Contender for top NYC City Hall post left trail of penalties and debt as a lobbyist

Before coming to City Hall, one of the top contenders to become Mayor Adams’ next chief of staff ran a lobbying firm that was fined often and repeatedly for failing to comply with lobbying disclosure requirements, a review of public records shows.

Tiffany Raspberry, who currently serves as a senior advisor for external affairs in Adams’ administration, is one of several names that’s come up in internal discussions about who will succeed Frank Carone, the mayor’s current chief of staff.

Carone plans to step down at the end of the year. Raspberry has served for the past several months as one of the mayor’s top advisors handling intergovernmental affairs.

Before her stint in City Hall, records show she worked as a lobbyist through her firm York Group Associates where she represented controversial clients such as tobacco giant Reynolds American Inc.; the scandal-plagued homeless services provider CORE Services Group; Camber Property Group, which co-owns the neglected Bronx housing complex where 17 people perished in a fire earlier this year; and Slate Property Group, which was at the center of the Rivington House scandal during former Mayor Bill de Blasio’s administration.

Records also reveal that those clients are still registered to lobby on both the city and state levels.

Raspberry says she hasn’t interacted with any past clients “in any professional matter” while working under Adams, but she’s also not required to formally disclose such interactions — thanks in part to Mayor Adams’ decision earlier this year to roll back a de Blasio policy requiring city officials disclose meetings with lobbyists.

Because the de Blasio policy was allowed to lapse, Raspberry and other top staffers are not required to disclose their meetings with lobbyists. And since joining the Adams’ administration, Raspberry has not disclosed any personal conflicts-of-interest policies regarding her specific portfolio of responsibilities.

When asked about her past experience representing clients as a lobbyist and how those relationships might influence her current work, Raspberry responded that the administration has “a strict firewall between past work and what we do in this office, which is why I have not interacted in any professional matter with past clients.”

“I will recuse myself from such matters as long as I work in this administration,” she said.

A source familiar with the policy, who spoke anonymously out of fear of political retribution, pointed out that the policy was created in the wake of several scandals to prevent self-dealing and to provide more transparency around lobbying activity.

“There’s a reason why they don’t want to do it,” the source said of Adams’ decision to roll back the policy.

The source then said that it’s unclear what that reason is, despite the contention from those in Adams’ administration that it was duplicative of already existing rules.

“That’s the problem,” the source said, adding that the lack of a better rationale for dumping the rule will only lead to critics calling into question the motives and actions of high-level staffers.

In Raspberry’s former life as a lobbyist, her firm failed to follow city and state disclosure requirements dozens of times between 2011 and 2020, leading to nearly $38,000 in fines levied by the city Clerk’s Office against her firm for late and incorrect filings.

For 2020 alone, Raspberry’s York Group was slapped with $3,750 for lobbying disclosure violations.

Those fines —and the fines for the years prior — have been paid in full, according to a spokesperson with the Clerk’s Office.

In 2018, a similar pattern of disclosure violations led the state’s Joint Commission on Public Ethics to issue a report and settlement agreement with Raspberry that said her firm “failed to timely file statements of registration, registration amendments, lobbyist bi-monthly reports, and other required documents, some of which were over six months late.”

That settlement, which Raspberry signed off on, shows she agreed to cough up more than $15,000 to address the violations. The agreement also states that $12,725 would be waived if she filed her lobbying disclosures on time for one year.

While it’s unclear whether she complied with that stipulation, it is clear from City Clerk’s Office records that in 2019, her firm once again was getting slapped with violations for filing late disclosures.

When asked about it, Raspberry chalked it up to bookkeeping mistakes and resorted to an explanation often employed by her boss — that she’s “perfectly imperfect.”

“Like every member of this administration, I hold myself to the highest standards, but as the mayor often says, I’m perfectly imperfect. I’ve worked to rectify any clerical mistakes I may have made in the past,” she said. “I built this business, my first, from scratch and, like many small business owners, made small mistakes along the way.”

[ NYC Mayor Adams’ chief of staff Frank Carone confirms he’s resigning, and top deputy Lorraine Grillo likely to follow: sources ]

Three months after JCOPE issued its settlement, Raspberry’s York Group sued that now defunct regulatory agency. In the lawsuit, York and its co-plaintiffs argued that JCOPE did not have the authority to implement reams of new lobbying regulations.

The plaintiffs argued that the new rules were a case of “bureaucratic overreach.” One of them was David Grandeau, a former state lobbying enforcement official turned lobbying-compliance lawyer who once described himself in an interview with Crain’s as the “dark prince of disclosure.”

In their complaint, the plaintiffs note that Raspberry’s firm “is required to file bimonthly disclosure reports,” but they took a tact different from Raspberry’s “perfectly imperfect” remark and omitted the fact that she failed to meet those obligations repeatedly. Ultimately, the lawsuit was settled in December of 2018, a month after it was filed.

While the Clerk’s Office noted that Raspberry has paid off her disclosure-related fines, records show that the York Group has not paid several liens issued against it by the state Department of Labor between 2017 and 2019 totaling more than $13,000.

Based on a review of public records, it is not entirely clear what those liens are connected with, but the records show that the York Group has only satisfied three out of 11 liens filed by the state.

As a member of Adams’ administration, Raspberry was required to file a financial disclosure form with the city’s Conflicts of Interest Board. On the 2021 form, she answered “yes” when asked if she owed “any entity or person (other than a relative) $5,000, excluding mortgages on your primary and secondary residences, or more for a period of 90 consecutive days during 2021 or on the date you file this report?”

But when prompted by the form to list the money she owes, Raspberry did not list the more than $13,000 in outstanding liens on York dated prior to 2020.

In a letter sent to Raspberry after the Daily News inquired about the liens, her lawyer Robert Feld said the liens stem from Raspberry’s payroll company failing to notify the state that York no longer had any payroll. He suggested that there’s “reasonable cause for abatement of the penalties.”

Raspberry said the payroll company’s mistakes stemmed from missing paperwork, “which I will file immediately.”