knew everyone would refuse and didn’t even ask,” one of those people said.

In April, Woodward signed and submitted two briefs defending Mr. Trump’s plans to construct a new ballroom at the White House from a suit by a historic preservation group. Both included language that mimicked the style and tone of the president’s Truth Social posts. Attorney General Todd Blanche and Acting Deputy Attorney General Trent McCotter’s names also appeared on the briefs, which did not include any career officials.

“‘The National Trust for Historic Preservation’ is a beautiful name, but even their name is FAKE because when they add the words ‘in the United States’ to the National Trust for Historic Preservation, it makes it sound like a Governmental Agency, which it is not,” one of the filings said, accusing the group of “Trump Derangement Syndrome.”

One person who has worked with Woodward said that his willingness to sign certain filings is a sign of his leadership.

“He didn’t have to sign that brief. He easily could have ordered someone else to do it, but he recognizes that sometimes when you’re the leader, you need to be out in front taking the hits,” the person said.

A Justice Department spokesperson said that Woodward only signs briefs that he believes are righteous.

Woodward “doesn’t sign things he does not believe can be filed in good faith. He reads everything that he signs personally,” the spokesperson said, adding that “zealous advocacy should not be confused with ‘combativeness.’”

“Courts of appeals and the Supreme Court exist to affirm or overturn decisions of a lower court,” the spokesperson added.

The fact that the associate attorney general is signing briefs in court at all is a surprise to some veteran DOJ attorneys, who say it is not customary practice.

“I can’t think of a single case during either of my stints in the Civil Rights Division where the associate AG was the only person who signed a court filing,” said Pamela Karlan, a former principal deputy assistant attorney general who now teaches law at Stanford. “In fact, I can’t remember a case — outside of a couple of cases at the Supreme Court, maybe — where anyone from the associate attorney general’s office appeared on the briefing. And there were always career lawyers on every filing.”

The Antitrust Division

Another unusual aspect of Woodward’s tenure is the extent to which he is overseeing the Antitrust Division.

Last year, Woodward and Chad Mizelle, then Bondi’s chief of staff, fired two deputies of antitrust chief Abigail Slater after she pushed back on a settlement clearing Hewlett Packard Enterprise’s $14 billion acquisition of Juniper Networks. One of them, Roger Alford, later said in a speech that Woodward and Mizelle had “perverted justice” by letting “lawyers and influence peddlers” shape antitrust outcomes.

A Justice Department spokesperson declined to comment on Alford’s allegations, saying the department would not respond to “outlandish complaints” from a “disgruntled former employee.”

Slater herself was fired less than a year later amid continuing clashes with Woodward and Bondi’s offices over antitrust cases.

Before her ouster, Bondi and Woodward tried to keep her from attending a meeting of antitrust regulators under the Organisation for Economic Co-operation and Development, or OECD. The Antitrust Division’s assistant attorney general customarily attends such meetings, and in that case, Slater was the chair of the group’s competition committee.

Department leadership said the trip would violate its travel rules and cut off Slater’s credit cards while she was overseas, CBS News previously reported. Sources said she was staying in a government-approved hotel and flew to Paris on a commercial flight.

A Justice Department spokesperson said the attorney general — and not the associate attorney general — had the authority to approve or deny travel requests.

The acting assistant attorney general who followed her left in June. At the OECD’s next antitrust meeting, the department sent a lawyer who had worked in Woodward’s office, and not anyone from the Antitrust Division, to represent the DOJ, sources with direct knowledge of the arrangement said.

Now, without anyone left to serve as acting assistant attorney general of the Antitrust Division, Woodward has been left to serve as its de facto leader.

A Justice Department spokesperson confirmed that Woodward has been delegated the authorities of the assistant attorney general, though he is technically not serving in that role.

He has consolidated control. He’s now in charge of signing off on all administrative subpoenas, known as “civil investigative demands,” that the Justice Department uses to compel the production of documents, sources said. Having someone at his level signing off on all those documents is unprecedented, sources with knowledge of the division said, noting that such demands are required by statute to be approved by the assistant attorney general.

His insistence on signing off on other moves, including appellate decisions, has started to cause gridlock in the Antitrust Division, multiple sources said. Some people have resorted to bringing in books to read in the office because their work has slowed so much.

“He is exercising outsized power,” said one former official who is familiar with how the Antitrust Division is customarily run. Another source described the dynamics in a similar way.

“It’s just a desire to have control of all aspects of the division’s activities,” the person said.

But what some people see as micromanagement, others see as an example of an associate attorney general who, unlike his predecessors, has taken on a more proactive oversight function.

“Stanley is incredibly smart and deeply engaged. I don’t think there has ever been an associate attorney general that has ever been more engaged than Stanley,” said another person who has worked directly with Woodward.

A Justice Department spokesperson said that Woodward, as associate attorney general, has oversight authority of Antitrust and has been playing the role for over eight months.

“He has played an oversight and leadership role in ensuring affordability for all Americans with much of the operations and decisions of the Antitrust Division already requiring the Associate’s involvement and approval. The Associate Attorney General is best equipped to provide interim leadership over the Antitrust Division to ensure continuity and promised progress in protecting competition for American consumers,” the spokesperson added.

The art of Woodward’s deal

While Woodward has expressed disdain for corporate criminal cases, he has also demonstrated an eagerness to ratchet up the fines and penalties against corporations when it comes to civil enforcement matters.

In some cases, he has pushed DOJ attorneys in settlement talks to go back to a company and tell them that the government was increasing the amount of money that would be needed to resolve the case — an uncommon tactic.

“He can be pretty aggressive on the civil side,” one person told CBS News, adding that Woodward is viewed as “quirky and unpredictable.”

In some cases that could be potentially handled both criminally or civilly, Woodward has often advocated for civil resolutions.

“He fancies himself a savvy negotiator,” another person noted, saying there have been several occasions where Woodward has offered to obtain a high monetary penalty if lawyers working on the case would let him negotiate a civil resolution in lieu of a criminal one.

One such example played out with parallel criminal and civil investigations into the private equity giant KKR.

In January 2025, shortly before the Trump administration took office, the Justice Department filed a civil complaint alleging the company repeatedly made false statements and omitted key pieces of information at least 16 times in its pre-merger applications, known as Hart-Scott-Rodino filings.

Federal prosecutors in the Antitrust Division also believed the evidence was strong enough to pursue a separate criminal investigation, according to several sources familiar with the matter and a September 2024 corporate filing from KKR disclosing the receipt of a grand jury subpoena.

Initially, prosecutors got a green light from senior political appointees under the Trump administration to continue with the criminal investigation.

But Woodward opposed pursuing a criminal case, one of those sources said. Separately, one of KKR’s two chief executives separately complained to the White House about the case, two sources familiar with the matter told CBS News.

After that, prosecutors were ordered to drop the criminal probe before it ever got far enough to know whether charges could be warranted, one of the sources added.

In August, the Justice Department reached a civil settlement with the company for $250 million — an amount that the DOJ touted as being the “largest ever penalty” for violations of a law known as the Hart-Scott-Rodino Act.

Woodward lauded the settlement, saying in a statement that it sent “a powerful message” that the Justice Department is “committed to vigorous enforcement.”

KKR declined to comment beyond its prior statement, in which it said it had “agreed to a civil settlement that fully resolves the litigations and all open investigations by the Antitrust Division.”

“We strongly disagree with the Antitrust Division’s characterization of this matter. We believe that our firm acted in good faith at all times under our prior filing process, and that it was consistent with industry practice,” the company said.

Ironically, when Woodward made his first appearance at a press conference at the Justice Department as associate attorney general, it was to announce a superseding indictment in a corporate antitrust case involving several Chinese shipping container companies.

The indictment charged both individuals and the corporate entities, alleging they engaged in illegal price fixing during the pandemic.

“We are holding these Chinese bad actors accountable for exploiting the pandemic to fill their own coffers,” Woodward said at the time.

The indictment was originally returned in December 2025 — just about two months into Woodward’s tenure as associate attorney general.

Unlike some of the other corporate criminal cases, sources said the Chinese containers case did not draw any opposition from Woodward, who even joked that the staff had “snuck one past” him.