About Craig Cunningham
Craig Cunningham is a Managing Director, Wealth Management, Financial Advisor and Senior Portfolio Management Director with the Southwest Legacy Group at Morgan Stanley. A third-generation financial advisor with over 27 years of experience, Craig delivers thoughtful, values-driven guidance to affluent individuals and multigenerational families as they navigate life’s most meaningful financial decisions.
A graduate of Eastern Illinois University with a degree in Economics, Craig began his career with Morgan Stanley in 1995 — and has remained with the firm ever since. That long-standing tenure speaks not only to his long-term commitment to clients, but also his dedication to continuous professional growth. Over the years, he has evolved from a solo financial advisor into a seasoned leader, mentor, and co-founder of the Southwest Legacy Group. Along the way, he also earned Morgan Stanley’s highest designation for portfolio management, Senior Portfolio Management Director. Grounded in the belief that every dollar invested can and should reflect a client’s values, Craig leverages this designation to help clients align their portfolios with their unique vision for their retirement, family, and broader community.
Today, Craig and his team are known for delivering a truly comprehensive wealth management service that integrates investment strategy with estate planning, tax efficiency, and business succession guidance. With a deep understanding of both financial markets and family dynamics, he plays a central role in managing the team’s investment strategy, helping to bring clarity and intention to highly complex financial lives — and often acting as a central steward across generations. His investment approach is grounded in discipline, tax awareness, and long-term vision, but it is equally shaped by the priorities and aspirations of the families he serves. As a third-generation financial advisor, Craig has seen firsthand the impact that financial knowledge can have across a family’s legacy, which is why he’s passionate about equipping the next generation with the tools and perspective to carry wealth forward with purpose. Whether navigating a liquidity event, transitioning a business, or coordinating with clients’ legal and tax advisors, Craig strives to remain a thoughtful, steady presence for decades to come — helping clients protect what they’ve built and plan for the legacy they want to leave.
Outside the office, Craig has long been committed to giving back — coaching youth sports, volunteering with local service leagues, mentoring young professionals and contributing to area schools. A former member of the Family Advisor Alliance with Advocate Hospital, he long served as a passionate guide for families navigating childhood cancer diagnoses. When he’s not working with clients, you’ll likely find him golfing, mountain biking, or traveling with his wife, Melissa, and their four children.
Securities Agent: AZ, WA, KY, AR, VT, IN, GA, TN, OH, MN, KS, DE, NM, MO, NY, NV, ND, NC, IL, NJ, CA, SC, ID, IA, WI, VA, MI, MD, NE, PA, NH, DC, CT, CO, AL, TX, PR, MS, MA, FL; General Securities Representative; Investment Advisor Representative; Managed Futures
NMLS#: 1265049
AR Insurance License #: 759856