Imagine: Duke Ellington and Louis Armstrong, together for one night only, at the Pioneer Club!  One of the better jazz stories handed down in this town involves the meeting of these two giants at the Pioneer Social Club, on Westfield Street. Neither the club nor the street have existed for years, and all involved have passed, so we’ll never know if the story is true. But I choose to believe it.

Ellington: Maybe he played all night

Westfield Street ran one short block north off Tremont Street in the South End, between Camden and Lenox Streets, in a mainly African-American neighborhood. The Pioneer Club was in a nondescript building on Westfield, and it was perhaps the most famous after-hours club in a city that once had many. There was a bar and a kitchen on the first floor, and a room with a small stage and an upright piano upstairs. The club was by no means a secret, but most of Boston was completely unaware of its existence, which was just fine with the ownership.

The Pioneer was a private club, not subject to the regulations governing public nightclubs. And it is where the musicians and entertainers went to relax after their own work was done.

The story is that Louis and Duke played duets until dawn before a delighted audience in that after-hours club. It happened—but when? The only time the schedules work out is February 24, 1960. That night, Ellington played a one-nighter at the Bradford Hotel  ballroom, and George Clarke mentioned in his “Around Boston” column in the Daily Record that Duke invited two guests to sit in with him that night: Louie Bellson and Louis Armstrong. Bellson, his former drummer, was at Blintstrub’s with Pearl Bailey’s show, and Armstrong was scheduled at the Surf in Nantasket two days later. Duke was scheduled for Worcester on the 25th, so neither had pressing travel plans.

So there were two musical giants at loose ends in early-to-bed Boston.  Where else could they go to relax but the Pioneer Club? Given their relentless touring, few after-hours opportunities like this came their way. Globe reporter Bill Buchanan remembered them  “upstairs in the function room with Duke sitting at the battered piano and Louis, handkerchief in hand, singing away. And it all ended at 6 a.m.”

Of course there is no conclusive proof that this event took place overnight on Feb 24-25. But I’ve examined itineraries and whole volumes of Boston newspapers, and chatted with a witness, and this, I am convinced, is the day. So here’s a tune for the lucky so-and-sos who were there that night over fifty years ago.