Meet Jeff Cragg

Qualified Like No Other Candidate

Jeff Cragg for Insurance Commissioner Press ConferenceProfessional Experience

Insurance Industry Experience – 24 years Insurance Company Management Experience in ever increasing positions of responsibility. Worked for Northwestern National Life, Mutual of Omaha, Provident Indemnity Life, Employers Reinsurance (wholly owned subsidiary of General Electric), A-G Administrators, Inc. and Academic Risk, Inc.

Management Experience in:

Sales, Marketing, Administrative Management, Claims Operations, and Reinsurance.

Job Titles:

Field Representative, Director of Sales, Vice President Sales, Vice President – Group Operations, Executive Vice President, Reinsurance Treaty Representative.

Served as a Principal Officer of an Insurance Company, as well as, an Officer of the Parent Insurance Company Holding Company listed on the NASDAQ Exchange.

Small Business Owner/Operator Experience – Acquired Mailboxes, Etc. location in N. Wilmington in 2000, own it with Terry Cragg, spouse and business partner. Store is now re-branded as MY MAILBOX STORE since 2014.

Services provided to the Community:

Shipping with ALL the major carriers: UPS, FedEx, and USPS.

FAX, Scanning, Packaging, Copies, Mailbox Rental, Notary Services.

My Mailbox Store is entering its 30th year of operations, 25th year at the same location, 21st year owned by Terry and Jeff

Family Background

Family Man – Husband/Father 2020 is our 29th Wedding Anniversary, proud father of a family of 4

Chase, the oldest son, Brandywine HS graduate, University of Delaware graduate ( Captain of the Golf Team), Widener School of Law graduate. Practicing Attorney in Delaware specializing in Bankruptcy.

Tyler, Second son, Brandywine HS graduate, Carleton College, graduate, graduate  Washington & Lee University College of Law. Employed by a large Delaware Law Firm.

Madison, Daughter, Brandywine HS graduate, graduate Randolph-Macon College with a BA in Business/Economics. Working towards her CPA at Virginia Commonwealth University.

Grant, Youngest Son, graduate Sanford School, Hockessin, DE.  Junior at University of Mary Washington, Fredericksburg, VA.  Member of the Varsity Men’s Lacrosse team.  Majoring in Digital Studies and Communications, expected graduation 2022.

Terry, Spouse, Delaware Native, former Insurance Company Manager in Group Administration, supervised over 150 employees, mother of 4, Owner/Operator My Mailbox Store, formerly Mailboxes Etc., since 2000, entering its 21st year of profitable operations under her leadership.


New Trier Township HS Winnetka, IL graduate 1979. Illinois State Scholar, Member Varsity Fencing Team, Illinois State Champions 1979.

Carleton College, Northfield, MN. Graduated 1983 BA in Economics, Member Varsity Football Team, Defensive Tackle

Northwestern University, Summer classes in Marketing

University of Pennsylvania, Evening classes in Finance

Life Office Management Association, FLMI, Fellow, Life Management Institute, completion of 10 University level courses in Insurance Company Management

Academy of Life Underwriting, AALU Associate Academy of Life Underwriting Designation and Diploma

Community Involvement

President, Woodbrook Civic Association, New Castle County Delaware

President, Sea Chase Condominium Association Rehoboth Beach Delaware

Political Experience

Member, New Castle County Board Of Elections

Co-Chairman, New Castle County Republican Committee

Treasurer, New Castle County Republican Committee

Member Republican State Executive Committee

2004 Delegate Republican National Convention New York, NY

2005 Candidate Republican State Committee Chairman

2012 Republican Candidate for Governor, State of Delaware

2016 Republican Candidate for Insurance Commissioner, State of Delaware