NORTHAMPTON — Bob Cahillane’s lifelong ties to the United States Navy, including a recently-wrapped 15-year stint as the area’s Blue and Gold Officer, may never have happened were it not for the “pissing match” he got into with his dad, the late “Big” Jim Cahillane, then mayor of Northampton.

“They had in the 1950s what were called low-profile tires, and if you went around a curb a little too fast the tires would squeal,” Bob explains.

He squealed them pretty good one day rounding the corner of Fruit and Old South where Officer Shea of the Northampton PD resided. “By the time I got home the old man was chewing on a bit to give me hell for speeding. I said ‘Screw it, I’m outta here!’”

Though the headstrong teen was ready to join the Navy right then and there, he was held back for a special public relations stunt, where 100 recruits from western Massachusetts and Connecticut would be inducted July 4 at the Big E.

“It was admirals, all kinds of brass, Eddie Boland — and the old man’s lecturing me on the way down about the evils of drink,” laughed Bob Cahillane, now 88, holding forth from his porch office at the side of the house. His “Rogue’s Gallery” fills one wall, black and white shots of personal heroes he’s spent time with: Tip O’Neill, John McCain, then-Sen. John F. Kennedy smiling with then-Mayor Cahillane in front of this very house.

Anyway, the lad was shipped off to a base in San Diego, where his immediate success floored him. “I struggled in high school but in the military I could figure things out,” he said, something that caught the eye of his commanding officer: “‘I’ve just been named provost marshal of this base and you’re my new assistant.’ I was all of 18.”

“Consequently, everything that happened on the base crossed my desk, so everybody wanted to be my friend,” he said, acutely aware that he’d also inherited a flair for politics, of the behind-the-scenes variety.

Annapolis

But if you’re from these parts and have thought about a career in the Navy or Marines via the U.S. Naval Academy in Annapolis, Maryland, the friend you needed to make was one Robert P. Cahillane himself, who’d make the trek to your family home in the Hilltowns, or meet you at Fitzwillys, where he’d assess your potential for leadership, and then push like hell.

The Academy, sort of a four-year college in uniform, comes without traditional tuition. A grad starts his or her naval career as a Navy ensign or a second lieutenant in the Marines. They then owe five years of service at a minimum. The first guy Bob shepherded through was Jimmy Aylward of Westfield. “I once asked him: ‘What are your better accomplishments?’ He said: ‘I can shut down and start up a nuclear reactor.’”

Reached by phone, Aylward laughed. “I have done that in the past. I honestly can’t say I’d remember how to do it now.”

Aylward was a southpaw pitcher for Westfield High when he met Bob Cahillane.

“I always wanted to serve,” said Aylward, now 35. “My dad was an Air Force pilot, my grandfather was a Navy pilot.”

With his grades, he had some options, collegewise, and was in D.C. with his dad, Jim, looking at Georgetown. Both knew that Annapolis was not that far and off they went. “I fell in love with the place,” said Jimmy Aylward. “Annapolis has a Northampton-on-the-water feel.”

Next step: reach out to a Blue and Gold Officer.

He said his mom, Noreen, had reservations over her son joining the armed services. “Bob was the deciding factor,” said Aylward. “Mom is Irish Catholic. They bonded.”

“I left for Annapolis after losing the state final to BC High,” he said. “I didn’t make the Navy team but played a lot of intramural.”

He was bitten by the submarine bug in his plebe year and focused his career on the nuke-powered vessels. “Lot of intelligent people in that community,” said Aylward, who served seven years of active duty, including two at the Pentagon. Then he earned a degree in business at Harvard, and is now a general partner in a major investment firm.

“Bob saw my potential early on and changed my life,” said Aylward, who met his wife Alex while both were stationed in Hawaii. They recently welcomed daughter Scout into the world. Bob, naturally, wants to know the date of the christening.

“Bob’s part of the family,” said Aylward. “He came to my graduation. He goes above and beyond.”

This might also apply to his heritage.

Irish all year long

That’s how U.S. Rep. Richard Neal once described Bob Cahillane, whose countless trips to the Emerald Isle, including many he led, began as a kid. “My mom asks ‘Would you like to go to Ireland with your grandfather?’ I said ‘Hell, when do we leave?’ Over by ship, back by ship two months later, the family farm, no electricity, running water, outhouses, the Puck Fair. Heaven.”

So, back to Hamp in the 50s — all sideburns and juke joints?

He laughs. “As the mayor’s son, the first family of the city, you couldn’t go downtown on a Saturday with dungarees on — you had to be dressed and put together.”

Out of sight, though, he and his sibs were well acquainted with a fast-moving bend of the Mill River. “We had huts and everything, coming home when the streetlights came on.”

When he got home from the service he was called upon to represent the family at a wedding and he ran into a girl he knew from school, Michaela Kiley, known as Mike by exactly everyone. “We had a couple of dances and really hit it off,” he said.

They tied the knot in 1963, bought another former mayor’s house, and raised three boys and two girls.

Politics? Some. He was instrumental in the campaigns of former Northampton Mayor Dave Musante, among others, never afraid to advise the “walking mayor” on myriad matters. “He’d call me up: ‘Cal, let’s take a walk.’ We’d hash it all out.”

Cahillane entered the late Congressman Silvio Conte’s Washington world by telling it like it is. He had arranged for Conte, who he’d never met, to do the dedication at the “Deuce,” the World War II Club, meeting at Bob’s house at 4 p.m. “Typical politician — he didn’t show up. So I went to the club. He arrives at the house, my wife says, ‘You’re late!’ ‘Where’s Bob?’ ‘At the club!’ she says. Oh, he was pissed. But that Navy training kicked right in: you start on time and you finish on time. He did the dedication. The next thing I know I’m playing bocce tournaments with him in Pittsfield and he starts inviting me to Washington. I worked for Sil for 20 years.”

Also on the wall is a picture of the late Matt Graveline, a young quadriplegic with such a joie de vivre, one’s spirit was raised just being around him. Bob brought Graveline breakfast every Sunday for 20 years. “Always upbeat. I’d had another operation and I knew Matt would be worried. I called and they told me he died that night.”

Graveline’s name lives on through a Dollars for Scholars scholarship.

Cahillane’s long career selling cars in the family business with his brothers slowed with the economy, and he soon stepped into a born-to-be role as veterans service officer, a city post he held for 13 years.

Bob’s irrepressible daughter (and former Gazette columnist) Michaela Anne died suddenly in 2018 at the age of 46. “Michaela Anne was brilliant,” said Bob. “She helped set up the euro, working out of London, speaking four or five languages, just amazing. She had a sleep disorder … and she didn’t show up for work and they called me. I found her … my poor wife never recovered.”

Alas, Mike, Bob’s wife of 55 years, died only a few months later.

His health challenges kicked in when he fell in front of the house and annihilated his back. He still has the X-rays, which look like a row of rivets on the shell of a B-29.

With the aid of Guinness, he’ll tell you, he beat bladder cancer and clawed his way back from one crippling calamity to another.

Making the fleet

Retirement, also, didn’t last long. He set his sights on becoming a Blue and Gold Officer, a volunteer, yet vital position with the Naval Academy.

But one higher-up took one look at Cahillane, then 70, his body chewed-up by catastrophe, and told him: “You can’t! It’s a five-year position.” Well, he beat those odds too, and re-upped twice.

“It’s a huge stepping point,” said Cahillane of the USNA. “You graduate, serve your five. All of a sudden you got nine years in, another few years you got your 20.”

“Twenty? We’ll see,” laughed Bob’s most recent grad, Franky Tangredi, 26, of Montgomery. “I’ll put a fair share in, not sure if I’ll get to 20, but I’ve got no complaints.”

The Marine is stationed in Pensacola, Florida, flying helicopters. “I was set on going into aviation,” said Tangredi. “Living near Barnes was a cool thing, the 15s flying over the house.”

He played soccer for Gateway Regional, met Bob by accident through an old coach. “It really was fate, I couldn’t believe it,” said Tangredi. “But he thought I could do it.” He applied to the Naval Academy, as do some 20,000 every year.

“I didn’t get in my first try,” he said. “Bob urged me to do a year in Texas, Greystone Prep. I’m sure he made a couple of pissed off calls, but he set me on my path and lit a fire under me.”

“I’m hoping to make it to the fleet,” said Tangredi, who graduated in 2022 and is almost through flight school. “You start on a Cessna, work your way up to the 73, the Marine training helicopter.” The idea is to master three of these whirring beasts, including the Vietnam-era Huey and the Cobra attack copter.

He and Bob talk every few weeks. “He’s a great mentor. More like a grandfather, actually.”

The grandfather himself may finally be slowing down, but not so you’d notice. “I still feel good,” he said. “A buddy from Hatfield, a eucharistic minister, brings me communion every Friday.”

Though he stopped driving a couple years ago, missing The Big Bad Bollocks’ St. Pat’s show was out of the question, not to mention Dublin’s own High Kings at the Academy of Music. He gets around.

Bob Flaherty, a longtime author, radio personality and former Gazette writer and columnist, writes a monthly column called “Chance Encounters” in which he writes about our neighbors going about their daily lives.