Word soon spread around the Street that The Caboose was the hangout for the best and the brightest. You had to have flair to hold your own at the bar rail. The majority of Dennis’ clients were floor brokers, upstairs partners, secretaries, bankers and insurance executives. Last but not least were several lawyers who spent more time in The Caboose than in court. These attorneys, who would bill a client for asking the time of day, gave information free of charge to regulars of The Caboose. The brotherhood of boozers.
The Pope of Pine Street tended his flock with loving care. As busy as the place always was, Dennis knew most everyone and if you came often enough, you enjoyed the privilege of his full range of services: father confessor, judge and jury, psychologist, mediator, job consultant, patient listener, and, most of all, friend, especially to the regulars.
The pinnacle was having a nickname bestowed upon you by Dennis. There was: Fast Freddy, Banker Ben, Lucky Louie, Mr. Money, Bennie Bucks, Stiff Sam, Henpecked Hank, Lovely Louise, Rusty Nails Rita, and. Tiny Tina. There was: Oil Henry (one of the Pope’s proudest nicknames, as he didn’t think many of the regulars got this literary entendre), The Boss (there were a few of those, and Dennis had to be nimble if two came in together), and Mr. Bow Tie (ditto). Also: Slugger, Too Tall, Too Wide, Button Down, Red, Dutch, Shoe Shine, and Tassles.
Regulars ruled the roost, but newcomers were welcome with open arms, especially if they had a good story to tell. Many a conversation at The Caboose began with “Hey, did you hear what happened to…” or “You won’t believe what I saw….” Stories swirled in this collision of booze and bravado, fellowship and oneups-menship.
This was what The Caboose meant to hundreds of men and women: Refuge, release, and a place to swap stories about good or bad luck, good or bad love, sports, money, heroes and villains, and often just too outrageous not to be true. More tomorrow.