WEBSTER, FREDDIE (8 June 1916-1 April 1947) was an influential jazz trumpeter from Cleveland, Ohio. Although his legacy has been largely forgotten by the general public, jazz historians and fans acknowledge his influence on the American jazz scene. During his lifetime, Webster was an influential jazz artist who worked with other well-known artists of the time period, such as Dizzy Gillespie and Miles Davis. Webster’s impact on the sound of jazz, as well as the meaningful connections he developed with other jazz artists highlights the importance of the Cleveland jazz scene. Webster’s career emphasized the importance of building connections and relationships in developing careers and legacies.

Born in Cleveland to a religious family, Webster grew up singing church songs every morning before breakfast. Webster attended CENTRAL HIGH SCHOOL, where he played in the school band and met TADD DAMERON, another influential jazz artist from Cleveland. After high school, Webster formed his own band, with whom he toured Ohio in 1938 and 1939. By 1939, Webster decided to leave Ohio and his band; he joined Earl “Fatha” Hines’ orchestra thanks to Harry “Pee Wee” Jackson, who was also a Cleveland-born jazz trumpeter. 

In 1941, Webster decided to leave the band and moved to New York City, where he met and connected with great jazz artists like Dizzy Gillespie. He returned to Hines’ group later in the year; the accumulation of jazz talent has been described as “The Incubator of Bop.” Jazz historians, like Joe Mosbrook, call Hines’ group during this time period the birthplace of bebop. Besides Webster, the group consisted of individuals like Dizzy Gillespie, Sarah Vaughan, and Charlie Parker. Although Webster would not reach mainstream popularity in the same way many of his contemporaries would, he still contributed much to the early sounds of bebop and his sound was praised by his colleagues even decades after his passing. Webster’s sound, rather than using high notes and fast passages, utilized his lower register, more measured phrases, and a characteristic “buzzing,” as described by Miles Davis. 

In 1942, Webster played for both the Lucky Millinder big band and Jimmie Lunceford band, where he was reunited with PeeWee. While touring with Lunceford, Webster met Miles Davis in St. Louis. Their friendship would further develop when both were in New York City in 1944; the two would remain close until Webster’s death in 1947. In his autobiography, Davis claimed that he and Webster would go to 52nd Street together, where they would listen to other great jazz musicians. The two would also teach the other. Webster showed Davis how to accomplish his sound while Davis shared techniques and training that he learned at Julliard. The two also bonded beyond music and became personal friends, sharing clothes, money, and advice.

Webster returned to Cleveland in 1946, where he collaborated with Tadd Dameron, his childhood friend, and Sarah Vaughan in the recording of “If You Could See Me Now.” Webster’s recording with Dameron and Vaughan are some of the few recordings left of his playing. Still, accounts of his playing praise his technical skill and tone, and make note of his influence on Dizzy Gillespie, Miles Davis, and the Cleveland jazz scene as a whole.
Unfortunately, Webster’s career came to an abrupt halt on April 1, 1947. Earlier in the year, Webster began touring with jazz saxophonist Sonny Stitt. While in Chicago, Webster was found dead in his room at the Strode Hotel. Although official records state that Webster passed of a heart attack, those close to him dispute his cause of death. In Miles Davis’ autobiography, he claims that Webster was given heroin laced with poison that was intended for Stitt. Regardless of the exact cause of death, Webster passed away at age 30 in Chicago. His burial details are unknown.

Despite his talent on the trumpet, Webster’s primary influence on jazz can be seen in his relationships with other artists. Both Miles Davis and Dizzy Gillespie, well-known jazz trumpeters from the time, were friends with Webster. Davis explicitly claimed that Webster was an influence in his own playing. Tadd Dameron also cited Webster as the reason he pursued jazz as a career. His interactions with other jazz artists, as well as his undeniable talent, cement Webster as an influential jazz artist from the 1940s. Webster’s successful career was not the result of a prodigy but of a talented player who taught, learned from, and worked with others. 

His career is marked with collaboration and friendship; Davis described their relationship through familiar terms, saying multiple times that Webster was “like a brother” and that they shared everything with each other.  Despite his short career and his relative obscurity in the present day, Webster helped shape the American jazz scene. Even without reaching mainstream popularity, the greatest jazz musicians of his time recognized and appreciated Webster’s talent and sound.


Michele Lew

Last updated: 11/29/2022

Mosbrook, Joe. “Chapter 9: Freddie Webster.” In Cleveland Jazz History, Second Edition. 101-104. (Cleveland: MSL Academic Endeavors, 2013).

Miller, Dan. “Freddie Webster: The Best Sound on Trumpet Since Trumpet was Invented.” Dan Miller. https://www.danmillerjazz.com/webster.html

Davis, Miles and Quincy Troupe. Miles: The Autobiography. (New York: Simon and Schuster, 1989).

“Freddie Webster.” WBSS Media. https://wbssmedia.com/artists/detail/1199

“Jazz Remembered: Freddie Webster.” Sandy Brown Jazz. https://www.sandybrownjazz.co.uk/JazzRemembered/FreddieWebster.html 


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