After 14-year Absence, a City Attorney Reflects on What’s Changed


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STAMFORD – Members of the Board of Representatives who wanted to learn more about how the new city attorney will run his office got to ask an unusual question.

It’s because the attorney, Tom Cassone, is new for the second time.

Cassone was for 12 years chief legal counsel for Dan Malloy, Stamford’s longest-serving mayor, who held that office for 14 years and went on to serve two terms as governor. 

Cassone last headed the Stamford Office of Legal Affairs in 2009, returning in March after Mayor Caroline Simmons asked him to take the spot after the former lead attorney resigned.

During a meeting of the board’s Legislative & Rules Committee, the chair, city Rep. Phil Berns, himself an attorney, asked Cassone to draw a then-and-now comparison.

“What are two differences you see in the department today versus 14 years ago?” Berns asked.

Cassone had a quick answer. It referenced one of the innumerable effects of the COVID-19 pandemic. 

“The major difference is remote work and remote hearings,” Cassone said. “I’m not a fan of either. I think people get along better when they’re face to face.”

It’s evident when parties seek to settle disputes, he said.

“In settlement discussions, you search for a compromise among different points of view,” Cassone said. “It’s very difficult to get there when somebody can mute themselves, take themselves off camera, basically walk away.”

The technology enables the impulse, he said.

“It’s very hard to be harsh to somebody when you’re face to face,” Cassone said. “So I’m a big fan of being in person.”

The second difference between now and 2009 is the amount of city legal work that’s out-sourced, Cassone said.

“We rely a lot more on outside counsel than we did when I was corporation counsel 14 years ago,” he said. “There are a lot more specialties in law – that’s probably one of the main driving forces of that.”

During this year’s budget season – which began when the mayor proposed a spending plan in early March and ends May 15 with the setting of the mill rate – Casssone presented details of his department’s finances.

They show that the department budgeted $878,000 for outside counsel but in fact spent $1.1 million, according to the presentation. That’s $222,000 over budget.

The city hired outside attorneys to handle employee claims,  special investigations, out-of-state legal matters, land-use enforcement, labor negotiations, and other matters, the information shows. 

It’s not a new thing to overspend on outside counsel, according to the presentation, which states, “Actual expense has exceeded approved budget four of the last five years.”

The information shows that Stamford, the state’s second-largest city, is not out of line with spending on outside attorneys compared with Bridgeport, which ranks first in population; New Haven, which ranks third; and Hartford, ranked fourth. 

The number of Stamford on-staff attorneys is also in line with sister cities, according to the presentation. Stamford has 10 attorneys plus one part-timer, and a total of 15 people on staff, including paralegals and an executive assistant.

New Haven, a slightly smaller city, has 12 attorneys and a staff of 20, according to the presentation.

Cassone, who earns $184,000 a year, oversees the legal office, which is seeking a $3.8 million budget for the upcoming fiscal year, and the 14-employee Human Resources Department, which is seeking $3.3 million.

Attorneys in the Office of Legal Affairs represent the city, its employees, boards and commissions and their members in litigation. They negotiate contracts and purchase orders. They advise boards and commissions on procedures, ethics, and compliance with state law, the city Charter and Freedom of Information law. They negotiate real estate transactions, draft ordinances, defend the city in tax appeals, school matters, and more.

“We are the city’s lawyers and the Board of Education’s lawyers at the same time,” Cassone said. “We don’t go looking for business … it finds us.”

One of the more complex cases for Cassone’s office is in court now. Gaia Real Estate of New York has filed a 75-page, 15-count lawsuit against developer Building & Land Technology, its contractors, and the city, alleging they are responsible for a collapsing 225-unit luxury apartment building in Harbor Point called The Lofts.

Tenants were forced to vacate The Lofts last year because walls, ceilings and beams were cracking, floors were buckling, and doors and windows were popping out of their crooked frames as the building shifted on a failing foundation of wooden pilings. 

Attorneys for Gaia Real Estate, which bought The Lofts from BLT, allege that city crews failed to maintain underground infrastructure, and city building inspectors failed to require testing of the foundation.

Among the cases that tend to not make headlines, Cassone’s office handles slip-and-fall claims, pothole damage claims, and tax and zoning appeals; and issues hundreds of legal opinions requested by elected officials and city employees.

“We have a cornucopia of legal work,” Cassone told city representatives. “That’s what makes it fun for us on one hand and, on the other hand, makes it a challenge.”

Besides working remotely and hiring more outside attorneys, the tasks of the office are remarkably the same today as 14 years ago, Cassone said.

“I have found that a lot of stuff recirculates,” he said. 

The board, for example, recently passed a resolution to phase in the state-mandated property revaluation over two years. The resolution returned before the board Monday with a minor amendment requested by the state Office of Policy & Management, Cassone said.

“In 2004 we phased in a property revaluation and we used the same resolution. The statute was exactly the same – OPM just wanted a little different verbiage this time,” Cassone said. “Personalities change, interpretations change. But the law doesn’t change that much.”

Angela Carella

For 36 years prior to joining the Connecticut Examiner, Angela Carella was a beat reporter, investigative reporter, editor and columnist for the Stamford Advocate. Carella reports on Stamford and Fairfield County. T: 203 722 6811.