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.

Historical photo


1859-1859 Wm. Van Olinda
1859-1862 David M. Mills
1862-1864 Henry Schneider
1865-1866 Philip Smith
1867-1867 George Goodnow
1868-1868 Phlip Smith
1869-1869 Joshua P. Riley
1870-1870 Thomas McElhenny
1871-1872 E. E. Van Sickle

1872-1872 Henry Crofut
1873-1876 John L Innis
1877-1880 James Hopkins
1881-1881 S. R. Jackson
1882-1886 Gustave Haerling
1887-1887 F. D. Fuller
1888-1895 Wm. Boyle
1896-1896 W. E. Herron
1897-1903 O. F. Herron

1903-1912 Peter Arendt
1913-1929 Hugh Maxwell
1930-1935 R. E. Rippey
1936-1964 Frank Scholer
1965-1968 James Mertes
1969-1978 Ed Guntren
1979-1990 Dave Stock
1990-2020 Mike Van Otterloo
2021-Jeff TeBrink