Harold Leonard's “Recording” Red Jackets (1922-1926)

Gennett Records, Richmond 11-12 Dec. 1922
1. Red Jacket Blues [0:00]
2. You Know Why [2:33]
3. Fate [5:25]
4. Can You Forget? [8:11]
5. If Winter Comes [11:18]
6. When Eyes Meet Eyes (When Lips Meet Lips) Waltz and Fox Trot [14:04]

Gennett Records, Richmond 12-13 Apr. 1923
7. Some Lonesome Light [17:15]
8. I’ve Got the Ain’t Got Nothing Never Had Nothing Blues [20:13]
9. The Cat’s Whiskers [22:49]
10. China Boy (Go Sleep) [25:01]
11. Tom Tom One-Step [27:49]
12. Some Stuff [30:45]

Okeh Records, New York 3 Jan. 1924
13. Forgetful Blues [33:01]
14. Hymn to the Sun [36:09]

Okeh Records, New York 19 Mar. 1924
15. Limehouse Blues [38:56]
16. Where the Lazy Daisies Grow [41:58]

Okeh Records, New York ca. Apr. 1924
17. Unfortunate Blues [44:46]
18. Goodnight, Sleep Tight [47:31]

*Brunswick Records, New York 18 Jan. 1926
19. Dinah [50:38]
20. (Kentucky’s Way of Sayin’) Good Morning [53:05]

*tracks by Leonard’s Waldorf-Astoria Orchestra.

Transferred with 3.0ML lateral stylus in Audiotechnica VMN70SP cartridge via Audiotechnica AT-LP120 Turntable. Discographic Info and Research from Brian Rust’s The American Dance Band Discography 1917-1942, Newspapers.com, the Billboard, Javier Soria Laso, and Colin Hancock. Recordings from the Colin Hancock Collection.

Perhaps the most famous Chicago bandleader you’ve never heard of, Harold Leonard and his band the Red Jackets were a big deal in their day. The band, their records, and their story offers many opportunities. You get to see a booking agency’s ability to push their bands to higher levels gig by gig. You get to learn of the leader’s own musical story beginning as just young boy. And you get to hear a small society combo turn into a hot orchestra over each enjoyable and experimental recording session. This great band never got its due, so here are 20 early Leonard recordings aiming to help change that.

Harold Finkelstein was born in Chicago on March 16, 1903 to Abe and Sara Finkelstein. At 7 years old, his father purchased him a violin and within five years he was playing professionally. While attending Hyde Park High School, he joined the orchestra and the mandolin club, captained the tennis club, and had steady gigs at the Blackstone Hotel and Willards Cafe. He claimed to have enrolled at the University of Chicago around 1920, but he did not graduate, and may not have spent much time in class.

Around 1921 Finkelstein changed his last name to “Leonard,” and was offered a bandleader position in Colorado Springs. He organized a brassless group called the “Red Jackets,” who were quite well received. Returning to Chicago he began working with the Benson booking agency, playing several significant early 20s Chicago venues including the College Inn, the Aladdin, and the Beachview Gardens, and made their first records for Gennett in late 1922. In April 1923, they started a long gig at the Palais Royale in South Bend, Indiana. Billed as the “Recording Red Jackets,” the band was a smash success and soon made more Gennett Records, adding cornet and trombone in the process.

When this gig ended the band returned to Chicago for a brief stay at the Bismarck Hotel before taking an offer at the Club Madrid in Philadelphia. This was also when the band switched from Gennett to Okeh–Philly’s proximity to New York made it one of Okeh’s go-to’s for soliciting bands including those of Vincent Rizzo, Mickey Guy, and Moe Jaffe.

By the time this engagement ended in June 1924, Leonard’s popularity from the records and radio broadcasts made him a regular daily name in northeastern US newspapers. In fact, it had reached international status–an offer soon arrived from the Windsor Hotel in Montreal, Quebec for the position of orchestra manager. The Red Jackets debuted at the afternoon “dansant” in the hotel’s Grill Room. Their broadcasts over CHYC Northern Electric Radio from 10pm to midnight and sessions for Canadian HMV earned them a large following. The band’s slogan was “There is None Better.”

For the Montreal engagement, the group was billed “WINDSOR HOTEL DANCE ORCHESTRA Harold Leonard’s Red Jackets” in ads, sometimes even putting Leonard’s name in parenthesis. Between this, being in another country, and seeing his career taking off, Leonard may have been ready for a change. Whatever the case, some time around 1925/6 Theodore “Teddy” Mains took over as director of the band, while Leonard took an offer to lead the Waldorf Astoria Orchestra at the hotel of the same name in New York City. This band had a contract with Brunswick Records.

Leonard still managed both groups, even alternating venues for a week in June 1926. The Red Jackets played the Windsor until at least mid 1927, before embarking on several smaller shows around the United States. By 1930, Leonard was back in Chicago leading the Palmer House “All Americans” broadcasting over station WJJD. He continued to have a long career into the 1940s that took him back to Canada and even to Miami. He died in Chicago in 1982.

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