Jorge M. Leon

Jorge is a trusted advisor to boards, executives, and fiduciaries confronting complex, high-stakes legal and business challenges. He is frequently engaged when issues are novel, sensitive, or consequential—particularly where compensation, benefits, governance, regulatory risk, and enterprise strategy intersect.

At the forefront of emerging fiduciary issues, including ERISA cybersecurity and litigation risk mitigation, Jorge has been entrusted with the design, oversight, and defense of health and welfare programs, executive compensation arrangements, and retirement plans for public, private, and nonprofit organizations. As a boardroom insider, he enjoys the confidence of directors, compensation committees, and C-suite leaders and is valued for his judgment, clarity, and ability to translate complexity into actionable solutions.

Clients rely on Jorge not only for technical excellence, but for his ability to anticipate risk, navigate ambiguity, and solve problems before they escalate—whether the matter involves regulatory scrutiny, litigation exposure, governance challenges, or transformational business activity.

Plan sponsors, administrators, fiduciaries, insurers, and third-party service providers turn to Jorge for strategic counsel across the full lifecycle of benefit and compensation arrangements—from initial design and governance to crisis response, investigations, litigation, and transactions. Clients consistently cite his responsiveness, meticulous approach, and practical guidance on matters ranging from government audits and ERISA litigation to mergers, acquisitions, and corporate restructuring.

Before joining Michael Best, Jorge practiced for 15 years at a premier Chicago-based AmLaw 100 firm, where he served as lead partner on qualified plan matters. He brings to his current practice a record of successful outcomes, disciplined risk management, and a client-centric approach that improves efficiency without compromising quality.

As a leading ERISA practitioner and thought-leader, Jorge’s opinions and views are frequently sought by nationally recognized publishers, journalists, bar associations and professional organizations. Jorge has advised regulators and legislators on various policies impacting benefits. Some of Jorge’s views on benefits and related policy have been affirmed by the DOL and IRS in published guidance.

As a general problem solver and external general counsel—particularly within higher education—Jorge regularly assists clients beyond traditional benefits matters. He is often called when organizations need a steady hand to assess risk, coordinate across disciplines, and drive solutions efficiently. These engagements have included advising colleges, publicly traded and privately held companies, and ultra-high-net-worth individuals in industries ranging from finance to professional sports. Recent matters have spanned mergers and acquisitions, banking and regulatory compliance, corporate and commercial law, real estate, environmental issues, immigration, employment law, bankruptcy, debt restructuring, operational turnarounds, and complex litigation, including cybersecurity, securities, and employment disputes.

Deep technical experience

Jorge combines deep technical command with a broad understanding of how benefit and compensation decisions affect governance, culture, financial performance, and litigation risk. He is well versed in the intricacies of 401(k), 403(b), 457(b), and defined benefit plans, and regularly advises clients on:

• Serving as ERISA subject-matter counsel and defense strategist in one of the first ERISA cybersecurity litigations, resulting in landmark rulings
• Advising on and negotiating ERISA §3(21) and §3(38) investment advisor and manager agreements
• Counseling on recordkeeping conversions, including administrative, design, legal, and testing considerations
• Negotiating third-party recordkeeping and service provider agreements for plans holding between $1 million and $5 billion in assets
• Leading insurer and claims administrator transitions for health and welfare plans
• Restructuring health and welfare plans to improve cost efficiency while maintaining compliance
• Resolving IRS, DOL, and PBGC audits and investigations involving qualification, fiduciary, reporting, and prohibited transaction issues
• Designing fiduciary governance frameworks, policies, and internal controls for plan sponsors, fiduciaries, and administrators
• Guiding clients through EPCRS, VFCP, and other correction and voluntary compliance programs
• Advising on safe harbor and automatic enrollment plan designs, including 401(k)(12) and QACA structures
• Counseling employer-trustees on the establishment and administration of Taft-Hartley plans
• Advising public, private, and higher education clients on qualification, correction, administration, and participant communications
• Counseling hedge fund and venture capital clients on ERISA plan asset rules and state disclosure requirements