Pianist Leo Montgomery is a lively player who spent decades on the Chicago jazz scene with apparently not much to show for it in terms of recorded documentation. Considering that few listeners may come across this pianist in the first place, perhaps it is unnecessary to point out that it is a rare jazzman with the surname Montgomery who is not part of the same family from whence sprang Wes Montgomery, Buddy Montgomery, and Monk Montgomery. When including the pianist in his Who's Who in Jazz, author John Chilton also saw fit to point out that Leo Montgomery is not related to bluesman Eurreal "Little Brother" Montgomery.
Like many jazz artists, the unrelated Montgomery had a strong interest in dance. One main reason for his lack of involvement in the recording industry may have been this interest basically overwhelming his jazz activities following the Second World War. While hostilities were still raging, Montgomery had begun setting up his own dance studios in the Windy City. Out of this evolved a series of dance revues and floorshows which in some cases removed Montgomery from the piano bench entirely; instead he may have been occupied observing the moves of his troupe from the sidelines.
He did not give up piano completely and was known to take gigs when he was approaching the age of 70. Perhaps he lost interest in performing jazz more regularly due to the difficulties of working in the genre. It would certainly seem frustrating if, as appears to have been the case, some of the most talented players in jazz created the greatest hurdles for their working associates. It is hard to think of a set of musicians as magnificent as clarinetist Johnny Dodds and his little brother, drummer Baby Dodds, yet newspaper accounts from the '40s illustrate the sort of difficulties faced by their loyal pianist. "Johnny Dodds had to have all his teeth pulled," begins one epistle, "leaving Natty Dominique, Baby Dodds and Leo Montgomery to do all the work at the 9750 Club." On another night in the harsh winter of 1940: "Johnny Dodds is playing clarinet again. Partly recovered from his recent serious illness, and reinstated in the musicians' union which recently expelled him for non-payment of dues...." And so forth.
Montgomery's exposure to such travails could have begun when he was even younger, although maybe not as a child. His parents' strong interest in music never led to professional activity for either of them. Bandleader Hayes Alvis elevated the family into the professional category by taking an interest in the pianist son, an association that, like much of Montgomery's career, comes complete with a Chicago neighborhood vibe, in this case Melrose Park circa the Roaring Twenties. The Dodds connection followed in the '30s, as did gigs with two violinists, Carroll Dickerson and Erskine Tate. Employment in the latter outfit stretched over a period of several years. Other working relationships for the pianist included Gerald Casey & His Musical Ambassadors in the early part of the decade and the Freddie Williams band.