The Cruelty is the Point

Matthew G. Saroff
5 min readJun 3, 2022

It turns out that Donald Trump’s inspector general for Social Security set up an administrative kangaroo court to harass poor people receiving benefits.

It sounds like she was doing this just because hurting the poors amused her, as did retaliating against employees of her department who noted that her actions were unlawful:

Four years after her longtime partner died of kidney cancer, federal agents knocked on Gail Deckman’s door outside Chicago and told her she was in trouble: She had kept thousands of dollars in Social Security disability benefits that should have stopped when he died.

Deckman told the agents she thought the $1,400 check deposited each month into an account to which she had access was a payment for land her partner had sold in Michigan. She spent the money on rent and clothes and gifts for her grandchildren, she said.

The inspector general’s office, which investigates disability fraud and tries to recoup money for the government, ultimately charged her $119,392 — nearly three times what she received in error.


The inflated fees were set in motion during the Trump administration, when attorneys in charge of a little-known anti-fraud program run by the inspector general’s office levied unprecedented fines against Deckman and more than 100 other beneficiaries without due process, according to interviews, documents and sworn testimony before an administrative law judge. In doing so, they disregarded regulations and deviated from how the program had recovered money since its inception in 1995, failing to take into account someone’s financial state, their age, their intentions and level of remorse, among other factors.

The sums demanded by the government stunned those accused of fraud. The unusual penalties were not the only break with how the Civil Monetary Penalty program had previously been conducted: Unlike in the past, the chief counsel also directed staff attorneys to charge those affected as much as twice the money they had received in error, on top of the fines, interviews and court testimony show.

The escalating penalties created a giant jump — at least on paper — in the amount of money the inspector general could show lawmakers it was bringing in, according to interviews and sworn testimony obtained by The Washington Post. Fines as high as hundreds of thousands of dollars were imposed on poor, disabled and elderly people, many of whom had no hope of ever being able to pay.

A Chicago woman was fined $132,000 after wrongly receiving as much as $10,618 in benefits, according to internal data of penalties and assessments obtained by The Post. A Denver woman was sanctioned $168,000 after cashing as much as $14,960 in wrongly received checks. A New Jersey woman is on the hook for nearly $435,000 after she accepted about $47,000 in benefits but failed to report a $120,000 house she inherited from her father and car loans she co-signed for her children, on what she said was a lawyer’s advice.


The remarkable penalties led to tumult inside the Office of Inspector General Gail Ennis, where a whistleblower was targeted for retaliation, according to a ruling this month by the administrative judge at the Merit Systems Protection Board.

Ennis, who was sworn in as a Trump appointee in January 2019, declined an interview request but said in a written statement that her office is “unaware of any basis that supports the statement that unprecedented fines have been imposed.”


Inside Ennis’s office, two officials raised concerns about the fees to her and her top staff, according to interviews and court testimony: Deborah Shaw, considered the program’s most knowledgeable, experienced attorney, who testified in September that she was directed by her bosses to issue penalties she found unconscionable; and veteran senior executive Joscelyn Funnié.

Ennis told them that she would not renegotiate any cases because she did not want to draw attention to the program and worried that Social Security would take it away from her office, according to testimony and four people familiar with her comments during a staff meeting.

After they repeatedly pressed to have cases reexamined and the penalties lowered, Shaw and Funnié were escorted out of the agency’s headquarters in Woodlawn, Md., in September 2019 and placed on paid leave. Ennis then fired Funnié, who had also raised separate concerns to her about what she believed were improper hiring actions she took and directed that Shaw, who was also threatened with suspension, be demoted, according to hearing transcripts and people familiar with their cases.

In a May 6 ruling, Judge Craig A. Berg found that Shaw was the victim of a “prima facie case of whistleblower reprisal” by Ennis’s office and ordered the agency to restore back pay and benefits and reinstate her as a supervisor.

Shaw “has shown that she had a reasonable belief she was disclosing an abuse of authority when she raised issues with the drastic increase in penalties the [Civil Monetary Penalty] program was assessing …” Berg wrote in a 68-page decision. He found “significant evidence” that Ennis and her top staff “had motive to retaliate” against Shaw as she became a “vocal advocate” to reopen 83 cases whose penalties she believed were excessive.



Ennis, a former WilmerHale attorney, also wrote that the number of audits “does not sufficiently capture the value the OIG provides to taxpayers” and said her office’s productivity has remained consistently above the average for the federal watchdog community.

WilmerHale is a white show law firm, with a lot of political folks, Robert Mueller, Charlene Barshefsky, C. Boyden Gray, and Ken Salazar come to mind, going through its revolving doors.

They do a lot of lobbying, and Ennis is a big Trump donor, so mindless cruelty toward the powerless, and retaliation against employees who report wrong doing, is par for the course.