Early in his escalating war against the state Gaming Commission, Mayor Martin J. Walsh deployed a new weapon: a pricey outside lawyer who radiates intensity and in just 15 minutes managed to get under at least one commissioner’s skin.
The former prosecutor, Thomas C. Frongillo, forcefully told commissioners that part of their licensing process was backwards and at risk of a “legal error.”
The state’s top casino regulator, Steve Crosby, did not hide his irritation at the lawyer’s aggressive bedside manner.
“The right thing to do,” Crosby said in March 2014, “is to ignore some of the obnoxious rhetoric.”
Since then, Frongillo’s rhetoric has only gotten hotter. A lawsuit he filed on Walsh’s behalf flat-out accuses the five-member commission of law-breaking and corruption, which the gambling panel denies.
To the mayor, Frongillo is an “aggressive and highly accomplished litigator,” serving as a relentless advocate for Boston. But the city’s fierce — and expensive — court strategy against the commission has also raised eyebrows in legal circles and drawn rebukes from the judge in the case and the US attorney’s office.
Frongillo, 57, has the largest legal contract awarded by the Walsh administration, and has already been paid nearly $1.3 million in tax dollars in Boston’s casino dispute. The city pays him $490 an hour — more than double what outside lawyers generally make working for the city, according to a Globe review of contracts. Frongillo’s fee reflects a discount of roughly 50 percent from his regular rate.
In his three decades in the law business, Frongillo has amassed an impressive résumé that includes high-profile drug and organized crime cases as a federal prosecutor from 1990 to 1999, and, as a white collar criminal defense lawyer, an acquittal in the largest criminal environmental law case in US history.
In hiring Frongillo in February 2014, the city legal department also claimed that the litigator “has extensive experience in gaming law,” according to a memo explaining Frongillo’s no-bid contract written by the city’s chief lawyer, Eugene O’Flaherty.
The claim was not true — Frongillo had no prior experience in gambling law. The Walsh administration now defends the assertion by saying Frongillo is an expert in complex regulatory law and that “gaming law is a subcategory of regulatory law.”
Another area where Frongillo has experience is the State House, where O’Flaherty and Walsh served as legislators. During a dark period on Beacon Hill, when federal prosecutors investigated a rigged hiring system in the Probation Department, he gave free legal services to legislative leaders. He said then his firm was waiving fees “out of civic duty,” the Globe reported in late 2010. The lawyer and his household have donated $3,000 to Walsh’s campaign since 2013, records show.
The Walsh administration insists Frongillo’s pro bono work for lawmakers had nothing to do with his lucrative city contract, and said in a statement that Frongillo “did not provide representation to either Mayor Walsh or [O’Flaherty] during the probation investigation,” nor any other time.
Walsh’s connection to Frongillo came later, the administration says, when Walsh chaired the House Committee on Ethics. In 2013, Walsh hired Frongillo to investigate alleged improprieties by a lawmaker.
That was when Walsh saw the lawyer’s “tenacity” and “extensive legal knowledge” firsthand, the administration said. A year later, Walsh turned to Frongillo when he needed some legal firepower in Boston’s battle to gain more control over casino proposals on its borders.
Rebuffed by the gambling commission, Walsh turned Frongillo loose in court, suing the commission to overturn its selection of a Wynn Resorts project in Everett as the sole casino in Greater Boston. An expanded version of the suit asks for the disqualification of all five commissioners.
The aggressive tactics may have taken a toll. Superior Court Judge Janet L. Sanders, overseeing Boston’s lawsuit, chided the city for using litigation as a public relations tool. The office of US Attorney Carmen M. Ortiz admonished the city for what it described as a “vicious civil lawsuit” that “spewed and spun” rumors.
“What [Judge Sanders] is saying is, focus on the legal issues and less on the politics,” said former federal judge Nancy Gertner.
The Walsh administration defended its tactics. “We disagree with the characterization that there have been ‘public rebukes’ ” of the city’s legal strategy, the administration said.
Frongillo declined to comment for this story. His one-time boss, former US attorney Wayne Budd, recalled him as a “very reasonable prosecutor.” Another former boss, Donald K. Stern, who was US attorney for Massachusetts from 1993 to 2001, said Frongillo “is a hard-charging lawyer, very hard working, very well prepared, and very thorough.”
Frongillo, who grew up in Mansfield, worked summers at Filene’s while attending the College of the Holy Cross, where he played two years of football as a defensive back, graduating in 1979. He earned a law degree from the University of Virginia in 1982, according to his Massachusetts Bar application. Colleagues described Frongillo as an exhaustive researcher with a remarkable ability to distill mountains of information. A fellow lawyer recalled Frongillo running 40-yard wind sprints at dawn during a landmark trial, a workout that mirrored his intensity in the courtroom.
What may have been Frongillo’s most significant legal victory occurred 2,500 miles from Boston, in federal court in Missoula, Mont. He played a key role in winning an acquittal for Robert Bettacchi, one of several executives from chemical company W.R. Grace accused of contaminating a small mining town with asbestos. Hundreds of people died from asbestos-related diseases.
In the blockbuster 2009 case with scores of high-powered lawyers, Frongillo stood out, according to Andrew Schneider, a Pulitzer-Prize winning investigative reporter who broke the story about the mine and wrote the book “An Air That Kills.”
“He asked unbelievably penetrating questions,” Schneider recalled in an interview. “Some of his questions just startled the hell out of them and they were good, fair, appropriate questions. There was very little bomb throwing.”
Frongillo’s withering cross-examination of key government witnesses exposed fundamental holes in the prosecution, said Brian K. Gallik, a Montana attorney who shared the defense table with Frongillo.
“He’s stepped into a hornet’s nest here in Montana,” Gallik said. “There was a lot of political motivation to prosecute these people. He did an outstanding job. I know he had the respect of the court and the other lawyers.
“He’s very intense,” Gallik said. “If I needed a lawyer, I’d want him in my corner.”
John R. Ellement and Lisa Tuite of the Globe staff contributed to this report. Mark Arsenault can be reached at firstname.lastname@example.org. Follow him on Twitter @BostonGlobeMark. Andrew Ryan can be reached email@example.com. Follow him on Twitter @GlobeAndrewRyan.