Craig Cunningham
Managing Director, Wealth Management,
Financial Advisor,
Senior Portfolio Management Director
Direct:
(708) 226-5478(708) 226-5478
Toll-Free:
(800) 323-1340(800) 323-1340
My Mission Statement
Providing comprehensive solutions for high-net worth individuals and families focusing on legacy planning and multigenerational wealth. I utilize modern planning techniques and investment technology to build customized investment strategies for each individual client.
My Story and Services
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.
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.
Services Include
- Trust AccountsFootnote1
- Alternative InvestmentsFootnote2
- Financial PlanningFootnote3
- Professional Portfolio ManagementFootnote4
- Wealth ManagementFootnote5
- Wealth PlanningFootnote6
- Estate Planning StrategiesFootnote7
- Retirement PlanningFootnote8
- Long-term Care InsuranceFootnote9
- Divorce Financial AnalysisFootnote10
- 401(k) Rollovers
- AnnuitiesFootnote11
Securities Agent: MS, IA, WA, NE, KY, AR, WI, VA, MT, MI, MD, NY, NV, NC, IL, TX, MA, FL, AZ, TN, OH, MN, KS, DE, NM, MO, NJ, CA, PA, NH, DC, CT, CO, AL, VT, IN, GA, SC, ID; General Securities Representative; Investment Advisor Representative; Managed Futures
NMLS#: 1265049
AR Insurance License #: 759856
NMLS#: 1265049
AR Insurance License #: 759856
Check the background of Our Firm and Investment Professionals on FINRA's BrokerCheck.*
Location
15341 S. 94th Ave
Ste 200
Orland Park, IL 60462
US
Direct:
(708) 226-5478(708) 226-5478
Toll-Free:
(800) 323-1340(800) 323-1340
Fax:
(708) 226-5444(708) 226-5444
Wealth Management
Global Investment Office
Portfolio Insights
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Financial Wellness
Enhancing Financial Wellness enables your workforce to do their best work. Companies that invest in financial wellness have an opportunity to:
- Reduce employee stress,
- Improve retention and engagement, and
- Set themselves apart by offering comprehensive financial wellness benefits.
Ready to start a conversation? Contact Craig Cunningham today.
1Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning and other legal matters.
For more information, please see the Morgan Stanley Smith Barney LLC Client Relationship Summary.
2Alternative Investments are speculative and include a high degree of risk. An investor could lose all or a substantial amount of his/her investment. Alternative investments are appropriate only for qualified, long-term investors who are willing to forgo liquidity and put capital at risk for an indefinite period of time.
3Morgan Stanley offers a wide array of brokerage and advisory services to its clients, each of which may create a different type of relationship with different obligations to you. Please consult with your Financial Advisor to understand these differences or review our Understanding Your Brokerage and Investment Advisory Relationships brochure available at www.morganstanley.com/wealth-relationshipwithms/pdfs/understandingyourrelationship.pdf.
4Morgan Stanley’s investment advisory programs may require a minimum asset level and, depending on your specific investment objectives and financial position, may not be appropriate for you. Please see the Morgan Stanley Smith Barney LLC program disclosure brochure (the “Morgan Stanley ADV”) for more information in the investment advisory programs available. The Morgan Stanley ADV is available at www.morganstanley.com/ADV.
5Morgan Stanley Wealth Management is the trade name of Morgan Stanley Smith Barney LLC, a registered broker-dealer in the United States. Morgan Stanley Wealth Management is a business of Morgan Stanley Smith Barney LLC.
6Morgan Stanley offers a wide array of brokerage and advisory services to its clients, each of which may create a different type of relationship with different obligations to you. Please consult with your Financial Advisor to understand these differences or review our Understanding Your Brokerage and Investment Advisory Relationships brochure available at www.morganstanley.com/wealth-relationshipwithms/pdfs/understandingyourrelationship.pdf.
Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
7Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning and other legal matters.
8When Morgan Stanley Smith Barney LLC, its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors (collectively, “Morgan Stanley”) provide “investment advice” regarding a retirement or welfare benefit plan account, an individual retirement account or a Coverdell education savings account (“Retirement Account”), Morgan Stanley is a “fiduciary” as those terms are defined under the Employee Retirement Income Security Act of 1974, as amended (“ERISA”), and/or the Internal Revenue Code of 1986 (the “Code”), as applicable. When Morgan Stanley provides investment education, takes orders on an unsolicited basis or otherwise does not provide “investment advice”, Morgan Stanley will not be considered a “fiduciary” under ERISA and/or the Code. For more information regarding Morgan Stanley’s role with respect to a Retirement Account, please visit www.morganstanley.com/disclosures/dol. Tax laws are complex and subject to change. Morgan Stanley does not provide tax or legal advice. Individuals are encouraged to consult their tax and legal advisors (a) before establishing a Retirement Account, and (b) regarding any potential tax, ERISA and related consequences of any investments or other transactions made with respect to a Retirement Account. Individuals should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
9Insurance products are offered in conjunction with Morgan Stanley Smith Barney LLC’s licensed insurance agency affiliates.
10Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
11Annuities are offered in conjunction with Morgan Stanley Smith Barney LLC’s licensed insurance agency affiliates.
Check the background of our Firm and Investment Professionals on FINRA's BrokerCheck*.
The information, products and services described here are intended only for individuals residing in states where this Financial Advisor is properly registered as described in this site.
Morgan Stanley reserves the right, to the extent permitted under applicable law, to retain and monitor all electronic communications. Morgan Stanley will not accept purchase or sale orders via any Internet site, social media site and/or its messaging systems. Morgan Stanley does not endorse and is not responsible and assumes no liability for content, products or services posted by third-parties on any Internet site, social media site and/or its messaging systems. All electronic communications are subject to terms available at the following link:
https://www.morganstanley.com/disclaimers/mswm-email.html. Any profiles and associated content are for U.S. residents only.
The securities/instruments, services, investments and investment strategies discussed in this material may not be appropriate for all investors. The appropriateness of a particular investment, investment strategy or service will depend on an investor's individual circumstances and objectives. Morgan Stanley Smith Barney LLC recommends that investors independently evaluate particular investments, strategies and services, and encourages investors to seek the advice of a Financial Advisor or Private Wealth Advisor. This material does not provide individually tailored investment advice. It has been prepared without regard to the individual financial circumstances and objectives of persons who receive it.
Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors or Private Wealth Advisors do not provide tax or legal advice. Individuals should consult their tax advisor for matters involving taxation and tax planning and their attorney for legal matters.
Morgan Stanley Smith Barney LLC (“Morgan Stanley”) is not implying an affiliation, sponsorship, endorsement with/of the third party or that any monitoring is being done by Morgan Stanley of any information contained within the website. Morgan Stanley is not responsible for the information contained on the third-party website or the use of or inability to use such site. Nor do we guarantee their accuracy or completeness.
The views, opinions or advice contained within third party websites or materials are solely those of the author, who is not a Morgan Stanley employee, and do not necessarily reflect those of Morgan Stanley Smith Barney LLC, or its affiliates. The strategies and/or investments referenced may not be appropriate for all investors as the appropriateness of a particular investment or strategy will depend on an investor's individual circumstances and objectives.
*References to length of service at Morgan Stanley include years at Morgan Stanley and predecessor firms.
Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization's initial and ongoing certification requirements to use the certification marks.
The use of the CDFA designation does not permit the rendering of legal advice by Morgan Stanley or its Financial Advisors which may only be done by a licensed attorney. The CDFA designation is not intended to imply that either Morgan Stanley or its Financial Advisors are acting as experts in this field.
Awards Disclosures | Morgan Stanley
For more information, please see the Morgan Stanley Smith Barney LLC Client Relationship Summary.
2Alternative Investments are speculative and include a high degree of risk. An investor could lose all or a substantial amount of his/her investment. Alternative investments are appropriate only for qualified, long-term investors who are willing to forgo liquidity and put capital at risk for an indefinite period of time.
3Morgan Stanley offers a wide array of brokerage and advisory services to its clients, each of which may create a different type of relationship with different obligations to you. Please consult with your Financial Advisor to understand these differences or review our Understanding Your Brokerage and Investment Advisory Relationships brochure available at www.morganstanley.com/wealth-relationshipwithms/pdfs/understandingyourrelationship.pdf.
4Morgan Stanley’s investment advisory programs may require a minimum asset level and, depending on your specific investment objectives and financial position, may not be appropriate for you. Please see the Morgan Stanley Smith Barney LLC program disclosure brochure (the “Morgan Stanley ADV”) for more information in the investment advisory programs available. The Morgan Stanley ADV is available at www.morganstanley.com/ADV.
5Morgan Stanley Wealth Management is the trade name of Morgan Stanley Smith Barney LLC, a registered broker-dealer in the United States. Morgan Stanley Wealth Management is a business of Morgan Stanley Smith Barney LLC.
6Morgan Stanley offers a wide array of brokerage and advisory services to its clients, each of which may create a different type of relationship with different obligations to you. Please consult with your Financial Advisor to understand these differences or review our Understanding Your Brokerage and Investment Advisory Relationships brochure available at www.morganstanley.com/wealth-relationshipwithms/pdfs/understandingyourrelationship.pdf.
Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
7Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning and other legal matters.
8When Morgan Stanley Smith Barney LLC, its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors (collectively, “Morgan Stanley”) provide “investment advice” regarding a retirement or welfare benefit plan account, an individual retirement account or a Coverdell education savings account (“Retirement Account”), Morgan Stanley is a “fiduciary” as those terms are defined under the Employee Retirement Income Security Act of 1974, as amended (“ERISA”), and/or the Internal Revenue Code of 1986 (the “Code”), as applicable. When Morgan Stanley provides investment education, takes orders on an unsolicited basis or otherwise does not provide “investment advice”, Morgan Stanley will not be considered a “fiduciary” under ERISA and/or the Code. For more information regarding Morgan Stanley’s role with respect to a Retirement Account, please visit www.morganstanley.com/disclosures/dol. Tax laws are complex and subject to change. Morgan Stanley does not provide tax or legal advice. Individuals are encouraged to consult their tax and legal advisors (a) before establishing a Retirement Account, and (b) regarding any potential tax, ERISA and related consequences of any investments or other transactions made with respect to a Retirement Account. Individuals should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
9Insurance products are offered in conjunction with Morgan Stanley Smith Barney LLC’s licensed insurance agency affiliates.
10Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
11Annuities are offered in conjunction with Morgan Stanley Smith Barney LLC’s licensed insurance agency affiliates.
Check the background of our Firm and Investment Professionals on FINRA's BrokerCheck*.
The information, products and services described here are intended only for individuals residing in states where this Financial Advisor is properly registered as described in this site.
Morgan Stanley reserves the right, to the extent permitted under applicable law, to retain and monitor all electronic communications. Morgan Stanley will not accept purchase or sale orders via any Internet site, social media site and/or its messaging systems. Morgan Stanley does not endorse and is not responsible and assumes no liability for content, products or services posted by third-parties on any Internet site, social media site and/or its messaging systems. All electronic communications are subject to terms available at the following link:
https://www.morganstanley.com/disclaimers/mswm-email.html. Any profiles and associated content are for U.S. residents only.
The securities/instruments, services, investments and investment strategies discussed in this material may not be appropriate for all investors. The appropriateness of a particular investment, investment strategy or service will depend on an investor's individual circumstances and objectives. Morgan Stanley Smith Barney LLC recommends that investors independently evaluate particular investments, strategies and services, and encourages investors to seek the advice of a Financial Advisor or Private Wealth Advisor. This material does not provide individually tailored investment advice. It has been prepared without regard to the individual financial circumstances and objectives of persons who receive it.
Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors or Private Wealth Advisors do not provide tax or legal advice. Individuals should consult their tax advisor for matters involving taxation and tax planning and their attorney for legal matters.
Morgan Stanley Smith Barney LLC (“Morgan Stanley”) is not implying an affiliation, sponsorship, endorsement with/of the third party or that any monitoring is being done by Morgan Stanley of any information contained within the website. Morgan Stanley is not responsible for the information contained on the third-party website or the use of or inability to use such site. Nor do we guarantee their accuracy or completeness.
The views, opinions or advice contained within third party websites or materials are solely those of the author, who is not a Morgan Stanley employee, and do not necessarily reflect those of Morgan Stanley Smith Barney LLC, or its affiliates. The strategies and/or investments referenced may not be appropriate for all investors as the appropriateness of a particular investment or strategy will depend on an investor's individual circumstances and objectives.
*References to length of service at Morgan Stanley include years at Morgan Stanley and predecessor firms.
Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization's initial and ongoing certification requirements to use the certification marks.
The use of the CDFA designation does not permit the rendering of legal advice by Morgan Stanley or its Financial Advisors which may only be done by a licensed attorney. The CDFA designation is not intended to imply that either Morgan Stanley or its Financial Advisors are acting as experts in this field.
Awards Disclosures | Morgan Stanley
CRC 4665150 (8/2025)
