Darby O’Brien

Owner, Darby O’Brien Advertising

This Unconventional ‘Mad Man’ Has Always Been Ready for a Fight

Photo by Bob Zemba, Simple Truth Imaging

They call it the Fishing Buddies Lodge.

It’s a very informal meeting space within the suite of offices for Darby O’Brien Advertising in South Hadley, and, obviously, it is decorated to look like a fishing cabin.

It is crammed, as in crammed, with collectibles and wall art that start to tell the story of the founder of this company. There are bobbleheads, baseball gloves, New York Yankees and Mickey Mantle merch (he’s a long-time fan of the team and grew up, as many his age did, idolizing #7), a scale model of the Bluesmobile, various photos of JFK, countless mugs, hats, and, on the wall, a framed, autographed photo of Ken Osmond, famous for playing the insincere flatterer and provocateur Eddie Haskell on the classic sitcom Leave It to Beaver.

“I was a fan of Eddie’s — he was the king of mischief,” said O’Brien, the Holyoke native who shares that trait with Haskell, one of many that make him a unique character, in every sense, and contribute to his being named a Difference Maker.

Others include creativity — his ads certainly stand out as different and, generally speaking, effective — as well as genuineness, sincerity, and a passion for getting involved, often with underdog groups and causes.

“On the way out, Jeremy grabbed me by the arm and said, ‘will you fight for us? Because we can’t fight.’ I said, ‘yeah, I’ll fight to the finish, because this is wrong.’”

With that last one, there is a long list, everything from efforts to reopen Holyoke’s reservoirs to fishing and bring back his childhood baseball team, the Elmwood Jets, to lobbying against the quarrying of a local ski area with his ‘Mount Tom, I Don’t Dig It’ campaign; from early efforts to thwart casino gambling in Springfield to a campaign protesting the Western Massachusetts Economic Development Council’s (EDC) decision to hire a Tennessee-based firm to rebrand the region for tourism efforts, rather than use local marketing talent.

And then, there was the Phoebe Prince case.

Prince was a student at South Hadley High School when she took her own life after persistent bullying. O’Brien is credited by many with taking the case to a regional, national, and even international stage, attention that eventually led to charges against several students and the passing of anti-bullying legislation at the state level called ‘Phoebe’s Law.’

Soon after the matter starting getting press, O’Brien remembers getting a call from Prince’s parents, Jeremy and Anne, asking if they could meet with him.

“On the way out, Jeremy grabbed me by the arm and said, ‘will you fight for us? Because we can’t fight,’” he recalled. “I said, ‘yeah, I’ll fight to the finish, because this is wrong.’

“No one was standing up,” he went on, adding that he pressed the matter, despite repeated warnings that it would be bad for his business and, eventually, several death threats.

But as with other cases in which he’s gotten involved, he’s ignored such warnings and plowed ahead. Indeed, while he likes to say he’s gotten involved in most of the issues listed above “by accident,” those who know him well say otherwise.

“He literally does not back down from a fight or a wrong,” said John Garvey, a friend and fellow marketing firm owner. “And he encourages other people to not back down when they see a wrong.”

This is certainly the case with a weekly blog of sorts that he started at the height of the pandemic as a way to keep people connected, informed, and even entertained, and also to generate dialogue on the issues of the day.

While some offerings are whimsical, such as taste testings (fruitcake and Twinkies, for example) involving his grandson, Flynn, others are poignant and thought-provoking, such as a recent tribute to his brother David (known to most as ‘Moon’) who died last month, a remembrance of one of the students shot at Kent State in May 1970, who died recently, and sharp criticism of Newton officials for making a man take down an ice rink he created in his front yard during COVID because he lacked a special permit.

“Imagine doing that to kids during this COVID-19 winter?” O’Brien asked rhetorically. “Jackasses. Look the other way and let the kids have good, clean fun, will ya?”

Such sentiments, and the williness to express them, help explain why he’s a true Difference Maker.

Getting the Message

O’Brien said he took note of all the things marketing experts said not to do as he was starting his business — such as not getting involved with retail or political campaigns — but, by and large, he ignored them.

Indeed, among his first clients were the men’s clothing store A.O. White and Holyoke mayoral hopeful Marty Dunn, who was waging an underdog (there’s that word again) campaign to unseat long-time incumbent Ernie Proulx.

“He was a sure-shot loser because Ernie Proulx had been mayor for 12 years, he won every ward, every precinct, and had a reputation for demolishing Irish candidates,” O’Brien recalled, adding that he drew inspiration from boxer Sugar Ray Leonard’s ‘stick-and-move’ tactics to defeat Marvin Hagler and ran a successful campaign that he called “a real strong statement about being creative.”

Suffice it to say that O’Brien has been doing things his way — not the way the experts advise — since he started his company — and, actually, long before that.

Like when he was in high school — actually, several of them, as it took him six years and several institutions to earn a diploma. He said he joked to his frustrated father, a vice president with the construction firm Daniel O’Connell’s Sons, “dad, the longer I’m in school, the smarter I get.”

He added that “I hadn’t really thought about advertising, although I was kind of a promoter as a kid.” But he was eventually “discovered” by the owner of the local firm Bewick Advertising.

“He called me, hired me, and put me in charge of new business, which I knew nothing about,” O’Brien recalled, noting that he eventually started his own agency in 1980, taking with him many of his clients from Bewick and focusing on the goal of getting more of the larger businesses in the region to use local marketing talent.

Over the course of roughly 45 years in business, O’Brien has made his mark in many different ways, starting with his approach to marketing — which is to almost dare clients, and potential clients, to look beyond what would be considered safe — something he laments that very few are willing to do now.

His ads can certainly be defined as different and creative, to the extent that the phrase ‘Darby ad’ has entered the lexicon, a reference to something bold — and at times controversial — that stands out.

One of the many marketing initiatives that could be described with the phrase ‘Darby ad.’

Like the billboard featuring a Hot Table panini and the headline ‘Bite Me.’ Or the billboard for lawyer Raipher Pellegrino with the words, ‘The Iceman Sueth.’ Decades ago, there was a newspaper ad for the Springfield Civic Center promoting a tennis match at the then-Springfield Civic Center between Springfield native Tim Mayotte and Czechoslovakian Ivan Lendl. The headline read, ‘On February 9, BayBank Invites Tim Mayotte Back to Springfield to Bounce a Czech.’

As O’Brien tells the story, Lendl called the event organizers saying that was backing out of the match due to the ad, which he considered offensive, then started laughing, saying he was just kidding.

Then there’s the ad O’Brien put together for a group opposing casino gambling in Springfield. Featuring a picture of a masked man pointing a gun at the reader, it took the headline, ‘If You Build It, They Will Come.’

“You hire Darby because you want ideas,” Garvey said. “You don’t hire Darby to run your ideas by him. And for God’s sake, don’t fight him on the creative — because that is holy ground.”

Peter Rosskothen, the serial entrepreneur who has been a client of O’Brien’s for more than 30 years and worked with him on campaigns for the Log Cabin Banquet & Meeting House, the Delaney House restaurant, and his current venture, Delaney’s Market, agreed — sort of.

In fact, he has fought him on creative content on a few occasions, but most of the time, he’s been talked into ads that were, well … different.

“He likes to push the envelope, and he makes a difference with his uniqueness,” Rothkossen said. “He’s very bold, and he tells me as a client that I’m being too conservative. I like that — I like the fact that the material tends to be different and stands out.”

Taking a Stance

While his marketing and advertising impact has been noteworthy, so too has O’Brien’s work within the community, much of which has involved young people, Holyoke, or some combination of the two.

Such as his efforts to reopen the Paper City’s reservoirs to fishing, a campaign that featured a group he created called the Fishing Buddies, and some escapades involving O’Brien and Peter Jourdain in Blues Brothers-like outfits. He said this effort started by accident when he and an acquantaince, who fished the reservoirs when they were young, tried to relive old memories several decades later and were chased off by police.

The Fishing Buddies Lodge at Darby O’Brien Advertising is crammed with collectibles that speak to O’Brien’s interests — and passions.
Photo by Bob Zemba, Simple Truth Imaging

“There’s no reason why inner-city kids can’t fish out here,” he said, adding that, while the fight was ultimately unsuccessful, despite widespread support — the reservoirs remain closed to fishing — he had some fun and gave people something to think about. And that could be described as his MO.

It was the same with the EDC’s decision to hire a Tennessee firm to rebrand the region. After the ad campaign was created, O’Brien famously challenged then-EDC President Allan Blair to a winner-take-all ping-pong game in an ad that appeared in BusinessWest.

“I told him that if he beat me, I’d shut up and he could put me on his board, and that if I beat him, he’d give the work to the local talent,” said O’Brien, adding that, while Blair never responded, he got his point across, and had some more fun.

With the Phoebe Prince case, though, his involvement was taken to new and far more serious levels.

Encouraged by his father, who thought South Hadley officials were trying to sweep the matter under the rug, O’Brien reached out to Boston Globe columnist Kevin Cullen and went on the record for a piece titled “The Untouchable Mean Girls,” which was essentially the first news story to suggest that bullying was the root cause of Prince’s suicide.

“All hell broke loose,” recalled O’Brien, adding that national and global media were soon all over the story. Soon thereafter, he met with Prince’s parents and committed to do whatever he could to generate more press and hold those responsible accountable. And in the months and even years to follow, he was the subject of threats to his business, health, and life.

Rosskothen said he’s one of many who have, over the years, advised O’Brien that it might not be good for his business to get involved — with the Prince case, but also many of the other issues he’s become entangled with.

“A conversation like that with Darby is a pretty normal conversation because he pushes hard,” Rosskothen said. “As a friend, I sometimes tell him that; he listens, but that doesn’t mean that he follows the advice.”

O’Brien continues to push for what he considers right in his weekly blog, which he calls “Keep Up Your Dukes,” something he said repeatedly to a close friend during his recent cancer fight.

He acknowledged that the more common phrase is ‘put up your dukes,’ a nod to someone that you’re ready to fight and that they should bring it on. His take is different — meant to say that one should always be ready to fight when necessary.

He’s always been that way, and that’s what makes him a Difference Maker.