About

Chris

About Chris

Professional Background

Christopher L. Gandy is the Founder and CEO of Midwest Legacy Group, a boutique concierge insurance firm established in 2010. The firm serves high-net-worth clients—including executives, professional athletes, physicians, business owners, and entrepreneurs—focusing on wealth accumulation, preservation, retirement strategies, insurance, asset protection, and investments. Through his work, Gandy has built a reputation for personalized, relationship-driven service that helps clients achieve long-term financial success.

Professional Background

Christopher L. Gandy is the Founder and CEO of Midwest Legacy Group, a boutique concierge insurance firm established in 2010. The firm serves high-net-worth clients—including executives, professional athletes, physicians, business owners, and entrepreneurs—focusing on wealth accumulation, preservation, retirement strategies, insurance, asset protection, and investments. Through his work, Gandy has built a reputation for personalized, relationship-driven service that helps clients achieve long-term financial success.

Athletic & Early Career

A former professional basketball player, Gandy played for the Chicago Bulls, the San Antonio Spurs, and internationally in France, following a standout collegiate career at the University of Illinois. In 1999, he transitioned into financial services, beginning with Northwestern Mutual Financial Network, later founding APEX Consulting Group LLC, and serving as Senior Vice President of Sales at MassMutual Chicago. His unique background as a professional athlete provides him with a deep understanding of the financial challenges faced by high-income earners, particularly athletes.

Athletic & Early Career

A former professional basketball player, Gandy played for the Chicago Bulls, the San Antonio Spurs, and internationally in France, following a standout collegiate career at the University of Illinois. In 1999, he transitioned into financial services, beginning with Northwestern Mutual Financial Network, later founding APEX Consulting Group LLC, and serving as Senior Vice President of Sales at MassMutual Chicago. His unique background as a professional athlete provides him with a deep understanding of the financial challenges faced by high-income earners, particularly athletes.

Leadership, Advocacy & NAIFA Involvement

Gandy has been an active member of the National Association of Insurance and Financial Advisors (NAIFA) since 2003. He has held numerous leadership roles, including President of NAIFA-Chicagoland and member of NAIFA’s Strategic Planning Committee. Recognized with the NAIFA Diversity Champion Award in 2022, Gandy is a committed advocate for diversity and inclusion in the financial services profession.

He is currently serving as NAIFA’s President-Elect for the 2025–2026 term and
will assume the presidency in January 2026.   

In this role, he collaborates with the current President, Board of Trustees, and executive leadership to shape strategic priorities, advance the profession, and guide future initiatives. He is also known for mentoring the next generation of financial advisors and emphasizing the importance of relationship-building and community engagement.

Leadership, Advocacy & NAIFA Involvement

Gandy has been an active member of the National Association of Insurance and Financial Advisors (NAIFA) since 2003. He has held numerous leadership roles, including President of NAIFA-Chicagoland and member of NAIFA’s Strategic Planning Committee. Recognized with the NAIFA Diversity Champion Award in 2022, Gandy is a committed advocate for diversity and inclusion in the financial services profession.

He is currently serving as NAIFA’s President-Elect for the 2025–2026 term and
will assume the presidency in January 2026.   

In this role, he collaborates with the current President, Board of Trustees, and executive leadership to shape strategic priorities, advance the profession, and guide future initiatives. He is also known for mentoring the next generation of financial advisors and emphasizing the importance of relationship-building and community engagement.

Community & Philanthropy

Beyond his professional endeavors, Gandy is dedicated to financial literacy and community empowerment. He supports initiatives that expand financial education, particularly in underserved communities, and serves on boards such as the Chicago Concussion Coalition and The Urban League. Through speaking engagements, interviews, and mentorship, he encourages individuals and communities to achieve financial independence while addressing systemic barriers to wealth-building.

Community & Philanthropy

Beyond his professional endeavors, Gandy is dedicated to financial literacy and community empowerment. He supports initiatives that expand financial education, particularly in underserved communities, and serves on boards such as the Chicago Concussion Coalition and The Urban League. Through speaking engagements, interviews, and mentorship, he encourages individuals and communities to achieve financial independence while addressing systemic barriers to wealth-building.