In November 1934, he was arrested in Raleigh, North Carolina for auto theft and served 18 months, first in Ohio and then at a prison camp in Petersburg, Virginia.

In July 1936, he was arrested for possessing burglary tools but escaped from the Miami county jail before being recaptured and serving time in Raiford.

After being released from prison in May 1973, he joined the payroll of Chicago Teamsters Local 714 while moonlighting as a burglar in Youngstown, Ohio.

[5] At the time, Montos had been a fugitive for nine years, having been convicted in absentia for robbing an Indiana jewelry store.

[2] Montos was sentenced to serving 33 to 40 years for the Brookline robbery and sent to the Massachusetts Correctional Institution — Norfolk.

[citation needed] Several prisoners started a petition along with Massachusetts residents so he could live his last days with his elderly sister in Florida.