‘Maybe you shouldn’t rob banks’: Judge chastises 61-year-old serial bank robber who robbed his final bank while out on compassionate release for asthma

Clifford Uptegrove, robbing a bank on the left; in a booking photo on the right.

Left: Clifford Uptegrove robbing a bank (U.S. Department of Justice). Right: Uptegrove in a booking photo (Umatilla County Sheriff’s Office).

A Washington State man entering his golden years will also enter the confines of federal prison after admittedly robbing at least 11 banks — the last of which was robbed after he had been granted compassionate release from a prior punishment for the same type of crime.

Clifford Court Uptegrove, 61, pleaded guilty to armed bank robbery in April. On Thursday, he was sentenced to spend the next 280 months behind bars — which equates to 23 years and four months. In sum, the sentence is more or less a compromise between the 25 years requested by federal prosecutors and the 20-year sentence the since-condemned man’s defense attorney asked the court to impose.

The defendant was most recently arrested on Dec. 17, 2021, after robbing a Umpqua Bank branch in Hermiston, Oregon. He pulled out a gun and demanded large bills before making off with $13,690 in cash and then trying to steal a truck, according to a press release issued by the Oregon U.S. Attorney’s Office. Soon thereafter, Uptegrove was spotted by a local police officer, briefly gave chase, eventually gave in, and was arrested without further incident.