Neighborhood Bookie, Vanishing Breed

One of the few remaining old-school bookies in the town where I grew up just passed away. The computer was not a tool of this gent's trade. He still took bets by phone with pencil and paper from his living room, fighting Internet wagering and fantasy football to the very end by catering to a dozen or so technology-resistant loyalists. Toward the end of his life, “Gus” was missing a leg but not his wise-guy sense of humor, and if you settled up at his “alternate office” in the dim bar of a Veterans of Foreign Wars post, it was like stepping into a Kodachrome time warp that took you straight back to hardscrabble New England in the 1970s.

When I was a kid in a racetrack town, it was customary to tag along with your old man when his errands included a social call to one of the local bookies. This was an implicit lesson to help you figure out how the world worked; today a well-meaning, but misguided state agency might swoop in and seize your kids if they find out you've intentionally exposed them to the evils of betting.

I always thought it was neat how Gus kept a well-stocked Coke machine in his front breezeway. Because my dad and I didn't frequent his house during peak settlement hours, it never dawned on me that the machine's purpose was to offer a quarter's worth of refreshment to the crush of customers who flocked to his house. Decades ago, even low-level bet-takers could count on that steady a volume of local business.

My grounding in the world of gambling was balanced by cautionary tales offset against tantalizing snippets of gray-market escapades. I had one great-uncle who reputedly won–then lost–$1 million dollars booking bets in southern New Hampshire about 10 years before I was born. I only knew him as a soft-spoken older man who was exceedingly generous with the little money he earned in a tailor's shop after his 1957 financial wipeout. By the time I was old enough to be intrigued about his mysterious, unspoken past as a high roller, my great-uncle would only smile wistfully, look away, and change the subject.

At the same time, the other side of my extended family was dotted with great-aunts and matronly cousins who worked part-time as clandestine bet-runners, speeding down back roads with satchels full of cash to lay off sizable wagers at Rockingham Park that the mill-town bookies farther north didn't want to cover. No one would ever have suspected these churchgoing, middle-aged women of illicit activity–which is precisely why they were hired. Rock, like most tracks during that era, made a big show of claiming to want no part of any illegal “comeback money” that might find its way through their mutuel machines. But, of course, management privately realized that the bookies' tainted twenties were the same color as the rest of the bills that flooded the pools, and lady bet-runners from all corners of the region knew to proceed directly to a specific window where expedited service had been pre-arranged between influential parties.

Neighborhood bookies once thrived across America, especially in close-knit New England. Now they're a vanishing breed. Is person-to-person bet-taking a dying form of mildly illicit folklore whose history should be documented? A social scourge whose decline represents a triumph of law enforcement? Or is everyday gambling now so anonymously mainstream that it's gone corporate and bland thanks to technology-driven ubiquity?

This haze of nostalgia isn't meant to gloss over the reality that for some people, illegal gambling has dire social costs. Yet the wiseguys from my youth weren't criminals so much as characters; part of the small-town fabric. Sure, you might read in the papers (or see one of the glut of fictionalized Boston-based movies) about volatile crime bosses higher up the totem pole resorting to mayhem to settle disputes. But the guys your dad dealt with–the neighborhood bookies–remained more or less constant and harmless across generations.

Bookmakers have always been leery of the encroachment of rival bet-takers, but when fierce competition arrived nationwide in the 1990s, it entrenched itself efficiently and without a turf war. The advent of the Internet made many complex forms of betting easily accessible, to the point where today, gambling on horses or sporting events is no longer much of a person-to-
person endeavor.

Old-school bookies either adapt or expire. Some have traded in phone lines and in-person office hours for customized online betting portals (do a Google search for “bookie software” and you'll get 409,000 results). Or-just like in the broader economy-American bookies are even outsourcing their trade overseas, essentially collecting finder's fees for steering customers to offshore bet-processing centers.

It would be an interesting proposition to bet on whether or not in a few decades' time we will recognize some sort of sociological loss tied to the dehumanization of gambling. Do we miss out on something by conducting betting entirely in a cyberspace vacuum? Might the thrills of virtual gambling become diminished or dulled over time when social interaction is increasingly removed from the equation? If we're going to have vices, is one method or the other more aesthetically palatable?

At least one subtlety has been lost: back in the day, if you were a wannabe high roller betting beyond your means, the neighborhood bookie was likely to go directly to your father or uncle in an attempt to straighten you out before you burned though your passbook savings account. Not every spiraling hotshot heeded this advice, but at least they got a chance. Good luck with that happening today if your bet-taker happens to be an anonymous wagering portal based in Antigua.

By age 12, I knew that at funerals among members of our small town's gambling community, the most elaborate flower arrangements were always sent by the neighborhood bookies. I also knew that at Christmas, if you were a longtime customer, betting debts were likely to be forgiven. This holiday courtesy was extended not so much out of seasonal cheer and joy, but because it made good marketing sense–Gus and the other bookies were quite confident they'd rake it all back, and more, once football playoffs started.