The story of the Pioneer Social Club, better known as just the Pioneer Club, has a “once upon a time” air about it, because the  conditions that allowed it to flourish seem so improbable today.

The Pioneer Social Club occupied a former rooming house on Westfield Street, a side street off Tremont near Camden that ran north for a half-block and ended in an alley. Across the street was a transit authority maintenance yard, and according to the City Directory, the Pioneer was the only address on Westfield. It wasn’t the sort of place you walked past. It had to be your destination.

The Pioneer Club was private, and it charged a membership fee, and as such, it could serve liquor after the regular nightclub closing time. But the Pioneer operated as a bar, selling liquor and not just serving it, and for this, the Pioneer needed friends in the city bureaucracy, and it had them.

The Pioneer Club was owned by brothers Balcom and Silas “Shag” Taylor, owners of the Lincoln Pharmacy, a neighborhood hub on the corner of Tremont and Kendall. The Taylors were old-fashioned ward politicians, delivering Black votes to the Irish Democratic machine in return for political concessions. One such concession was allowing them to operate their private club as a bar after hours without police interference, as long as the club remained quiet and trouble-free.

The Pioneer became a focal point for Boston’s musicians, entertainers, journalists, and other night people. There was always music on the weekends, and sometimes other nights too, if the spirit prevailed. The room upstairs seated perhaps 50, with a small stage and an upright piano, which Duke Ellington once played all night. Jazz was an integral part of the Pioneer, and there were some fine house pianists over the years, like Highland Diggs, George “Fingers” Pearson, and Mabel Simms. The jazz musicians and singers who were in town all stopped by to relax, and sometimes to play. Art Tatum took his turn at that piano, as did Nat Cole, Count Basie, and Miles Davis. A long list of musicians and singers graced that tiny stage.

And so the Pioneer continued on its quiet way through the years. Shag Taylor died in 1958, struck by a car while walking to work, and Lincoln Pope eventually assumed ownership of the club. It was business as usual until early 1973, when officialdom’s tolerance for after-hours clubs dissipated. After Labor Day in 1973, the Pioneer went legitimate, closing at 2 a.m. and ceasing all after-hours operations. It wasn’t the same. In January 1974, the Boston Redevelopment Authority purchased the building and land, and then it was just a matter of time. The club closed in June and the demolition crew started its work on July 18.

The Pioneer was a special place, a congenial place, unique in all of Boston—and most Bostonians had no idea it existed. For those that were aware of it, though, it was the place to be. There hasn’t been anything like it since.

Here is some appropriate wee hours music from Dexter Gordon.