On the first trip for the Boston Latin Bogeymen, the star attraction was North Berwick's famed West Course, heralded by all who have played it. From left: Jim Carris, Mike DiCarlo, Dan McCarthy, Chuck Longfield, Steve Mahoney, Pat Daly, Tom Flaherty, and Jack Doyle.
Oct 29, 2025

Tapping into the deepest of roots, a special group enjoys golf and friends

To study the majesty, the pride, and the fortitude of the tallest and sturdiest of trees is to understand the might and aura of deep roots.

To hear the story of a group of men and how an annual pilgrimage continues to strengthen friendships of nearly 60 years is to offer reverence to two components that have the sturdiest of roots. Golf and Boston Latin High School.

For your consideration:

Documented reports tie golf’s history to 1456 when the game was first played – in Scotland, of course. And public education in America? You look to where it all started, the Boston Latin School, born in 1635, a year before the country’s first college, Harvard, arrived on the landscape.

So we’re talking serious roots here.

But where are we headed with a story that connects golf and an esteemed breeding ground of premier learning such as the Boston Latin School? Glad you asked, because there’s a group of eight BLS graduates whose stories of camaraderie, loyalty, career success, and philanthropy are inspiring on one hand and downright joyous on the other.

That they call themselves the BLS Bogeymen and have been globe-trotting for 14 years with an annual golf trip to satisfy their passion for the game and salute friendships that are in their seventh decade makes you look for a starting point.

Which lands us at Mike DiCarlo, who is nicknamed “the Commodore” by his fellow Bogeymen – and mind you we are not dealing with marinas or yachts.

“But Mike is the leader of our fleet. ‘Primus inter pares,’ “ said Steve Mahoney, showing that he hasn’t lost any of his Boston Latin skills, even though he and his fellow Bogeymen became seventh-grade classmates in the late 1960s and graduated in high school in 1973 and ’74. “He organizes great golf trips. He’s our leader. He’s first among equals (which is the translation of Primus inter pares).”

Thanks to one of the many fascinating chapters of his life, DiCarlo first came to my attention and prompted a story on the sports pages of the Boston Globe 20 years ago. The gist of the tale was his love of golf, his penchant for the Auld Grey Toon (St. Andrews) and a particular building that sat across the street from the first tee and 18th green of the Old Course.

Michael’s vision and unwavering respect for golf took that story on a trajectory it might never have had, and while his role was only at the beginning of what is now Hamilton Grand – a luxury apartment building – still serves as a reminder of the connections this Hyde Park native has in golf.

Now put aside the urge to revive talk of Hamilton Grand and how it eventually fell into the ownership of the late Herb Kohler’s golf empire; Mike DiCarlo’s life has moved forward quite beautifully and we offer another story that revolves around St. Andrews to introduce this tale of the Bogeymen.

It was about 15 years ago when DiCarlo told a group of seven fellow Boston Latin graduates that he was selling his guest home in St. Andrews, the Monarch House, and that they just had to join him for one last hurrah there..

Thus was a society of sorts born.

“Golf is the conduit for our story,” said DiCarlo. “We genuinely like each other. We care about one another; we care about our wives and our families.

“When I look at this group of friends, I realize that something magical happened with us at Boston Latin (most of them met as 7th graders in 1968).”

What he sees is “a group of city kids who, by dint of hard work and a few breaks, turned out all right.”

Boston Latin High School, whose heralded alumni across five-plus centuries includes five signers of the Declaration of Independence (John Hancock and Benjamin Franklin among them), needs no introduction, but these members of the Bogeymen, deserve one.

The common denominator is their upbringing in the Boston neighborhoods, none of them products of wealthy families, all of them blessed that a quest for academics that was drilled into them by parents of meager means.

“The neighborhoods helped define who you were,” said Dan McCarthy, president of the Class of ‘74. “We all got lucky but we’ve never forgotten where we came from.”

So with great pride they will tell you how their years at Boston Latin molded them. The rollcall – DiCarlo from Hyde Park; McCarthy from Jamaica Plain; Mahoney, Mark Kelly and Paul Heanue from Roslindale; Tom Flaherty from South Boston; Phil Devlin from West Roxbury; and Chuck Longfield from East Boston – is of boys who applied their scholastic aptitude to get into BL, then pushed it to the max to stay in; who followed strict class rules and even stricter parental guidance; who played sports at the playgrounds without any organized supervision; who discovered early on at BL that the golden rule was simple – learn to get along.

Post high school, these men matriculated at premier colleges (Harvard and Northeastern, Boston University and Middlebury, UMass and the Air Force Academy), went on to get MBAs and graduate school honors, and earned professional stature working in banking, wealth management, financial services, health data analysis, engineering, aviation, and science.

There is immense pride in the journey they have made but never is the starting line forgotten.

It is a trip that golf purists crave, a journey to the land of Donald Ross and Royal Dornoch. From left, Mike DiCarlo, Dan McCarthy, Phil Devlin, Paul Heanue, Tom Flaherty, Steve Mahoney, Mark Kelly, and Chuck Longfield.

“I remember the first day when we were told to look to our right, then to our left,” said Flaherty. “We were told one of us wouldn’t be there (as graduates). But here we are nearly 60 years later.”

Graduates, for sure. Friends, most definitely. And if there ever was a motto that they all embraced, it was this, said McCarthy: “Work plus desire equals success.”

Their first trip to St. Andrews was such a rousing success, DiCarlo said he annually gets the same answer to his proposal for next year: “Mike, put together the trip. I’ll be there.”

There have been several trips to Scotland, a couple to Portugal, and they have also gone to Italy and Spain. The laughs have been generated in a handful of languages and accents that are thick and flavorful.

At North Berwick in Scotland, Flaherty’s errant shot brought a scowl to his caddie’s face. “Tom, you are perfectly (obscenity deleted) here,” said the caddie, who was aghast when Flaherty somehow pulled it off. “Tom, your game is caviar or cabbage,” said the looper.

On their trip to the Scottish Highlands, the Bogeymen played at Brora Golf Club. “We were amazed to see fences around the greens to keep the sheep out,” said McCarthy, “and we’d take shots with the cows just 20 feet away.”

Another day at North Berwick, DiCarlo was so wide left with his shot that he told his caddie to give him an 8-iron and he headed to the beach. “Are you out of your mind?” his caddie exclaimed. But somehow DiCarlo pulled it off and the story lives in perpetuity in that Scottish town.

“Sometimes the golf isn’t so great,” laughed Flaherty. “But we always pick each other up. We rag on one another. We applaud one another.”

They wholeheartedly deserve the applause, because in a world where loyalty and commitment are sadly becoming obsolete, the Bogeymen are saturated in these vintage qualities.

With profound reverence for the educational opportunity given him, Mahoney speaks for the group when he says, “Boston Latin changed the trajectory of my life.”

And when you sprinkle in the magic of golf, that game that is a lifetime endeavor and an unmatched elixir, Mahoney said the golf trips DiCarlo arranges ignite emotions he felt long ago.

“I feel like I’m on a team again,” he said. “When I go on these golf trips, I get the same feeling that I got when got on the team bus for (football) games at Latin and Middlebury.”

Give credit to the deepest of roots.