Jim began his career in Law Enforcement in 1974, when he entered the State Police Academy in Framingham. After assignments as a uniformed trooper out of the Framingham Barracks and State Police Logan Airport, he was assigned to investigate organized crime in the Boston and South Shore areas. In 1977, he transferred to the Crime Prevention and Control Unit (CPAC), attached to the Office of Cape and Islands District Attorney Phillip A. Rollins. During his many years at this assignment, Jim became a court-qualified expert in matters relating to Organized Crime/Gaming, Narcotics and Arson. He also coordinated and taught at the first homicide school ever offered at the Massachusetts State Police Academy. Jim retired as the Detective lieutenant in charge of the State Police Detectives covering Barnstable, Dukes and Nantucket Counties.

Since being sworn in to his first term of office on January 6, 1999, Sheriff Cummings has made many changes within the organization to enhance the professionalism of law enforcement staff. Every correctional officer employed by the Sheriff’s Office must meet strict hiring standards including a written examination, physical fitness test and oral review. Individuals found to meet these standards attend a specialized eight-week training academy that combines classroom lecture with physical fitness training. The first promotional examination process was also introduced for current employees to ensure law enforcement staff continue their careers with the same momentum of which they began. To further increase public safety within Barnstable County, Sheriff Cummings expanded the K9 Unit and the Bureau of Criminal Investigation, started a Warrant Apprehension Unit with state and local police, and converted the former Sheriff’s residence to badly needed office space.

Sheriff Cummings has also undertaken youth prevention programs as a priority. The Sheriff’s Youth Ranch is home to the Sheriff’s Youth academy, a twelve-week program for Barnstable County Youth. Teachers, police officers and parents recommend the youth for the program. The mission of the program is to empower individuals, families and communities to stop violence, substance abuse, delinquency, and crime, thereby preventing adult incarceration by meeting developmental needs positively through effective prevention/intervention services. In addition to the Youth Academy, Sheriff Cummings initiated an Out of School Suspension Program, Inside Program and Outdoor Challenge Ropes Course. In recognition of the strides made to address at-risk youth within Barnstable County, Sheriff Cummings was appointed to the National Sheriffs Association’s Committee for Youth Programs and Juvenile Justice.

The Sheriff has also brought TRIAD to Barnstable County. This program puts the senior population, the local police and the Sheriff together to solve problems with and for the senior community. 12 towns have signed TRIAD agreements and Sheriff Cummings hopes to have all fifteen towns involved with TRIAD.

• January 9, 1998 - Certificate of Appreciation of the Drug Enforcement Administration under the United States Department of Justice for outstanding contributions in the field of drugs and law enforcement, presented to James Cummings in his role as Detective Lieutenant for the Massachusetts State Police Department in gratitude for superior contributions to the law enforcement responsibilities of the United States Secret Service

• March 17, 1999 - Recognition by the Cape & Islands Emergency Medical Services for participating in the Second Annual Public Safety Telecommunicators Training Seminar held at Cape Cod Community College

• Mar.-June 1999 - Barnstable Fatherhood Program.... in recognition of support and involvement in promoting responsible fatherhood principles in the Barnstable Fatherhood Program . . signed by Probation Officers J. Robert Smith and Joseph D. Casey, Jr.

• October 4, 1999 - Barnstable County Triad Appreciation Award for assistance with the first Barnstable County Triad Conference

• November 22, 1999 - American Jail Association recognizes him as a professional member

• YMCA, 2000 Appreciation for your contribution to YMCA of Cape Cod 2000 Reach Out for the Youth Campaign

• March 4, 2000 - Certificate of Appreciation, through the local brotherhood of Police Officers in recognition for technical support first in Cumming’s role as State Police Lieutenant and also as Sheriff of Barnstable County

• April 29, 2000 - MADD (Mothers Against Drunk Drivers) Appreciation for Support of MADD’s Youth in Action Programs

• ESGR, 2000 Employee Support of the Guard and Reserve...Certificate of Appreciation on behalf of the men and women of America’s Reserve Forces for outstanding service to the national defense through continuing support of the National Guard and Reserve.

• July 6, 2000 - Yarmouth Housing Authority....Certificate of Appreciation in recognition of outstanding service to the Housing Authority and Board of Commissioners for efficient use of tax dollars through the use of inmates labor for public purposes (received this 4/10/00)

• August 1, 2000 - Professional Assistance Aware and Certificate of Appreciation by the Falmouth Police Department for working in partnership with Falmouth Police Department to reduce crime, increase public safety and improve the overall quality of life in the Town of Falmouth, issued by Chief of Police David Cusilito

• November 9, 2000 - Dennis Housing Authority....with sincere appreciation for your belief in giving back to the Community for the many benefits we received from the Community Service Work Program

• 2000 International Association of Police Chiefs....issued certificate of membership of the IAPC dedicated to the advancement of professionalism and law enforcement

• January 19, 2001 - received Citation from Massachusetts House of Representatives signed by Speaker of House Thomas Finneran in recognition of leadership, performance and personal example to advance the welfare of the Cape Cod Canal Region Chamber of Commerce and the Community

• January 19, 2001 - received Citation from Massachusetts Senate, signed by President of the Senate, Thomas Birmingham for the same

• 2001 Recipient of the Regional Service Award presented by the Cape Cod Canal Region Chamber of Commerce to an individual whose leadership, performance, personal example and good influence has done the most to advance the welfare of the Chamber of Commerce and the Community

• Sept. 2002 - In recognition of outstanding commitment and continued support for 32nd Bourne Scallop Festival, given by the Cape Cod Canal Chamber of Commerce, which includes the communities of Bourne, Sandwich and Wareham

• Sept. 2002 - Muscular Dystrophy Association...valued supporter in the effort to find treatments ane cures for neuromuscular diseases

• January 2003 - Vice-President and President Elect of the Massachusetts Sheriff's Association

• May 2003 - East Coast Regional Conference, Falmouth. In recognition for continued support of APCO and 2003 East Coast Regional Conference

• June 2003 - Member of the new Massachusetts Military Reservation Military-Civilian Community Council, an advisory board formed to promote goodwill and unity between the Massachusetts National Guard, military and civilian tenants of the MMR and local and regional communities and organizations.

•September 2003 - Appointed Executive Board member of the Governor's Commission on Criminal Justice Innovation

•October 1, 2003 - Certificate of Recognition for Leadership on the Barnstable County TRIAD Project from the Bourne Women's Club

•October 2003 - Leadership Award from the Cape Cod Council on Alcoholism