Of Sam’s birth and formative years, very little is surely known. According to legend, Suitcase Sam was born Leon Stanislaus Czologosz on 8 September 1988. It is believed that he is the great great grandson of the anarchist Leon Czologosz, who, on the sixth of September 1901, shot and killed President William McKinley in Buffalo, New York. The circumstances and lineage of his mother remain shrouded in mystery.

Sam's father, Alexander Berkman Czologosz, was a railroad engineer with the Central Pacific, operating out of Newcastle, California. From 1985 to 1998, Sam lapped up the miles, and licked the valleys up—he peered into shanties by the sides of the roads and there seemed to stand before the world as it has always been.

It is believed that it was there on the train line that Sam drank up the great American musical traditions—his grizzled protectors on the engine yard filling him brim-full with religious awe, laying him reverently down at the feet of the old masters: Mississippi John Hurt, Emmett Miller and the great Jimmie Rodgers. Young Sam distinguished himself, though still a child, by his unique guitar and vocal stylings, and by a genteel demeanor that seemed beyond his years. Loved though he was on the Central Pacific, when he was just fourteen he struck out on his own.

His professional career began with the Hell-Bound Fiddle Band, working out of a bar room near Pontoon Crossing on the Pecos River. There he studied the great traditions of American fiddle, Cowboy poetry, Swiss yodeling, and the Hokum blues. He became a connoisseur of ragtime string, the Lomax collection and the very best of Memphis jug; he drank from the fountainhead of the muses: the Mississippi Sheiks, the Ascension Choir, Sonny Boy Terry and Brownie McGhee.

In 2010, Sam moved north, to Toronto, Ontario and released his first record under his own name: Get It To Go on PLEASENCE Records.  The sound of the Get It To Go EP was inspired by 1920's traditional Jazz and drew comparisons to Leon Redbone and Mose Scarlett. The release was followed by a short tour of Canada in support of the record. 

In 2012, the song The Sweetest Hippopotamus, from the Get It To Go EP, was adapted into the BravoFACT short-film by the same name. Suitcase Sam, who appeared as himself, composed the music for the film and went on to win the Best Soundtrack Short award at the AOF International Film Festival. 

In late 2014, Suitcase Sam released his second EP: Waiting on a Train; a small collection of songs inspired by 1930's country music, particularly the music of Jimmie Rodgers. The Following eighteen months were spent performing live concerts in support of the EP. During this time, Sam opened up for Courtney Barnett, Benjamin Booker, Bloodshot BIll, John Cragie, Mikal Cronin, CATL and Elliot Brood. This period culminated with a short tour of New York City in late 2016. 

Suitcase Sam joined Curve Music in 2019 with the release of (a repackaged) Get It To Go EP which includes bonus tracks from the award-winning soundtrack for The Sweetest Hippopotamus.  At the end of 2019, Suitcase released his first LP: Goodnight Riverdale Park on Curve Music.