“You Know Why”
Harold Leonard And His Red Jackets
(Gennett 5026-A mx 11261) December 11, 1922
“Red Jacket Blues”
Harold Leonard And His Red Jackets
(Gennett 5026-B mx 11259) December 11, 1922
Here is a pre-microphone era record from the Edward Mitchell collection featuring a band with an interesting and rather unique sound. The ensemble consisted of a violin, a sax section, a piano, a banjo, and drums.
“You Know Why” is a charming dance number with an arrangement that comes across well through the primitive recording technology. Indeed, I think the piano solo passage sounds quite nice for a recording of that era, given that it was an instrument that was often difficult to record.
“Red Jacket Blues” is an interesting composition that makes me wish this could have been recorded three years later after microphones began to be used in recording sessions.
The arrangement heavily features Harold Leonard playing the violin and reminds me of something one might hear from some of the later country music bands. Violins did not record well at all with the old technology. Very often, for recording sessions, they would instead use a Stroh violin, a variation of the instrument featuring a horn to amplify the sound. I don’t know whether or not one was used for this recording session.
Harold Leonard’s band is best remembered as the house band of the Hotel Windsor in Montreal in the mid-1920s and the Waldorf-Astoria Hotel from 1926-1927 when it was still at its original location where the Empire State Building would be constructed a few years later. During periods when the band wasn’t associated with the hotels, it went by the name of Harold Leonard and his Red Jackets.
Both of these recordings were made at the Gennett studios in Richmond, Indiana as part of the band’s very first recording session.
Other than his association with the famous hotels, I was not able to quickly find in any single source much information about Harold Leonard or his band.
Based mostly on various publications from the era, prior to its extended engagement at the Hotel Windsor, the band was based in Chicago and was a unit of the Benson Organization, a band booking agency founded by cellist Edgar Benson, that dominated the procurement of live music for that city’s hotels and night spots during the 1920s. The organization’s flagship band is well-known to record collectors and fans of the era’s music as the Benson Orchestra of Chicago, which made many records on Victor.
Famous recording bandleaders whose bands were also units of the Benson Organization included Isham Jones, Charlie Straight, Don Bestor and Jack Chapman.
For hotels and other venues, the agency eliminated the hassle of recruiting and negotiating with individual bands. For bands, the trade-off was between their independence and a steady supply of gigs.
The band’s last records were made during its association with the Waldorf-Astoria. I was not able to find much about what became of Harold Leonard after his band’s engagement at that hotel. The latest mention I found in my limited research was in a June 1929 issue of Variety, which mentioned Leonard had become an orchestra booking executive at the Benson Organization and still had a band, now billed as Harold Leonard and his All Americans, with a current engagement at Chicago’s Palmer House.

From September 1923