💥New Chapter 11 Bankruptcy Filing - Trajector Holdings LLC💥
Dispute between owners pushes benefits program biz into chapter 11
On July 23, 2026, Trajector Holdings LLC (“holdco”) and twenty-one affiliates (collectively, together with holdco, the “debtors”) filed chapter 11 bankruptcy cases in the Middle District of Florida (Judge Brown). Founded in ‘14 by James Hill, II, Gina Uribe, and Richard Blaser, the debtors attempt to help clients “… understand, access, and navigate …” the US’s convoluted benefits programs. Their two principal businesses focus on programs under the U.S. Department of Veterans Affairs (the “VA business”), where they help ensure vets “… have complete and credible medical evidence …” for their applications, and the Social Security Administration (the “SSA business”), where it’s typically more straightforward: eligibility verification, paperwork, filing claims, yada yada yada.
The debtors are in chapter 11 because Mr. Hill and Ms. Uribe — each of whom owns ~44.67% of the company — don’t play well in the sandbox any more. You see, the holdco LLC agreement gives Ms. Uribe decision-making authority over “… technical medical consulting operations …” and Mr. Hill gets it over everything else. A spat arose about the delineation, and while the debtors thought they worked it out in August ‘24 via an addendum, surprise, they didn’t. It arose anew in early ‘26. Which maybe would’ve been fine if the debtors weren’t preoccupied with refinancing a ~$62.9mm, Deutsche Bank AG New York Branch (“DBAG”)-agented facility. But they were, 😔.
Delaware litigation for clarification ensued in May ‘26, and yes, technically, the company and Mr. Hill carried the day, but lack of agreement with their lenders — as well as the filing of two putative class actions in ‘26 alleging the VA business, which isn’t accredited, unlawfully charges fees “… for assisting with the preparation, presentation, and prosecution of VA disability claims,”* — made that victory Pyrrhic.
So chapter 11 it is — good, LOL, to see Mr. Hill and Ms. Uribe could agree on that. To get that process underway, the court held the first day hearing on July 24, 2026, where it granted all requested relief, and scheduled the second day hearing for August 17, 2026 at 11am ET.
The debtors are represented by Berger Singerman LLP (Jordi Guso, Clay Roberts, Edward Peterson) as legal counsel and Michael Moecker & Associates (Mark Healy) as financial advisor and CRO. DBAG is represented by White & Case LLP (Andrew Zatz, Kristin Schultz, Clint Simkins) and Smith Hulsey & Busey (John Thomas, Allan Wulbern, Carli Frederick) as legal counsel. Mr. Hill and his related entities — Blackfin Capital, LLC and Turner Raymond & Associates LLC — are represented by Burr & Forman LLP (J. Ellsworth Summers Jr.) as legal counsel.
*The debtors dispute the class actions, arguing they only create medical evidence. Think that’s right? It probably doesn’t matter. Many states have enacted, or are enacting, legislation similar to the state law cited in the two pending suits, so the business is likely dead any which way you cut it.
Company Professionals:
Legal: Berger Singerman LLP (Jordi Guso, Clay Roberts, Edward Peterson)
Financial Advisor/CRO: Michael Moecker & Associates (Mark Healy)
Claims Agent: Verita (Click here for free docket access)
Other Parties in Interest:
Prepetition Agent: Deutsche Bank AG New York Branch
Legal: White & Case LLP (Andrew Zatz, Kristin Schultz, Clint Simkins) and Smith Hulsey & Busey (John Thomas, Allan Wulbern, Carli Frederick)
Equity Owner: James S. Hill, II, Blackfin Capital, LLC and Turner Raymond & Associates LLC
Legal: Burr & Forman LLP (J. Ellsworth Summers Jr.)