History of the Monroe County Sheriff's Office



The Office of Sheriff is one of the oldest offices known to the common law system. Historians generally agree the origin of the first sheriff’s office was 1,000 years ago, during the Norman Conquest of England. Some date it back even farther and profess that the origins of the office of Sheriff actually stems from the Roman Council and the Earl or Count of that council was the prototype for the modern-day sheriff.

Historians do, however, agree the origin of the word “sheriff” evolved from two Saxon words: “Scyre”, the Saxon word for county and the word “Reve” the Saxon word for keeper. The pronunciation of the two words evolved into the modern word “sheriff”, signifying county-keeper.

The Monroe County Sheriff's Office was established in 1823 as the primary law enforcement agency in the Florida Keys.

Past Monroe County Sheriff's Include:

C.F. Dupont

C.F. Dupont
1889 - 1893

Francis Knight

Francis Knight
1893 - 1901
1905 - 1909

Richard Hicks

Richard Hicks
1901 - 1905

Clements Jaycocks

Clements Jaycocks
1909 - 1917

Cleveland Niles

Cleveland Niles
1926 - 1933

Karl Thompson

Karl Thompson
1933 - 1941

Berlin Sawyer

Berlin Sawyer
1941 - 1953

Jack Spottswood

Jack Spottswood
1953 - 1963

Henry Haskins

Henry Haskins
1963 - 1965

Reace Thompson

Reace Thompson
1965 - 1969

Bobby Brown

Bobby Brown
1969 - 1977

Billy Freeman

William Freeman
1977 - 1989

J. Allison DeFoor

J. Allison DeFoor
1989 - 1990

Richard Roth

Richard Roth
1990 - 2009

Bob Peryam

Robert Peryam
2009 - 2013

Rick Ramsay

Rick Ramsay
2013 - Present

There have been 35 Sheriff’s of Monroe County since it was incorporated in 1823 including:

  • Lemuel Otis, 1829
  • P.B. Prior, 1830
  • Robert R. Fletcher 1832-1840
  • Benjamin A. Vun, 1841
  • Samuel T. Vail, 1842
  • B.K. Kerr, 1842 - 1844
  • Edwin Page, 1844
  • John Coslin 1845-1847
  • John V. Ogden 1847-1849
  • Robert Clark 1849-1858
  • Edgar A. Coste 1858-1861
  • D. B. Cappleman, 1861 - 1864
  • Francis Gunn 1865-1867
  • James G. Jones 1868 - 1874
  • James Roberts 1875-1877
  • Richard Curry 1877-1879
  • George A. Demerrit 1881-1888
  • Charles F. Dupont 1889-1893
  • Francis..W. Knight 1893-1901
  • Richard F. Hicks 1901-1905
  • Francis W. Wright 1905 - 1909
  • Clement Jaycocks 1909-1917
  • Angus H. McInnis 1917-1921
  • Roland Curry 1921-1926
  • Cleveland Niles 1926-1933
  • Karl O. Thompson 1933-1941
  • Berlin A. Sawyer 1941-1953
  • John Spottswood 1953-1963
  • Henry Haskins 1963-1965
  • Reace Thompson 1965-1969
  • Robert L. "Bobby" Brown 1969-1977
  • William "Billy" Freeman Jr. 1977-1988
  • J. Allison DeFoor 1989-1990
  • Richard D. Roth 1990-2009
  • Robert P. Peryam 2009 - 2013
  • Rick Ramsay 2013-Present

Significant Events

Some significant events which have occurred in the history of the Sheriff’s Office include:
  • 1823 - Monroe County was established, along with the office of Monroe County Sheriff.
  • 1828 - City of Key West was incorporated with a population of 300.
  • 1835 - The construction of the first Monroe County Jail was completed and turned over the Sheriff Robert Fletcher in May, 1835. This jail stood on Thomas Street between Southard and Fleming Streets until the early 1870’ it was torn down.
  • 1845 - The second jail was built on the location of the current Courthouse Annex while John Costin was sheriff. There was a possible renovation that occurred in 1880 and the original jail was closed in 1965. The Courthouse Annex and a new jail were built around the original jail in 1965. Renovations have since taken place in 1980 and 1985. Portions of the original jail are still in existence.
  • 1880 - Remodelig of the old jail.
  • 1901 - Deputy Frank Adams was the first deputy killed in the line of duty. Deputy Adams was shot and killed October 7, 1901, while attempting to arrest a man who had interfered with him in the discharge of his duty. (Click here to go to the page for fallen deputies and more detail.)
  • 1905 - Deputy Guy M. Bradley was the second deputy killed in the line of duty. Deputy Bradley, a game warden hired by the Audubon Society and deputized by Sheriff Richard T. Hicks, was shot and killed July 8, 1905, while attempting to arrest a man for killing egrets in the Everglades. (Click here to go to the page for fallen deputies and more detail.)
  • 1935 - September 4, 1935. Sheriff Karl Thompson reported to the Board of County Commissioners that the deposit for the month of August in the First National Bank equaled $102.66 in the collection of fees.
  • 1959 - The Plantation Key Substation was completed at 88700 Overseas Highway while John Spottswood was sheriff. Today, that substation has been named in his honor.
  • 1962 - The Marathon Substation was completed at 3103 Overseas Highway while John Spottswood was sheriff.
  • 1965 - The Monroe County Sheriff’s Office dealt with the aftermath of Hurricane Betsy which came ashore in the Middle Keys.
  • 1969 - Sheriff Brown submits a budget of $848,291.00 to the Board of County Commissioners.
  • 1970’s - During the 1970’s, drug smuggling became almost epidemic in the Keys. Records indicate the Sheriff’s Office seized 207,019 pounds of narcotics from 1975-1977 alone; with a value of approximately $82,807,600.
  • 1973 - The Sheriff’s budget was $1,308,560.00. The Sheriff’s Office was employed 88 people.
  • 1975 - Sheriff’s budget submission of $1,888,370.00 was rejected on July 30th as the Board of County Commissioners exercised their rights under Florida Statute 30.49(4) and modified the budget to $1,736,211. Sheriff Brown was asking for seven additional employees and appealed the budget all the way to the Florida Cabinet. The Cabinet voted 5-2 to raise Brown’s budget as requested but the decision was vetoed by Governor Reubin Askew.
  • 1976 - Sheriff’s budget submission was $1,996,371. This increase from the previous year’s budget was due to Sheriff Brown asking for a 10% cost of living raise for his present personnel, seven new positions of which four are patrolmen and three are detectives and a contingency fund increase of $63,000 for the cost to consolidate City of Key West Police and Sheriff’s Office communications which had been recently approved by a federal and state grant.
  • 1977 – Sheriff Freeman’s budget submission was $3,108,516.00. A large portion of the increase stemmed from Sheriff Freeman’s increase of 40 new employees, the abolishment of the municipal courts and the large number of narcotics arrests, which caused the jail population to jump from an average of 45 to an average of 100 prisoners per day. The Sheriff’s Office employed 114 members.
  • 1978 - Sheriff William Freeman submitted a budget of $2,441,684.00. A $666,832.00 decrease from the year before. The Sheriff’s Office employed 121 members. Sheriff William Freeman purchased ten new patrol cars using confiscated drug smuggling vehicles and boats as trade-ins. On December 10, 1978, jail inmates went on a hunger strike, but called it off just before lunch.
  • 1979 - Sheriff William Freeman submitted a budget of $4,468,028.00. The Sheriff’s Office employed a total of 157 members.
  • 1980 - The Mariel Boat lift brought more than 125,000 refugees to the United States, most of them through Key West. Sheriff William Freeman submitted a budget of $4,045,758.00. The County Commission granted him $3,566,685.00. This $3.5 million fell short of actual expenses and Sheriff Freeman requested and additional $324,088.00 from Commissioners on April 21, 1981. The Sheriff’s Office employed 161 members.
  • 1981 - Sheriff Freeman submitted a budget of $9,586,390.00 - a 134% increase over 1980’s estimated expenditures. The Board of County Commissioners approved a total budget for 1981 of $4,231,354, an increase of $135,907.00 or 3.3% over 1980’s estimated expenditures. The Sheriff submitted his appeal on July 20, 1981 in response to the Commission’s actions and the Commission then added another $1,672,431.00 to the Sheriff’s budget bringing it to $5,903,785.00. Freeman would not accept this figure and proceeded with his appeal to Tallahassee. The Commission then reduced the budget to the original level of $4,231,354.00. The Office of Planning and Budgeting in Tallahassee assessed the situation and made a recommendation of $5,748,669.00, an increase of $1,653,222.00 or 40.4% over 1980’s estimated expenditures and an increase of $1,517,315.00 or 35.9% over the amount approved by the County Commission.
  • 1987 - Sheriff’s Office headquarters moved from the Courthouse Annex building into the new Lester Building located at 530 Whitehead Street while Freeman was still Sheriff.
  • 1988 – The County began construction on the Cudjoe Substation while William Freeman was Sheriff. Staff actually moved into the building in March, 1989, after J. Allison DeFoor became sheriff.
  • 1989 - Reserve Deputy David Cormier was the third deputy killed in the line of duty. He was killed in a vehicle accident while responding to an emergency. (Click here to go to the page for fallen deputies and more detail.)
  • 1990 - Monroe County Jail was privatized, and was turned over to Wackenhut Corrections Corporation. June 30, 1990, Sheriff J. Allison DeFoor resigned as sheriff to run as Governor Bob Martinez’s running mate. Major Richard Roth was appointed by Governor Martinez to finish DeFoor’s term. A special election was then held and Roth was elected sheriff. In December, – Sheriff’s environmental deputies tackled Stock Island. They towed 79 cars in six weeks.
  • 1991 – The jail taken back over by the Sheriff’s Office from Wackenhut because they found they couldn't make a profit.. February. First annual Pig Bowl football game between the Sheriff’s Office and Key West Police Department. President Bush and his wife, Barbara, visited the Keys. The Sheriff’s Office took over Crime Stoppers from the Coast Guard.
  • 1992 - Hurricane Andrew tore through south Florida on August 24, 1992. While the lower Keys were unaffected, the upper keys and Ocean Reef did suffer some property damage. The Sheriff’s Office sent personnel to Homestead and Florida City to assist with recovery. The County began construction on the new jail on Stock Island.
  • 1993 - New Monroe County Jail was completed on Stock Island. The ribbon cutting and cornerstone ceremonies were held November 19, 1993. The estimated cost to build the jail was $33,000,000.00. National Accreditation was allowed to lapse due to changes in the rules for Court Security. The new rules would have forced the Sheriff to replace Court Security officers with certified officers. The lower Keys District of the Sheriff’s Office acquired its first boat and started the first Sheriff’s Office Marine Unit in the Keys. Sheriff Roth accidently shot his gun off in the conference room, mortally wounding the carpet in the room. His staff had that piece of carpet framed for posterity (and to remind him to be careful with his gun). The Sheriff’s Office received a state award for his Environmental Crimes Unit.
  • 1994 - February 25, 1994, with a borrowed bus from Dade County Corrections, the inmates were moved from the old jail in Jackson Square to the new Monroe County Detention Center on Stock Island without incident. The jail on the corner of Whitehead and Fleming was closed forever. The Sheriff’s Office handled a bomb threat at the Navy’s Peary Court in Key West with ex-City Commissioner Harry Powell. Powell threatened to blow himself up because the Navy planned to build housing on the site, which the city had leased from the Navy for years and used as a park. The County began building the new Sheriff’s Headquarters building, next to the new jail on Stock Island. The Sheriff’s Office Children’s Animal Park officially opened to the public with a pony, ducks, pigs, goats and rabbits. The Culinary Arts Program, GED Program and the Art Behind Bars Program all started at the new Detention Center.
  • 1995 – The Sheriff opened a new gymnasium for employees, paid for by forfeiture funds, at the new Detention Center. The Key Largo storefront office opened to the public.
  • 1996 - The PBA began representing Corrections Officers. The Sheriff’s Office acquired a surplus Kingair 200 airplane from the military for $500 and 10 loaves of Cuban bread
  • May 3, 1998 - Deputy Michael Alexander was killed in the line of duty in a traffic accident, becoming the fourth Deputy Sheriff to die while serving the citizens of Monroe County. Deputy Michael Alexander was killed in automobile accident in Tavernier. (Click here to go to the page for fallen deputies and more detail.) In September, Hurricane Georges hit Big Pine Key causing considerable damage to the area.
  • 1999 – The Sheriff’s Office received $25 million dollars in Federal Asset Forfeiture money for its part in a long term money laundering investigation through the South Florida High Intensity Drug Trafficking Area (HIDTA). Hurricane Irene parallels the Keys to the west. An evacuation order is issued, but the Hurricane turns at the last minute, just missing the Keys.
  • 2000 - FDLE reported crime is down 12.6% in 1999 in Monroe County. Sheriff Roth formed the Sheriff’s Asset Forfeiture Fund (SAFF) with the intention of investing 15% of the 1999 $25 million forfeiture and awarding the interest in the form of grants to community organizations and charities. Islamorada and Marathon incorporated and the Sheriff’s Office signed contracts for policing with both municipalities.
  • 2001 – A groundbreaking ceremony was held at the new Department of Juvenile Justice Building, attached to the Detention Center on Stock Island. There was a multi-agency investigation into drug and gun sales which resulted in three taxi companies an one tire and auto shop being shut down. Seventeen people were arrested, including the “ringleader” Fred Ahrens and his assistant, Ron Sell. Hialeah murder suspect Alexis Quevedo hijacked a boat at Garrison Bight with a family on board. He was shot by SWAT Sniper Deputy John McGee. “Pizza Pilot” Milo Reese was taking flying lessons in Marathon and flew the plane to Cuba. In the wake of the 9/11 terrorist attacks, the Sheriff’s Office checked bridges, government buildings and other infrastructure regularly. In the wake of the anthrax poisonings, hundreds of reports of suspicious packages and suspicious “white powder” are checked by emergency services agencies in the Keys.
  • 2002 - A Car bomb went off in Marathon severely injuring a 51 year old woman. Her ex-boyfriend Gene Hodler was arrested for the crime. Trauma Star began trauma transport operations. National Accreditation was renewed. The Sheriff’s Office began offering mug shots and an offense/incident information list on the Sheriff’s web site, www.keysso.net. The Department of Juvenile Justice building was completed. A Cuban bi-plane was flown to Key West with a pilot and his family on board. The plane was subsequently seized by a woman suing the Cuban government.
  • 2003 – Sheriff Rick Roth received the “Difference Maker” award for $190,000 donated to Take Stock in Children over 4 years. A Cuban DC-3 was hijacked from Cuba and flown to Key West. The plane was subsequently seized by a woman suing the Cuban government. The Sheriff’s Office received State re-Accreditation.
  • 2004 – Hurricane Charley threatened the Florida Keys, eventually hitting Port Charlotte. Florida Keys shelters opened and some evacuations were ordered. Twelve deputies were sent to help areas affected by Hurricane Charley, along with a helicopter and mobile command post. Hurricane Frances threatened to hit the middle and upper Keys. Non-resident evacuations were ordered. Hurricane Ivan made a close approach to the Keys and, although it did stay west of the island chain, a visitor evacuation was ordered followed by a mandatory evacuation order for all residents. Hurricane Jeanne brushed by the Keys causing tropical storm winds. Shelters were opened in the Upper Keys.
  • 2005 – Immigration and Customs Enforcement (ICE) announced more money seized in the ongoing money laundering operation. The Sheriff’s Office was awarded a further $6 million for its part in the investigation, bringing the total received by the Sheriff’s Office to more than $31 million in six years. The Roth building in Plantation Key, purchased with some of the seized federal forfeiture funds, was opened for business in March. Hurricane Dennis hit the Keys in July. The Sheriff’s Office was awarded National re-Accreditation. Hurricane Katrina, predicted to hit the Miami area, made a sudden turn and hit the upper Keys in August. Hurricane Rita hit the Keys in September. Hurricane Wilma hit the Florida Keys on October 24th, flooding many homes and causing significant damage.
  • 2006 – The new Trauma Star helicopter arrived in July. The Florida Department of Law Enforcement reported crime down in Monroe County by 11.9% in 2006. Five million dollars in cocaine – 3 bundles of 30 kilos each – were found off shore of the Keys in one week. The new Trauma Star began flying with a Part 135 license allowing the county to bill for services.
  • 2007 – FDLE reports crime up 3.9% in Monroe County in 2006. At the request of the Monroe County Commission and because of budget shortages in the County, Sheriff Rick Roth delivered a zero increase budget in June. In July, at the request of the County Commission, the Sheriff offers buyouts and eliminates positions to reach a 5% cut in budget. In December, Deputy Robin Tanner died in traffic accident while responding to a medical call, becoming the fifth Monroe County Deputy to die in the line of duty. (Click here to go to the page for fallen deputies and more detail.)
  • 2009 - Robert Peryam is sworn in as the Sheriff following Rick Roth's retirement after 43 years of service.
  • 2013 - Current Sheriff, Rick Ramsay is sworn in.
  • 2017 - Hurricane Irma, rated as a category 4 storm, made landfall in the Lower Keys and caused extensive damage. This storm forced the evacuation of the main jail on the night before landfall. All the inmates and officers were transported to Palm Beach County and remained there for about three weeks.
  • May 25, 2019 - Emil LaVache, the oldest serving Deputy in the State of Florida passed away. Emil served in the Army for over 30 years, including combat in both Korea and Vietnam wars and as a full-time Deputy Sheriff for 25 years and 9 years as a Reserve Deputy. He was 88.
  • Oct. 15, 2019 - Rick Roth, the former Sheriff, passed away at the age of 80.
  • 2020 - Due to the Corona virus pandemic, the County ordered US1 coming into the Florida Keys to be restricted to residents, deliveries and essential workers only. Hotels, restaurants, bars and other tourist attractions were closed. The Sheriff's Office set up and manned a 24 hour check point on US-1 from March 27th until the County re-opened on June 1st.