History

In 1858, Plymouth County was separated from Woodbury County and the Woodbury County Court appointed William Van Olinda as the organizing Sheriff of Plymouth County. Van Olinda took the post of County Judge, and made appointments to other offices, and named David M. Mills as the Sheriff of Plymouth County. Mills served from 1859-1862.

Many early sheriff's had short terms, however Sheriff Hugh Maxwell (1913-1929) served through most of the "Prohibition Period". Plymouth County was strategic for "booze-runners" trying to get their contraband out of the state or into Sioux City. Also a large number of stills were at work inside the county, these were often moveable and on short notice, hard to find. Confiscated liquor was often turned over to the local hospital for medicinal purposes.

In 1919, four bank robbers broke out of jail when Mrs. Maxwell came to serve them dinner. The sheriff's wife was knocked out and the robbers used a gun to shoot and wound Sheriff Maxwell and kill his son. It was suspected that the gun had been smuggled into jail earlier in a cake. The escapees were captured about two days later in South Dakota.

In 1933 Sheriff Ralph Rippey (1930-1935) dealt with the Farm Holiday Movement and some violence that came with it. Protesters blocked roads to stop the shipment of produce. The sheriff came under criticism when protesters against farm foreclosures attacked Judge Charles Bradley. They dragged him out the courthouse and threatened to hang him, unless he promised not to sign foreclosure notices. The judge refused to give in and was roughed up and left on the east county road to find his own way back to town. Sheriff Rippey was said to have fallen asleep in the jailhouse while this was going on.

Sheriff Mike Van Otterloo (1990-2020) was the longest running sheriff to date.