New York, NY — For years, Jerry Ashton has cultivated the image of a crusader. A former Navy journalist and co-founder of RIP Medical Debt, Ashton reinvents himself in the 2010s as a whistleblower exposing the predatory practices of the debt collection industry. He co-founds RIP, which goes on to abolish billions in medical debt, and builds his reputation as both an insider-turned-reformer and a media-savvy advocate.
By 2024, he launches End Veteran Debt (EVD), presented as a national, 50-state initiative to erase veterans’ financial burdens and reduce suicide. Ashton insists he has sacrificed a six-figure salary to lead the fight. To many donors and institutions, he looks like a patriot taking on one of the most pressing crises veterans face: debt and its deadly connection to despair.
But beneath the branding lies a contradiction. On October 24, 2025, Ashton mistakenly sends an email to veteran advocate and journalist Timothy Pena that was meant for his attorney. In it, Ashton admits he is “in the process of filing for bankruptcy,” scrambling to file three years of overdue tax returns, and battling collectors over debts owed to media figure Cary Harrison of The Cary Harrison Files podcast. For a man who has made his name promising to end debt for others, the revelation is staggering
The mistake exposes more than personal financial collapse. It validates Pena’s warnings, long dismissed by Ashton’s allies, about the credibility of End Veteran Debt. For two years, Pena has tried to raise alarms: that Ashton trivialized his PTSD, excluded him from public events, and refused to support reporting on dire conditions at the Borden Avenue Veterans Residence with MIlitary Veteans in Journalism of which both are members.
Rather than engage, Ashton maligned him. Veteran-serving officials—including those at the NYC Department of Veterans’ Services and Staten Island’s Military and Veterans Families Taskforce—began to distance themselves from Pena even as they welcomed Ashton into their circles
Central to Ashton’s rise in New York is his partnership with Michael Matthews, director of Staten Island’s Performing Provider System (PPS) and head of the SMVF Taskforce. Matthews promoted Ashton through newsletters, distributed EVD flyers, and co-hosted events like a Fordham University summit on suicide prevention.
When Pena asked tough questions about EVD’s transparency, Matthews called his advocacy actions, “inappropriate” and barred him from Taskforce meetings while Ashton pitched donors inside. The October 24 email undercuts Matthews’ denials of any knowledge of Ashton’s troubles, confirming that the partnership operated without the transparency veterans and donors deserved
The story that emerges is not just about Ashton’s personal bankruptcy. It is about how charisma, awards, and partnerships can mask hidden liabilities; how critics can be silenced in order to protect fundraising narratives; and how institutions fail when conflicts of interest go unchecked.
Debt is not an abstract crisis for veterans — it is directly tied to suicide risk, homelessness, and instability. When advocacy collapses under concealment, it is veterans who pay the price.
This exposé begins with Ashton’s public image as a debt crusader and traces the unraveling of that story, through the mistaken email that revealed his own bankruptcy, the gatekeeping of his business partner, and the silencing of a fellow veteran advocate. It is a story of credibility built on a fragile foundation — and a reminder of why accountability in veteran nonprofits is a matter of survival, not branding.