Raymond McCaskey

Chairman at

Fort Dearborn Life Insurance Co.

Commercial Services

Finance

Consumer Services

Profile

Raymond Frederick McCaskey is currently Chairman at Fort Dearborn Life Insurance Co., Co-Chairman at Workforcechicago2.0, Director at Wartburg College, Director at Chicago Shakespeare Theater since 2011, Director at Life Directions, LLC, Member of The Commercial Club of Chicago, Member of The American Academy of Actuaries, Member of Society of Actuaries Research Institute, Trustee of The Lincoln Foundation for Performance Excellence, and Member of The Epilepsy Foundation of Greater Chicago.
Former positions include President & Chief Executive Officer at Health Care Service Corp., Chairman at Blue Cross & Blue Shield Association, Director at Prime Therapeutics LLC, Member of The Economic Club of Chicago (Illinois), Member of The Illinois Business Roundtable, and President at HCSC Insurance Services Co. Education includes graduate studies at DePaul University and undergraduate studies at Wartburg College.

Raymond McCaskey active positions

Companies	Position	Start
Fort Dearborn Life Insurance Co. Fort Dearborn Life Insurance Co. Insurance Brokers/ServicesFinance Provides group life, disability insurance services and products	Chairman	-
The American Academy of Actuaries The American Academy of Actuaries Miscellaneous Commercial ServicesCommercial Services Operates as a professional membership association for retirement planning and social scrutiny	Corporate Officer/Principal	-
The Society of Actuaries The Society of Actuaries Miscellaneous Commercial ServicesCommercial Services Operates as a professional organization for actuaries	Corporate Officer/Principal	-
The Lincoln Foundation for Performance Excellence	Director/Board Member	-
The Commercial Club of Chicago The Commercial Club of Chicago Miscellaneous Commercial ServicesCommercial Services Operates as a membership organization	Corporate Officer/Principal	-
Workforcechicago2.0	Chairman	-
The Epilepsy Foundation of Greater Chicago The Epilepsy Foundation of Greater Chicago Miscellaneous Commercial ServicesCommercial Services Operates as a non profit organization that promotes awareness and understanding, advocating for laws that matter to people with epilepsy and funding epilepsy research	Corporate Officer/Principal	-
Life Directions, LLC Life Directions, LLC Life Directions, LLC is a nonprofit organization dedicated to supporting at-risk youth and young adults, primarily aged 13 to 35, in poverty-impacted communities. The private company is based in Chicago, IL. Its core initiatives include the Peer Mentor Program, which trains 10th and 11th graders to mentor 8th graders transitioning to high school; the Peer Motivation Program, engaging high school students in peer-led discussions and community service; the Neighborhood Enrichment Program, which mobilizes young adults and volunteers to reduce community violence through intergenerational peer organizing; and the Focus Family Program, providing trauma-informed support and resources to youth and families affected by trauma and COVID-19. Life Directions emphasizes relationship building, cultural competence, social-emotional learning, and community service to promote academic success, personal growth, and healing. Founded in 1973 in response to youth violence, the organization focuses on fostering self-responsibility, leadership, and positive peer relationships through interconnected, evidence-based programs.	Director/Board Member	-
Chicago Shakespeare Theater Chicago Shakespeare Theater Movies/EntertainmentConsumer Services Operates performance theaters	Director/Board Member	-
░░░░░░░░ ░░░░░░░	░░░░░░░░░░░░░░ ░░░░░░	-

All active positions of Raymond McCaskey

Former positions of Raymond McCaskey

Companies	Position	End
░░░░ ░░░░░░░░░ ░░░░░░░░ ░░░	░░░░░░░░░	-
░░░░ ░░░░░ ░░░░░ ░░░░ ░░░░░░ ░░░░░░░░░░░	░░░░░░░░	-
░░░ ░░░░░░░░ ░░░░ ░░ ░░░░░░░ ░░░░░░░░░░	░░░░░░░░░ ░░░░░░░░░░░░░░░░░	-
░░░░░ ░░░░░░░░░░░░ ░░░	░░░░░░░░░░░░░░ ░░░░░░	-
░░░ ░░░░░░░░ ░░░░░░░░ ░░░░░░░░░░	░░░░░░░░░ ░░░░░░░░░░░░░░░░░	-

See the detail of Raymond McCaskey's experience

Training of Raymond McCaskey

Experiences
Positions held

Active

Inactive

Listed companies

Private companies

See the detail of Raymond McCaskey's experience

Connections

1st degree connections

1st degree companies

Male

Female

Members of the board

Executives

See the personal network

Linked companies

Private companies	17
Health Care Service Corp. Health Care Service Corp. Life/Health InsuranceFinance Provides health plans, third-party administrators, organization and government entity services	Finance
Fort Dearborn Life Insurance Co. Fort Dearborn Life Insurance Co. Insurance Brokers/ServicesFinance Provides group life, disability insurance services and products	Finance
Prime Therapeutics LLC Prime Therapeutics LLC Managed Health CareHealth Services Operates as pharmacy benefit management firm	Health Services
DePaul University DePaul University Other Consumer ServicesConsumer Services Functions as a College/University	Consumer Services
Wartburg College Wartburg College Other Consumer ServicesConsumer Services Functions as a College/University	Consumer Services
Blue Cross & Blue Shield Association Blue Cross & Blue Shield Association Miscellaneous Commercial ServicesCommercial Services Operates as an association of health insurance companies	Commercial Services
The Commercial Club of Chicago The Commercial Club of Chicago Miscellaneous Commercial ServicesCommercial Services Operates as a membership organization	Commercial Services
The American Academy of Actuaries The American Academy of Actuaries Miscellaneous Commercial ServicesCommercial Services Operates as a professional membership association for retirement planning and social scrutiny	Commercial Services
The Economic Club of Chicago (Illinois) The Economic Club of Chicago (Illinois) Miscellaneous Commercial ServicesCommercial Services Engages in fostering connections among leaders to encourage dialogue on important economic and social issues	Commercial Services
The Society of Actuaries The Society of Actuaries Miscellaneous Commercial ServicesCommercial Services Operates as a professional organization for actuaries	Commercial Services
Chicago Shakespeare Theater Chicago Shakespeare Theater Movies/EntertainmentConsumer Services Operates performance theaters	Consumer Services
The Lincoln Foundation for Performance Excellence
The Illinois Business Roundtable The Illinois Business Roundtable The Illinois Business Roundtable operated as a voluntary association of chief executive officers. The company was headquartered in Chicago, IL.
HCSC Insurance Services Co. HCSC Insurance Services Co. Multi-Line InsuranceFinance Provides life and health insurance services	Finance
Workforcechicago2.0
The Epilepsy Foundation of Greater Chicago The Epilepsy Foundation of Greater Chicago Miscellaneous Commercial ServicesCommercial Services Operates as a non profit organization that promotes awareness and understanding, advocating for laws that matter to people with epilepsy and funding epilepsy research	Commercial Services
Life Directions, LLC Life Directions, LLC Life Directions, LLC is a nonprofit organization dedicated to supporting at-risk youth and young adults, primarily aged 13 to 35, in poverty-impacted communities. The private company is based in Chicago, IL. Its core initiatives include the Peer Mentor Program, which trains 10th and 11th graders to mentor 8th graders transitioning to high school; the Peer Motivation Program, engaging high school students in peer-led discussions and community service; the Neighborhood Enrichment Program, which mobilizes young adults and volunteers to reduce community violence through intergenerational peer organizing; and the Focus Family Program, providing trauma-informed support and resources to youth and families affected by trauma and COVID-19. Life Directions emphasizes relationship building, cultural competence, social-emotional learning, and community service to promote academic success, personal growth, and healing. Founded in 1973 in response to youth violence, the organization focuses on fostering self-responsibility, leadership, and positive peer relationships through interconnected, evidence-based programs.