Errant Email Exposes End Veteran Debt Founder Bankruptcy and Collections

Timothy Pena • October 30, 2025

Staten Island Director of Veterans Services for Staten Island Military and Veterans Families (SMVF) Taskforce and Business Partner Claims He Was Unaware 

New York, NY -- A nonprofit dedicated to ending veteran debt is scaling back fundraising after its founder, Jerry Ashton, inadvertently sent an email admitting to bankruptcy and years of unfiled taxes to Timothy Pena, a veteran advocate and fellow journalist. The misdirected email has not only shaken the credibility of End Veteran Debt (EVD)—a charity Ashton launched in 2024—but has also exposed internal fractures within its partnership with Staten Island’s Performing Provider System (SI PPS) and its director, Michael Matthews.

The October 24, 2025 email, intended for Ashton’s attorney, described a tense call with the Long Island law firm Smith Carroad Wan & Parikh over unpaid debts tied to Ashton’s failed media venture, Let’s Rethink This. In it, Ashton admitted he was “in the process of filing for bankruptcy” and catching up on “three years of tax filings.” He added that his own attorney had apparently dropped him as a client before asking, “What next, coach?” — believing Pena to be his lawyer.

For Pena, the accidental disclosure confirmed what he had long suspected: that EVD’s leadership lacked the transparency and accountability expected of a veteran-serving nonprofit.

Ashton’s bankruptcy revelation came just weeks after Pena was barred from the Staten Island Military and Veterans Families (SMVF) Taskforce meeting, which Matthews oversees. Pena had objected to a proposed collaboration between EVD and the American Foundation for Suicide Prevention (AFSP). In a September 29 letter to AFSP, Pena warned that Ashton had ridiculed his service-connected PTSD and excluded him from a suicide prevention summit at Fordham University despite confirming him as a panelist. “Veteran suicide is not something to exploit to promote a funding scheme,” Pena wrote. “Vulnerable veterans place dependency on organizations like these in different ways—and Jerry doesn’t realize that.”

The Fordham event, Righting Veteran Wrongs, Ending Veteran Suicide, was heavily promoted through SI PPS newsletters and emails. The partnership touted a goal of forgiving $1 million in veteran debt through EVD’s “Operation Debt-Day” campaign. Ashton, a Navy veteran and former co-founder of RIP Medical Debt, was spotlighted as a national whistleblower and reformer. The Staten Island campaign promised to raise $15,000 locally to “support the Staten Island Veteran and Active Duty Community”.

But Pena, also a member of Military Veterans in Journalism (MVJ) like Ashton, began questioning how the organization would actually identify and assist indebted veterans. In a series of emails, he pressed Matthews for answers about EVD’s debt-purchasing practices. Matthews responded that EVD worked with ForgiveCo, a for-profit intermediary that buys and retires debt in bulk, and acknowledged that “the VA debt actually is not available for purchase.” He further conceded that EVD “cannot forgive individual debt” and that the organization does not even know who benefits until after portfolios are purchased.

For Pena, this was proof of a misleading public message. “End Veteran Debt gives the impression that you can have my debt forgiven, which is not the case,” he wrote to Matthews. “This is more about purchasing VA debt and less about the regular veteran whose credit score is in the toilet”.

When the bankruptcy email surfaced days later, Pena forwarded it to Matthews, seeking an explanation. Matthews replied that he “had no prior knowledge” of Ashton’s financial troubles but later wrote that “Jerry will be scaling back his fundraising efforts.” Matthews offered no clarification on whether donors were to be informed or whether SI PPS has plans to review the partnership.


The email misfire also raises broader ethical questions. Ashton’s public persona as a debt abolitionist stands in sharp contrast to his private financial collapse. Over the summer, he had received the Pillar Award at the Whistleblower Summit and Film Festival for his work in debt reform. At the time, he was lauded by SI PPS as a “truth-teller” and “leader in veteran reform”—even as he was negotiating with creditors and preparing for bankruptcy. 


Text messages from July show Pena confronting Ashton over his lack of support for Pena’s own whistleblower case of “misconduct and misappropriation of federal funds,” with the Veterans Affairs Grant and Per Diem program to which Ashton responded, “That’s your work, Tim,”  texting, “Debt is my world, whether civilian or veteran. I’m sorry you don’t respect that.” 


If Ashton harbored resentments about Pena’s concerns, he never voiced them. He personally scheduled Pena to lead a roundtable and moderate the opening panel, “Field Experience,”—a session focused on veteran incarceration, homelessness, and debt—only to abruptly remove him from the lineup less than 24 hours before the summit. 


The decision blindsided Pena and came without explanation or warning, effectively erasing a veteran voice from an event marketed as empowering those very perspectives.


Despite Ashton’s promise in an email to “remedy my mistakes,” the damage was done. “For the first time since coming to New York City, I woke up the next morning overwhelmed by betrayal and suicidal thoughts,” Pena wrote in his letter to AFSP. “This is what happens when non-veterans profit from veteran suffering.”


As of late October, SI PPS has not issued a public statement addressing Ashton’s bankruptcy or clarifying the financial status of the End Veteran Debt initiative. Matthews has said only that discussions are underway to “evaluate next steps.”


Meanwhile, the controversy has cast a long shadow over what was billed as a groundbreaking “Civ-Vet” partnership between civilians and veterans. Instead, it now serves as a cautionary tale about the dangers of unchecked trust in charismatic nonprofit leaders and the urgent need for stronger financial oversight within the veteran services sector.


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Timothy Pena is a service-connected disabled Navy veteran living with PTSD and has chronicled his transition into the New York City while also advocating for better treatment of other veterans in transition. He has written extensively about his experiences with mental health and suicide ideation, homelessness, and the judicial system. Because of his mental health struggles, Pena often relies on ChatGPT for his writing but maintains all his opinions are his.