Photo of Malaika K. Caldwell

Malaika K. Caldwell

Senior Counsel




University of Illinois Chicago School of Law, J.D., 2011; LL.M., 2012

Elmhurst College, B.S., 2007

Bar Admissions

Malaika Caldwell's practice centers around the design and implementation of employee benefits and executive compensation arrangements. Malaika advises employers, fiduciaries, plan sponsors and trustees on employee benefit matters intersecting with ERISA, IRC, COBRA, FMLA and HIPAA. She provides advice on a wide range of retirement plan design, governance and administration issues.

Malaika also advises employers on health and welfare benefit issues, including working with employers to design welfare benefit offerings, drafting cafeteria plan documents, wrap plan documents summary plan descriptions, and enrollment materials and notices. Her experience includes Section 125 cafeteria plans, medical savings accounts (such as flexible spending arrangements (FSAs), health reimbursement arrangements (HRAs) and health savings accounts (HSAs), wellness programs and Affordable Care Act (ACA) compliance strategies. She also represents health plans, medical providers and business associates on HIPAA compliance issues.

Malaika advises clients on issues related to the design, compliance and administration of defined benefit plans and all forms of defined contribution plans (including profit sharing, 401(k), 403(b) and 457 plans). Her practice includes drafting plan documents and amendments, preparing ERISA disclosures, preparing and submitting Internal Revenue Service determination letters, extensive experience under the EPCRS correction program submissions, reviewing qualified domestic relations orders (QDROs), and negotiating third party administrator and service agreements.

Malaika also has extensive experience with benefit issues associated with corporate transactions, including plan terminations, change of control parachute excise taxes, mergers and acquisitions, and other corporate matters. She also counsels clients on complex taxation issues associated with IRC §409A and §280G.

Malaika has considerable experience in governmental compliance programs with the Internal Revenue Services and Department of Labor compliance divisions, having served as an Investigator with the DOL's Employee Benefit Security Administration. Additionally, Malaika provides advice and due diligence review on mergers and acquisitions, state minimum wage, overtime laws and state-by-state COVID-19 employer requirements.


Illinois Super Lawyers Rising Star, 2019 and 2020

Professional Activities

Chicago Bar Association

Black Women Lawyers' Association

Civic, Cultural & Social Activities

BUILD, Inc., Board of Directors