1. Raymond J. Lester, CLU, FLMI
1964 South Sparrow Court
Libertyville IL 60048
847-217-3910 ray.lester@comcast.net
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Summary
I am an insurance attorney with extensive experience in the United States and London in all aspects
of reinsurance and insurance law and regulatory matters. Lean Six Sigma Green Belt. Certified Project
Manger. Proficient in Microsoft Office software.
Experience
Attorney at Law March 2013-Present
Private practice of law. Litigation consultant for managed care litigation. Private Party and Court
appointed arbitrator. Consultant to the Illinois Department of Insurance.
Trustmark Insurance Company, Lake Forest 1986 – September 2012
Vice President and Associate General Counsel
Represented the company in its major mergers and acquisitions:
· Negotiated and documented a sports program which required each team to insure the multi-million
dollar salaries of the six highest paid players in the National Basketball Association and the National
Hockey League and the international reinsurance placements supporting the program.
· Negotiated and closed the purchase of a life insurer operating under the supervision of Minnesota
Department of Insurance and subsequent merger of the company into Trustmark Life Insurance
Company. Several years later obtained regulatory approval for and implemented the re-
domestication of Trustmark Life from Minnesota to Illinois.
· Negotiated the acquisition of Bankers Life Insurance Company and its blocks of life Insurance and
annuity business. Subsequently handled the transfer of the annuity block to National Guardian Life
when the decision was made to exit the annuity business.
· Negotiated and closed the purchase of a large block of group universal life insurance and the related
marketing organization from Alexander Hamilton Life.
· Negotiated and closed the acquisitions of:
▪ CoreSource, the then largest third party health claim administrator in the country with offices
in 6 states and over 1,000 employees.
▪ The Hartford’s entire block of non-cancelable individual disability insurance with over $130
million in reserves transferred to the company.
▪ The entire group health insurance operations of Reliastar along with the related offices in
three states and over 400 employees.
· Lobbied for passage of the Illinois Mutual Holding Company Act and implemented the conversion
and reorganization of Trustmark to a mutual holding company structure.
· Compliance Officer. Oversaw market conduct examinations performed on the company by the
various state insurance departments.
· Managed the defense of a multi-million dollar class action lawsuit resulting in the denial of class
certification and a favorable jury verdict.

2. Raymond J. Lester Page 2
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· Successfully managed the defense of a string of high profile and emotionally charged experimental
treatment claim denials across the nation resulting in a favorable decision in each case.
· Handled employment issues including representing the company in actions brought by the Illinois
Department of Human Rights and the EEOC. Managed employment related litigation against the
company.
· Responsible for the company’s Intellectual Property portfolio.
· Responsible for renewing corporate charters for the various subsidiaries and the filing of required
reports.
Led a team responsible for facultative and treaty reinsurance litigations and arbitrations involving issues
of contract interpretation, allocation, rescission and fronting in disputes pending in the United States,
the United Kingdom, Canada and Bermuda. Personally supervised the largest litigation exposures to
the company, including bad faith / extra-contractual obligation jury trials, class actions and reinsurance
litigations / arbitrations. Managed:
· Litigation brought against the company by an AIG subsidiary seeking in excess of $300 million in
damages concerning the reinsurance of a large block of California Workers Compensation claims.
The filing of this lawsuit resulted in a downgrade of the company’s AM Best rating. Delivered result:
Case successfullysettled for a confidential amount on the eve of trial. The settlement of this litigation
resulted in a restoration of the company’s AM Best “A” rating.
· An arbitration brought by the company against AIG seeking $17.5 million in damages for breach of
contract concerning the reinsurance of certain property and casualty risks in the London Market.
Delivered result: an award of $17.5 million, the full amount claimed due.
· A litigation brought by two large multinational property and casualty insurers seeking $180 million in
damages against the company under a reinsurance program covering a large block of workers
compensation claims. Delivered result: I successfully negotiated a tripartite settlement reducing the
company’s liability to $65 million.
· Litigation against the largest health insurer in the country seeking $8.2 million in damages for the
improper reporting of medical claim payments. Delivered result: Case successfully settled without
the need for a costly trial in September 2012 for $6.5 million.
· An arbitration against a Bermuda reinsurer seeking $36 million in claims due under a reinsurance
contract. Case settled prior to hearing for $32 million.
· An arbitration brought by the company seeking $36 million in damages from a Lloyds syndicate for
failing to pay reinsured workers compensation claims. Delivered result: A $40 million award, more
than the amount claimed, in favor of the company against the Syndicate.
· Successfully handled other complex multimillion dollar reinsurance litigations spanning the United
States and the United Kingdom.
· Implemented e-billing software that reduced company’s legal spend by 15%.
Private Practice of Law, Homewood, IL 1984 – 1986
General Practice with a focus on Bankruptcy and Family matters, including contested custody cases

3. Raymond J. Lester Page 3
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Interlake Steel, Riverdale, IL 1978 – 1984
Credit and Collections Analyst
Analyzed financial statements established credit lines for industrial customers andcollected receivables
in a timely manner. Was responsible with others for managing and collecting the company’s largest
asset, its accounts receivables portfolio. Reviewed bankruptcy filings of defunct accounts and advised
management of the related financial implications.
Education
Executive Development Program, Kellogg Graduate School of Management, Evanston, IL
Juris Doctor with High Distinction John Marshall Law School, Chicago, IL
B.S. Finance (Dean’s List), University of Illinois, Urbana IL
Bar Admissions
Illinois 1984
US District Court, Northern District 1984
US Supreme Court 1987
Affiliations
Fellow, Life Management Institute
Chartered Life Underwriter
Member, Association of Life Counsel
Board Member of the Illinois Life and Health Guaranty Fund 1990-2012
Member, University of Illinois Math Advisory Board 2015-2018
Arbitrator for the Circuit Court of Lake County, Illinois
ARIAS US Certified arbitrator 2003-2011
Illinois Licensed P & C Broker 1975-1995
Certified Project Manager (PMP)
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