'9-Year Squatter' Cost NYC Landlord His Daughter's College Fund — Calls Court Fight A 'Twilight Zone Marathon'

For nearly a decade, Brooklyn landlord Thomas Diana says he has been trapped in a legal battle that continues to drain his finances and disrupt his family's future plans.

What began as a tenancy dispute in a small eight-unit building in Park Slope has evolved into years of court hearings, legal arguments, and delays. Diana claims the case has cost him up to $325,000 in unpaid rent and related losses, forcing his family to borrow money for his daughter's university education. Speaking to Fox News Digital, Diana described the ongoing dispute as a 'Twilight Zone marathon'.

A Legal Battle Stretching Across a Decade

Court records show the dispute dates back to 2014 when a woman moved into one of Diana's apartments after responding to a Craigslist advertisement seeking a live-in companion for an elderly, disabled tenant. The elderly tenant later died in 2016. Following the death, disagreements emerged over the occupant's tenancy rights, rent obligations, and whether the apartment remained protected under New York's rent-stabilisation laws. The dispute has since moved through multiple court proceedings.

According to Diana, the case has repeatedly been delayed. 'This has gone on for nine years. Nothing about this is justice,' he told Fox News Digital. 'Every time the case gets close to resolution, there's another delay, another lawyer change, another new story.'

Diana said the tenant has changed legal representation several times during the proceedings, contributing to what he views as an increasingly prolonged dispute.

Financial Impact on a Small Landlord

Diana says the financial consequences have been severe. He estimates unpaid rent and associated costs now total between $275,000 and $325,000. Unlike large property companies with extensive portfolios, Diana says small landlords can struggle to absorb prolonged financial losses from a single unit.

The situation, he says, has directly affected his family. 'It drained my daughter's college fund,' Diana said.

'Now we're borrowing money to pay for college while this just keeps dragging on.' He added that losing rental income from one apartment in an eight-unit building can eliminate any profit generated by the property. The financial strain eventually led him to launch a fundraising campaign online to help manage expenses linked to the case.

Tenant's Legal Team Rejects Claims

Attorneys representing the tenant strongly disagree with Diana's description of events. Casey Gilfoil, an attorney with Brooklyn Legal Services, told Fox News Digital that Diana's characterisation of the dispute does not reflect the court's findings.

'Mr. Diana's distortion of the facts in this case is a sad attempt to harass our client out of her rent-stabilised apartment, and he will not be successful,' Gilfoil said.

According to the tenant's legal team, a judge ruled that the apartment had been improperly removed from rent-stabilisation protections. They say the remaining issue before the court involves determining the legal rent and any damages that may be owed. Brooklyn Legal Services also said the tenant has money set aside in escrow pending a final ruling. Diana disputes that account.

He maintains that the court did not find he committed fraud and says he followed guidance provided regarding the apartment's regulatory status. 'The judge ruled there was no fraud,' Diana told Fox News Digital. 'She said I incorrectly destabilised the apartment. I did it as they told me to.'

Disagreements Continue Over Rent and Payments

Court stipulations previously required the occupant to make monthly use-and-occupancy payments while the dispute continued. Diana says those payments stopped years ago. He also disputes claims that sufficient funds have been saved in escrow to cover years of disputed rent.

The tenant, according to deposition testimony cited in the Fox News report, stated she has not worked full time for several years and has limited income. The two sides continue to disagree over key aspects of the case, including rent calculations, tenancy rights, and financial obligations.

Delays Remain a Source of Frustration

For Diana, one of the most difficult aspects of the dispute has been the length of time required to reach a final resolution. He says the continuing delays have made it difficult to plan financially and maintain the building. 'Judges talk in terms of months. They don't talk about what $300,000 actually does to a family,' he said. Diana also criticised housing inspections and administrative requirements that he believes have increased costs during the proceedings.

The case was adjourned again in April, extending the dispute into its tenth year. For now, the matter remains before the courts. Both sides continue to dispute key facts and legal interpretations, and no final resolution has yet been reached.