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Charles County Sheriff's Office

CCSO Lt. Colonel Robert Cleaveland to Retire

Lt. Colonel Robert Cleaveland

Lt. Colonel Robert Cleaveland

Charles County, MD …. Lieutenant Colonel Robert Cleaveland, a 30-year-veteran of the Charles County Sheriff’s Office, will retire on Saturday, January 31. Known for his leadership, incredible knowledge of Agency policies, and compassion for victims of crime, Lt. Colonel Cleaveland had what he calls “an amazing career working with the men and women of the Sheriff’s Office and serving the citizens of Charles County.”

Lt. Colonel Cleaveland was born in Washington, DC. michael kors outlet online His father was a professional truck driver and his mother was a teaching assistant in Charles County, working with special needs children. After high school, he began working in construction. In 1983, Cleaveland was hired as an arson investigator with the Maryland State Fire Marshal’s Office and received his training from the Prince George’s County Police Academy. In 1985, his work led him to the Charles County Sheriff’s Office, where he was hired as a police officer. He rose through the ranks and ultimately in 2014 was appointed Chief Assistant Sheriff, serving as second-in-command of more than 600 sworn, corrections, and civilian employees until his retirement. “Lieutenant Colonel Robert Cleaveland has dedicated thirty years of his life to this Agency and to the safety of the citizens of Charles County. He had a successful career that spanned many facets of the Agency, culminating in his appointment as the highest ranking administrative and supervisory authority at the Sheriff’s Office,” said Sheriff Troy D. Berry. “He was instrumental in ensuring a smooth transition when I took office, for which he has earned my deep appreciation. More importantly, he is a caring family man. On behalf of everyone at the Charles County Sheriff’s Office, I wish him all the best in his retirement.”

When Lt. Colonel Cleaveland began his career with the CCSO, he was assigned to Patrol Operations and worked as a patrol officer. In 1987, he was transferred to the Criminal Investigations Division where he handled investigations ranging from thefts to homicide. In 1992, he was trained as a polygraph examiner and conducted both pre-employment and criminal examinations. In 1993, Cleaveland was promoted to Sergeant and remained in CID as a supervisor of the Child Abuse Unit. In 1996, he was transferred to the Internal Affairs Division, where he worked for five years. In 2001, he moved to the Pre-Employment Section, overseeing background investigations for prospective employees. In 2003, he was promoted to Lieutenant and served as a Patrol Operations Commander and then as the District II, Indian Head Commander. In 2006, Cleaveland was promoted to Captain and served as the Commander of Executive Services. In that position, Cleaveland was responsible for supervising the Office of Planning and Accreditation, Media Relations, Safety & Inspections, and the Criminal Justice Program at North Point High School. In 2011, Cleaveland was promoted to the rank of Major and served as the Assistant Sheriff of Operations. In 2014, he was appointed as Chief Assistant Sheriff and promoted to the rank of Lt. Colonel.

Lt. Colonel Cleaveland received many awards and letters of appreciation throughout his career. In May 1990, he was selected as one of two Officers of the Year by the Americanism Committee of the Voiture Locale #456 for his outstanding investigative skills as the lead investigator of several violent crimes that occurred in 1989, an unusually busy year for detectives assigned to the Criminal Investigations Division.

During that time, Detective Cleaveland solved the murder of a man whose body was not discovered until days after he was killed. With no solid leads, Cleaveland dedicated hundreds of hours – including many off-duty evenings and weekends – tracking down the killer. As a result of his tenacity, the suspect was identified and later convicted. Cleaveland was also recognized by Frank Jones, the Assistant State’s Attorney at that time, for his exceptional preparation for the trial.

Later in 1989, Detective Cleaveland was assigned to investigate the brutal sexual assault of a fourth-grade girl who was attacked at her elementary school. He linked her case to similar cases in Washington, DC, and Virginia. As a result, a suspect was identified and convicted.

Also that same year, Detective Cleaveland was assigned a robbery case that occurred in Charles County. He identified a suspect and subsequently developed information that the suspect had knowledge of a triple murder in Prince George’s County. Working closely with members of the Prince George’s County Police Department’s Homicide Unit, investigators later identified the suspects involved in the killings at Stoney’s Restaurant in Clinton, MD.

In December 1989, Detective Cleaveland received the agency’s Meritorious Award for saving the life of a suicidal man who had been committed to the hospital. While in custody, the man broke free from his restraints, destroyed the hospital room, and broke apart a wooden bed, using a section of the frame to break a second-story window. He climbed out of the window and eventually made his way to the edge of the snow-covered roof where he threatened to jump. During his escape, he threw pieces of the bed at hospital personnel and threatened anyone who came near him. Cleaveland responded and positioned himself at the foot of the hospital, directly underneath the man. He was able to develop a rapport with the subject and eventually convinced the man to walk away from the edge, saving his life.

Cleaveland was also recognized for his work during the 2002 tornado that devastated the town of La Plata. He and many others worked countless hours during several weeks in stabilizing the area and coordinating recovery efforts of our community.

Letters of Appreciation include recognition for his work overseeing police operations during the grand-opening of Regency Furniture Stadium and the first professional baseball game for the Southern Maryland Blue Crabs; his participation in promotional boards for outside law enforcement agencies; his numerous contributions to the Christmas in April program; lectures at the Charles County Community College (now CSM); classroom instruction relating to Code of Ethics, vehicle skills, and arson investigation at the Southern Maryland Criminal Justice Academy; polygraph examinations; and his compassion for victims of crime and their families.

Perhaps the most notable and proudest achievement for Lt. Colonel Cleaveland is his role as the father of triplets – a girl and two boys. Born in 1992 at 29 weeks, the triplets spent the first few months of their lives in the hospital. Today, they are 22-years-old and thriving in their independent lives. His daughter, Sara, is preparing to graduate from Flagler College with a Bachelor of Arts degree in graphic design. One son, Shane, is in the US Navy; another son, Christopher, is in the US Air Force stationed in Little Rock, Arkansas. He serves as crew chief for C-130s attached to a training squadron.

In his spare time, Lt. Colonel Cleaveland serves as a volunteer firefighter of more than 20 years at the Waldorf Fire Department, where he was past Deputy Chief and Assistant Chief. He and his wife also owned and operated a trucking company for 12 years while their children were young.

Lt. Colonel Cleaveland has been married to his wife, Marylou, for 26 years. Upon retiring, Cleaveland said he will “relax and complete a few items on his honey-do list.” He plans to explore some part-time opportunities and travel with his wife, visiting their children wherever life takes them.

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