Jorge Leon Photo

Jorge M. Leon

Group Co-Leader, Employee Benefits
Co-Chair, Diversity, Equity & Inclusion Committee


Jorge is at the forefront of advising on emerging fiduciary issues related to ERISA cybersecurity and litigation mitigation. Clients have entrusted Jorge and his team to oversee the design and administration of their health and welfare programs, executive compensation arrangements, and retirement plans. As a boardroom insider for public and privately-held companies, Jorge enjoys the confidence of directors, compensation committees and C-suite executives and helps them solve critical compensation and benefit issues.

Plan sponsors, administrators, fiduciaries, insurers and third-party recordkeepers turn to Jorge for strategic counsel on designing, establishing, and maintaining benefit and compensation plans. Clients laud his responsiveness and meticulous approach to matters ranging from plan establishment and design to government investigations and inquiries, ongoing compliance and qualification, ERISA litigation, and mergers and acquisitions.

Before joining Michael Best, Jorge practiced for 15 years at a premiere Chicago-based AmLaw 100 firm, where he was the lead partner for qualified plan matters. He brings a strong record of successful outcomes, an uncompromising level of service, and improved cost efficiency to his current practice.

As a leading ERISA practitioner and thought-leader on diversity, Jorge’s opinions and views are frequently sought by nationally recognized publishers, journalists, bar associations and professional organizations. Jorge has also advised regulators and legislators on various policies impacting benefits. As an example of the impact Jorge has on national policy, his views on the CARES Act that were published by Law360 have been affirmed by the IRS in Notice 2020-50.

As a general problem-solver and external general counsel in higher education, Jorge has helped clients with their non-benefit needs. These clients have ranged from colleges and publicly-traded and privately-held companies to ultra-high-net-worth individuals in the NFL and financial world.  Recent matters Jorge has successfully handled for these clients involved M&A, banking regulatory compliance, corporate/commercial law, real estate, immigration, employment law, bankruptcy, debt restructuring, turnarounds, and various types of litigation (e.g., commercial, cybersecurity, securities and employment).

Deep knowledge, broad experience

Jorge is well versed in the intricacies of 401(k), 403(b), 457(b), and defined benefit plans. Within the benefit and compensation arena, his practice includes:

  • Providing ERISA subject matter expertise and defense strategies in one of the first ERISA cybersecurity litigations that resulted in landmark rulings
  • Negotiating ERISA 3(21) and 3(38) investment advisor/manager agreements, as well as the benefit aspects of sizable corporate transactions
  • Counseling clients on the administrative, design, legal, and testing considerations of recordkeeping conversions
  • Negotiating third-party recordkeeping agreements relating to plans holding between $1 million to $5 billion in assets
  • Supervising the transition of insurers/claims administrators for health and welfare plans
  • Restructuring health and welfare plans to achieve cost efficiencies and legal compliance
  • Resolving various audit, administrative, and compliance issues involving qualification, fiduciary, and reporting issues with the Internal Revenue Service (IRS), the Department of Labor (DOL), and the Pension Benefit Guaranty Corporation (PBGC)
  • Designing fiduciary policies and internal controls for plan sponsors, fiduciaries, and administrators
  • Employee Plans Compliance Resolution System (EPCRS), Voluntary Fiduciary Correction Program (VFCP), and prohibited transactions
  • Counseling clients on design options for safe harbor plans, including 401(k)(12) and Qualified Automatic Contribution Arrangements (QACA)
  • Advising employer-trustees in establishing and maintaining Taft-Hartley plans
  • Advising public, privately-held and higher education clients on various qualification, correction, and administrative issues and plan communication strategies
  • Advising hedge fund and venture capital clients on the ERISA plan asset rules and on state open disclosure requirements


Proactively counseling to avoid litigation

During the 2020 wave of ERISA fee litigation, administrative and investment committees and related fiduciaries have actively sought out Jorge’s counsel in light of his work and experience during the first wave of fee litigation that started in 2006 and the 2016 wave that impacted the higher education industry. Specifically, Jorge has addressed how to establish committees, the applicable governance and standards of conduct and best practices to minimize the risk of being sued.

Guiding executive relations

When sensitive benefit and compensation issues arise for executives and members of the leadership team, Jorge has been called upon by boards and compensation committees to navigate and balance expectations, non-discrimination rules and relations between leadership and staff. This has encompassed one-on-one counseling and messaging and the development of legally-compliant creative corrections and third-party financial arrangements.

Advising a major municipality

Jorge counseled the largest municipal employer in Illinois on the design and fiduciary aspects of its 457(b) plan, with over $4 billion in assets.

Breaking new ground in ERISA issues

When a then-unknown plaintiff law firm targeted numerous large employers and plans with class actions claiming excessive fees and mismanagement of 401(k) plans, Jorge provided subject matter advice to both a client and their litigation team on this seminal ERISA action, resulting in the parties reaching a mutually agreeable settlement. Ultimately, Jorge’s work contributed to the development of the groundbreaking fee disclosure rules under ERISA. Most recently, Jorge was part of the litigation defense teams on ERISA cybersecurity, excess fee and TDF litigations that led to landmark shifts in fiduciary liability standards.

Taking on the IRS

Jorge mounted a successful defense of a client’s safe harbor 401(k) plan with approximately $4 billion in assets and more than 30,000 participants during an IRS audit that resulted in no penalties being assessed. He also represented a client before the IRS on complicated leased employee and related nondiscrimination testing issues where there was no existing regulatory guidance, helping to influence the development of new leased employee policies as a result.

Advocating for changes to COBRA/State Spousal Continuation Coverage

Jorge’s counsel in regard to a large health insurer’s spousal health continuation obligations led to a change in systems and procedures on a statewide basis, benefiting thousands of spouses who were entitled to health coverage after their partners terminated employment.

Other notable representations include:

  • Successfully defended a client’s 403(b) plan during a DOL audit, which resulted in the assessment of minimal penalties
  • Converted recordkeepers for defined contribution plans holding approximately $8 billion in assets
  • Represented clients during PBGC investigations relating to reportable events, resulting in the successful close of acquisitions and changes in controlled groups
  • Assessed the merits of settlement strategies for various alleged ERISA fiduciary breach lawsuits
  • Handled benefit aspects of the $200 million sale of an IT service provider
  • Handled benefit aspects of a purchaser’s $825 million acquisition of an information systems group
  • Handled benefit aspects of multimillion-dollar acquisitions and divestitures of various manufacturing clients  

Focus on Diversity & Inclusion

Jorge is deeply committed to diversity and inclusion and has been actively at the forefront on diversity since his time in law school. He helped found the diversity committee at his prior firm at a time when such committees were considered a novelty. Jorge brought his passion and expertise on diversity and inclusion to Michael Best and its Diversity, Equity & Inclusion Committee. Jorge has helped develop policies and programs aimed at recruiting and retaining racially, gender and LGBTQ diverse talent at all levels. These efforts help over 500 workers firm-wide feel safe and secure in their jobs. Additionally, he has spearheaded firm-wide initiatives that promote social justice, civic engagement and access to educational, health, nutrition and government resources within predominantly minority communities. Clients, publishers and professional organizations frequently seek Jorge’s views and counsel as a thought-leader on diversity and inclusion. Examples of his accomplishments include:

  • Increased the firm’s HRC Corporate Equality Index rating from 15% to 100%
  • Successfully coordinate and prepare survey, client inquiries and award submissions on diversity
  • Founded the firm’s ERG for racially and LGBTQ diverse lawyers and engineers
  • Collaborated to create diverse law student scholarship program
  • Developed nationwide diversity service day program
  • Developed mentoring programs for diverse lawyers, law students and engineers within the firm and in the community
  • Collaborated to develop transgender, charitable giving and enhanced parental leave policies
  • Serve in leadership roles with organizations focused on LGBTQ and racial diversity
  • Interviewed by various HR and diversity publications

Honors & Recognitions

  • Notable Leader in Employment & Labor Law, Crain’s Chicago Business, 2023
  • Top 10 Influential Illinois Lawyers Shaping Employee Benefits & Executive Compensation, Business Today News, 2023
  • Notable Gen X Leaders in Accounting, Consulting and Law, Crain's Chicago Business, 2021-Present
  • Notable Nonprofit Board Leader, Crain's Chicago Business, 2022
  • Notable LGBTQ Executives, Crain’s Chicago Business, 2020, 2021
  • Chicago’s Most Notable Minority Lawyers, Crain’s Chicago Business, 2018, 2019, 2020
  • Nation's Best List, Lawyers of Color, 2019
  • Included in Who’s Who in Hispanic Chicago, Negocios Now, 2018-2020
  • Leading Employee Benefits & Compensation Lawyer, Chambers USA, 2019-Present
  • Recognized Practitioner, Employee Benefits & Compensation, Chambers USA, 2016, 2017, 2018
  • “Illinois Super Lawyers” list in the area of Employee Benefits, Super Lawyers magazine, 2018-Present
  • Most Influential Minority Lawyers in Chicago, Crain's Custom Media, 2017
  • Top Latino Lawyers, Latino Leaders magazine, 2016-2020
  • Law360 Rainmaker, 2016

Professional Activities

  • Host Committee Member, National Black Pre-Law Conference and Law Fair, 2022
  • Fellow, Leadership Council on Legal Diversity, 2018
  • Fellow, The Fellows of the American Bar Foundation, 2018-Present
  • Board Member, Hispanic Lawyers Association of Illinois Charities, 2018-Present
  • Chair and Co-chair, Michael Best Diversity, Equity & Inclusion Committee, 2014-Present
  • Member, Leadership Advisory Council of the Wisconsin LGBT Chamber of Commerce, 2017-Present
  • Advisor on Employee Benefits, Program Committee of the Board of Directors, American Law Institute Continuing Legal Education, 2008-2016
  • Financial Director, Zeta Corporation, 1998-2011

Bar Associations

  • Member, American Bar Association
  • Member, Asian American Bar Association
  • Member, Hispanic National Bar Association
  • Member, Hispanic Lawyers Association of Illinois
  • Member, Lesbian and Gay Bar Association of Chicago


Bar Admission

Court Admission


Community Involvement

  • Member, Economic Club of Chicago, 2015-Present
  • Board of Directors, Gads Hill Center, 2015-Present
  • Board of Trustees, Field Museum, 2020-Present
  • Board of Trustees, Northeastern Illinois University, 2023-Present



Bar Admission

Court Admission


Community Involvement

  • Member, Economic Club of Chicago, 2015-Present
  • Board of Directors, Gads Hill Center, 2015-Present
  • Board of Trustees, Field Museum, 2020-Present
  • Board of Trustees, Northeastern Illinois University, 2023-Present
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