On the day he took over City Hall, a record-setting 20 years ago, Thomas M. Menino was accompanied by a retired FBI agent and Norwood selectman who had quietly become one of the best friends Menino would ever have.
Menino described his graying, square-jawed companion that day as “my second father, really,” and he wasn’t exaggerating. The two men had forged an enduring bond, filling a need for both: John F. Kinnaly and his wife were childless, and Menino’s father, Carl, had died in 1989.
But the relationship between the two men would eventually become a headache for the mayor in ways that neither man could have foreseen.
It began in 2011, with Kinnaly’s death at age 85, and his last will and testament. In a singular act of generosity, Kinnaly had left the mayor his entire estate, including the golf course condominium in Palm Beach Gardens, Fla., where he had retired.
“He always said, ‘When I die, you’ll own this place,’ ” Menino said, describing the condo as a “beautiful place,” situated on a corner lot.
Yet, through 2011 and most of 2012, as Kinnaly’s estate was being settled and the mayor was shouldering the daily crises associated with running a major American city, Menino never publicly mentioned his old friend’s unusual legacy.
Recently, however, word of his inheritance — and the names of City Hall insiders who helped Menino move Kinnaly’s case through the complex probate process — made its way into Boston development circles, spurring a rumor the Florida bequest could be a payoff to Menino for favorable development decisions here.
But now, in his first public remarks on Kinnaly’s last will and testament, Menino is saying what documents in the Kinnaly case also make clear: Kinnaly’s generous gift was, in the end, a mirage. He left behind next to nothing to inherit.
“No one made money on this one,” the mayor said in a recent interview in his fifth-floor City Hall office. “It cost me money, but I don’t worry about it. He was a friend.”
Menino said he was uneasy about the inheritance since the day in 2006 when Kinnaly named him his sole heir. But not because of how it might look or the political questions it might raise.
“I thought it was nice, but I worried about condo fees and who was going to live there,” Menino said. “It didn’t excite me, but I said I was grateful, of course.”
Menino said he tried to look on the bright side, figuring he would be able to offer his son and daughter a place to take a winter vacation at a condo where Menino had been a regular visitor since Kinnaly bought the place in the 1980s.
But when Kinnaly died of cancer in April 2011, Menino’s qualms proved justified. Kinnaly, never shrewd with money, had taken out a reverse mortgage and run up a real estate debt greater than the condo’s value, meaning it would soon fall into the hands of creditors.
And when Menino turned to another old friend to help settle Kinnaly’s estate — influential Boston real estate lawyer Henry G. Kara — he sparked speculation that Kinnaly’s bequest, and the management of his probate case, might have been an attempt to curry favor with a mayor who holds extraordinary sway over development decisions in Boston.
“I said, ‘Henry, what the hell do I do?’ ” Menino recalled.
Kara, ever the loyal friend, quietly took charge of the matter, and was one of several Menino insiders who played a role in the case, either helping the mayor or seeking reimbursement for their expenses for the help they gave Kinnaly.
They included Herbert “Herbie” Hoffman, a former Boston businessman and an old Menino acquaintance who acted as Menino’s representative in Florida, and John E. Kavanagh III, another old Menino acquaintance recently awarded development rights in Charlestown and the city’s booming Innovation District, who paid some of Kinnaly’s last medical bills.
Kavanagh’s name, in particular, raised eyebrows among some who wondered whether he might have been rewarded developments rights because he had come to the aid of the mayor’s “second father.”
But Menino, who is sensitive about criticism that he plays favorites among Boston developers, said he turned to Kara only because he’s a friend and never lobbied the Boston Redevelopment Authority, which he controls, on Kavanagh’s behalf.
The true story of the inheritance-that-never-was, he said, is simply a tale of an extraordinary friendship that took an unusual turn along the way.
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As an FBI agent, Kinnaly helped investigate the Plymouth mail robbery of the early 1960s, then the largest cash heist in US history. With his late wife, Louise, he owned Norwood Tool and Industrial Supply. And for 15 years, from 1980 to 1995, he served on the Norwood Board of Selectmen.
It was while serving as a selectman in the early 1980s, when Menino was working as an aide to then-State Senator Joseph F. Timilty, that Kinnaly and Menino made their friendship — one that would be marked by frequent visits and daily phone calls virtually until the day Kinnaly died.
“John Kinnaly and Tom Menino literally loved each other,” said John J. Carroll, the longtime Norwood town manager. “It was absolutely an amazing relationship between the two of them.”
At the time, Norwood was eyeing the Norwood Armory, hoping to acquire the underutilized facility and convert it into a civic center, Carroll said. Timilty, whose district included the town, had agreed to sponsor legislation that would allow the town to seize the facility.
But there was resistance to the idea, Carroll said, and Menino and Kinnaly, who was friendly with then-governor Edward J. King, worked together behind the scenes to help the town realize its goal.
Menino told much the same story, adding, “I became a son and he was like a father to me.”
By the time Kinnaly died, it was clear that Menino and his wife, Angela, were the most important people in the world to him. His death notice describes him as a “dear friend” and shows he had no remaining close relatives. And in his last will and testament Kinnaly left all that he had to Menino, and named the mayor executor of his estate.
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Menino said he was not entirely surprised when he learned that he would not be inheriting Kinnaly’s condo — or much of anything else.
Kinnaly, Menino said, had a habit of picking up the tab at dinner and a penchant for donating to an increasing number of charities. “I used to yell at him all the time. I’d say, ‘John, you’re on a fixed income!’ ’’ Menino recalled.
And Menino knew Kinnaly had a history of being less than attentive to business dealings.
As an example, Menino said, Kinnaly never made an effort to collect a debt of about $1 million after the buyer of his industrial supply company told him he was having financial problems.
“Imagine a guy stiffing you for a million, and you don’t go after the guy?” Menino said.
At one point during the settlement of Kinnaly’s estate, Menino said, he heard from a woman who is perhaps Kinnaly’s only surviving relative, a sister-in-law whom Kinnaly had not seen or heard from in many years. “She called me up and asked if there was any money for her,” Menino recalled.
By that time, Menino had learned that Kinnaly’s years of living in Florida as a soft touch had wiped out his estate. Indeed, it was in 2007, only a year after Kinnaly willed his home to Menino, that he took out a reverse mortgage capped at $450,000, leading to a debt that neither he nor his estate would ever be able to fully repay.
As a result, the Federal National Mortgage Association, better known as Fannie Mae, took control of the property and eventually sold it to a couple from Canada for $185,000, dashing whatever thoughts Menino may have had about offering his son and daughter a chance to spend a carefree winter vacation.
Instead, the mayor dug into his own pocket to pay for a burial plot in Norwood’s Highland Cemetery, and laid his old friend to rest.
Now, in the final months of his long mayoralty, whenever he goes to work in the fifth-floor office with the stunning view of Quincy Market, he sits in a chair that Kinnaly bought for him after a memorable day in 1993 when, like a proud father, Kinnaly accompanied him to City Hall on his first day as acting mayor and found the desk chair wanting.
“That’s the kind of guy he was,” Menino said. “Generous to a fault.”Globe correspondent Ben Wolford contributed to this report. Michael Rezendes can be reached at firstname.lastname@example.org. Follow him on Twitter @RezGlobe.