Mary Claire Chesshire

Partner
blank image Mary Claire Chesshire

Mary Claire Chesshire

Partner
Towson T: 410.347.9465 F: 410.234.2309
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Mary Claire Chesshire

Mary Claire Chesshire

PARTNER
mchesshire@whitefordlaw.com
TOWSON
T: 410.347.9465
F: 410.234.2309
Biography
BIOGRAPHY

Ms. Chesshire advises for-profit, nonprofit and governmental entities in all aspects of employee benefits law.  Clients served range from sole proprietorships to state governments, and include clients in both established and start up and emerging  businesses.  Ms. Chesshire’s experience includes more than thirty years of service to clients in the employee benefits industry.

Recognitions

  • Chambers USA, Maryland, Employee Benefits & Executive Compensation (2006–Present)
  • The Best Lawyers in America®, Baltimore Employee Benefits (ERISA) Law (2025), Employee Benefits (ERISA) Law  "Lawyer of the Year" (2023), Nonprofit/Charities Law (2007–Present); Nonprofit/Charities Law - Baltimore "Lawyer of the Year" (2017)
  • Maryland Super Lawyers®, Employee Benefits (2007–2020)
  • Baltimore SmartCEO Magazine, "Baltimore's Legal Elite" (2010)
  • Baltimore Magazine, "Top Lawyer: The Next Generation" (April 2003)
 

Memberships & Activities

Bar & Professional Associations

  • Member:  Maryland State Bar Association
  • Member:  Bar Association of Baltimore City
  • Member:  National Association of Public Pension Attorneys (1993 - 2016)


Boards & Community Service

  • Member: Board of Trustees and Executive Committee, Stevenson University (2003-2015)
  • Member and Secretary: Baltimore Chapter, EWGA (formerly, Executive Women’s Golf Association) (2000 – 2002)
  • Graduate: Greater Baltimore Committee Leadership Program (2007)
  • Chambers and Partners Designation

Employee Benefits/ERISA

  • Tax-qualified retirement plan design and advice - for profit, not-for-profit and state and local government employers
  • Review of third party administrator prototype retirement plan documents
  • Preparation and review of employee communications pertaining to retirement and welfare benefit plans 
  • Advice to parties in merger, acquisition and other business transactions regarding employee benefit plan issues
  • Welfare benefit plan design, advice and drafting
  • Preparation and review of qualified domestic relations orders
  • Analysis of potential prohibited transaction issues involving retirement and welfare benefit plan assets 
  • Preparation of trust documents to fund other post-employment benefits for local governments
  • Negotiation of service agreements with third party administrators
 

Health Care Plans

  • Federal and state COBRA compliance pertaining to continuation of employer-provided health care benefits
  • Welfare benefit plan design, advice and drafting
 

ERISA Compliance

  • Advice to retirement and welfare plan sponsors in all aspects of ERISA compliance
  • Representation of retirement plan sponsors in connection with Internal Revenue Service and Department of Labor audits
  • Representation of retirement plan sponsors in connection with Internal Revenue Service and Department of Labor correction programs
  • Successful negotiation of agency penalty reductions 
  • Interaction with outside auditors of retirement plan financial statements
 

Executive Compensation

  • Design and drafting of nonqualified deferred compensation plans
  • Section 409A compliance
 

Nonprofit Organizations and Associations

  • Tax-qualified retirement plan design and advice
  • Section 403(b) and 457 plan design and drafting
  • Compensation and benefit analysis for avoidance of intermediate sanctions
 

Employment Issues in Higher Education

  • Retirement, welfare and deferred compensation planning and advice
  • Compensation and benefit analysis for avoidance of intermediate sanctions
 

Business & Corporate Law

  • Advice to parties in merger, acquisition and other business transactions regarding employee benefit plan issues
INSIGHTS

Speaker: "Trends in Employee Compensation and Benefits," Ask Us Anything Webinar (2022)

Author: "Retirement Plan Update: What Clients Are Seeing and What is Coming" Maryland State Bar Association Labor & Employment Law Newsletter (2022)

Co-Author:  "Employees are Requesting Shariah Compliant Investment Options - What Now?" Maryland State Bar Association Labor & Employment Law Newsletter (2022)

Presenter:  2013 Maryland Association of Certified Public Accountants Government and Nonprofit Conference

Presenter:  Whiteford, Taylor & Preston Employment Law Update

Presenter:  Maryland Government Finance Officers Association Summer Meeting

Lecturer:  Stevenson University Paralegal Program (1995-1998)

Volunteer Trainer: Maryland Association of Nonprofit Organizations

ARTICLES

October 24, 2022

State Mandated Retirement Programs

Maryland’s mandated retirement plan is up and running.  Virginia’s and Delaware’s plans are not far behind. 
 
The State of Maryland now requires all private employers, with few exceptions, to provide a retirement savings vehicle for employees.  The MarylandSaves program is now active and employers that have at least one W-2 employee can expect to receive notices alerting them to sign up or obtain an exemption.
 
Delaware is expected to roll out its mandated retirement program in 2025 and Virginia is expected to do so in 2023. 
December 13, 2021

Retirement Plan Update: What Plan Sponsors Are Seeing and What is Coming

If your association or organization sponsors one or more retirement plans, you should be on the lookout for outreach from your recordkeepers or plan document providers.  Please note that many times the outreach comes through the providers’ employer portal with a corresponding email to the contact of record.  You should verify that the designated contact person is correct.  Failure to adopt the amendments described below in a timely manner may result in assessment of penalties by the Internal Revenue Service or disqualification of the retirement plans.
March 22, 2021

Women's History Month - Organizations We Support

In celebration of Women's History Month and the contributions and dedication of our female attorneys, we are spotlighting nonprofits and organizations we have sponsored, been involved with and supported throughout the past year.
February 27, 2018

Your Fiduciary Duty: Find Missing Retirement Plan Participants

Does your association have more retirement plan participants than it does full-time staff? If so, you have a fiduciary duty to find former employees who are owed benefits—and the Department of Labor is paying increased attention to who is meeting it.

October 30, 2017

The Frequently Neglected 403(B) Plan - Errors May Be Costly

We previously discussed the differences between deferred compensation plans for tax-exempt employers, in particular; the tax attributes of Internal Revenue code Section 457(b) and 457(f) plans. However; participation in 457(b) and 457(f) programs is limited to a "select group of management or other highly compensated employees" and those arrangements generally serve as a supplement to the retirement programs available for all employees.
September 2, 2015

Mind Your B's and F's: A Primer on Deferred Compensation Plans for Tax Exempts

Retirement programs for employees of tax exempt associations are similar in many ways to retirement programs sponsored by a for-profit business enterprise.  Both types of organizations may offer generally all of their employees qualified retirement plans (401(k) plans for both, 403(b) plans only for tax exempts) and deferred compensation plans for a “select group of management or other highly compensated employees.”  However, the tax treatment of deferred compensation arrangements is where the similarities between tax exempt and for-profit organizations end.  

March 23, 2015

How Simple is that Simple Retirement Plan, Really?

Small employers with less than 100 employees may opt to install a “SIMPLE” IRA Plan or a Simplified Employee Pension Plan (SEP) as an alternative to a traditional qualified retirement plan such as a profit sharing plan or 401(k) plan.  The benefits of the arrangements are meaningful – there is no required discrimination testing, no annual reporting, and no lengthy plan document required to be adopted, but, by establishing such a plan, a small employer can provide a meaningful retirement benefit to employees and a business owner can shelter income from current taxes. 

January 30, 2014

I Got This Thing From the IRS.......

The Internal Revenue Service is now launching questionnaire projects to gather information about retirement plans, in addition to conducting random, full scope audits.  What should you do if a questionnaire is received?  First - do not ignore it and, second, ask your advisor to help with the responses.  A proactive review of your retirement plans’ operations is never a bad idea. 

May 3, 2012

Retirement Plan Disclosure Deadline Looms

Nonprofit organizations and associations may be feeling a little more loved by the custodians of their retirement plan assets and third party administrators lately, if “love” means how many communications you’re getting about the upcoming deadline for fee and investment disclosures. 

July 22, 2010

COBRA Health Continuation Coverage Subsidy Extension

On February 17, 2009, President Obama signed the American Recovery and Reinvestment Act of 2009, referred to in the press as the Economic Stimulus Act. One provision in this Act that had an immediate impact on employers who provide health benefits to employees was a 65% subsidy for former employees and their dependents who have elected, or were offered the opportunity to elect, to continue health insurance coverage following involuntary termination of employment.

August 3, 2009

Economic Stimulus Act - Impact on COBRA Health Continuation Coverage

On February 17, 2009, President Obama signed the American Recovery and Reinvestment Act of 2009, referred to in the press as the "Economic Stimulus Act."  One provision in this Act that has received relatively little publicity is a subsidy for former employees and their dependents who elected, or were offered the opportunity to elect, to continue health insurance coverage following termination of employment.
October 27, 2004

Required Changes to Non-Qualified Deferred Compensation Plans

On October 22, 2004, President Bush signed into law the American Jobs Creation Act of 2004. This legislation adds new Section 409A to the Internal Revenue Code. Section 409A will require most employers to amend their non qualified deferred compensation plans (“NQDCPs”) and to operate the plans under new rules imposed by Section 409A.

NEWSLETTERS

December 14, 2021

Associations, Nonprofits and Political Organizations Report - Fall 2021

Update Concerning Meetings and Related Issues in Light of COVID Variants and the Anime Convention

Retirement Plan Update: What Plan Sponsors Are Seeing and What is Coming

ESG Investing – Was Sort of Allowed, Was Disallowed, Now Allowed Again?

Meet the Team: Attorney Spotlight on Eileen Morgan Johnson
August 17, 2023 - Honors & Awards

A Record 87 Whiteford Attorneys Listed in Best Lawyers in America 2024, Ten Selected as “Ones to Watch”

87 lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2024 (copyright 2023 by Woodward/White, Inc., of Aiken S.C.). New practice areas of recognition include CleanTech Law and Entertainment and Sports Law. The lawyers selected are based in the firm’s Delaware, Maryland, Pennsylvania, Virginia and Washington offices. Client comments are posted on the Best Lawyers website, at bestlawfirms.com.
June 1, 2023 - Honors & Awards

Chambers Honors Whiteford in 14 Practice Areas

Whiteford is pleased to announce that Chambers and Partners has once again ranked the firm highly in its 2023 list of leading firms and business lawyers.
August 18, 2022 - Honors & Awards

73 Whiteford Attorneys Listed in Best Lawyers in America 2023, Six Selected as “Lawyer of the Year”

73 lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2023 (copyright 2022 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Delaware, Maryland, Pennsylvania, Virginia and Washington, D.C. offices. Client comments are posted on the U.S. News & Best Lawyers web site, at bestlawfirms.com.
June 1, 2022 - Honors & Awards

Chambers Honors Whiteford in 14 Practice Areas

Whiteford, Taylor & Preston is pleased to announce that Chambers and Partners has once again ranked the firm highly in its 2022 list of leading firms and business lawyers. This year’s recognition includes 29 attorneys in 14 practice areas at the National and State level.
August 19, 2021 - Honors & Awards

75 Whiteford Attorneys Listed in Best Lawyers in America 2022, Eight Named “Ones to Watch”

A record 75 lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2022 (copyright 2021 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Delaware, Maryland, Pennsylvania, Virginia and Washington offices. Client comments are posted on the U.S. News & Best Lawyers web site, at bestlawfirms.com.
April 23, 2021 - Honors & Awards

Chambers Honors Whiteford in 11 Practice Areas

Whiteford, Taylor & Preston is pleased to announce that Chambers and Partners has once again ranked the firm highly in its 2021 list of leading firms and business lawyers. This year’s recognition includes 25 attorneys in 11 practice areas in 3 states and the District of Columbia.
August 20, 2020 - Honors & Awards

71 Whiteford Attorneys Listed in Best Lawyers in America 2021, Six Named “Lawyer of the Year”

A record 71 lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2021 (copyright 2020 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Delaware, Maryland, Pennsylvania, Virginia and Washington offices. Client comments are posted on the U.S. News & Best Lawyers web site, at bestlawfirms.com.
April 22, 2020 - Honors & Awards

Chambers Honors Whiteford in 10 Practice Areas

Whiteford, Taylor & Preston is pleased to announce that Chambers and Partners has once again ranked the firm highly in its 2020 list of leading firms and business lawyers. This year’s recognition includes 23 attorneys in 10 practice areas in 3 states and the District of Columbia.
August 15, 2018 - Honors & Awards

57 WTP Attorneys Listed in Best Lawyers in America 2019, Four Named "Lawyer of the Year"

57 lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2019 (copyright 2018 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Delaware, Maryland, Virginia and Washington offices. Client comments are posted on the U.S. News & Best Lawyers web site.
August 15, 2017 - Honors & Awards

59 WTP Attorneys Listed in Best Lawyers in America 2018, Two Named "Lawyer of the Year"

59 lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2018 (copyright 2017 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Maryland, Washington and Virginia offices. Client comments are posted on the U.S. News & Best Lawyers web site, at bestlawfirms.com.

In addition, two lawyers were selected as “Lawyer of the Year” for their particular areas of practice.

May 30, 2017 - Honors & Awards

Whiteford, Taylor & Preston and 29 Lawyers Honored by Chambers and Partners

Whiteford, Taylor & Preston is pleased to announce that Chambers and Partners has once again ranked the firm highly in its 2017 list of leading firms and business lawyers. This year’s recognition includes a record 29 attorneys in 4 states, the District of Columbia and Afghanistan. 

August 15, 2016 - Honors & Awards

59 Whiteford, Taylor & Preston Attorneys Listed in Best Lawyers in America, 2017, Eight Named as "Lawyers of the Year"

Fifty-nine lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2017 (copyright 2016 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Maryland, Washington and Virginia offices.

In addition, eight lawyers were selected as “Lawyers of the Year” for their particular areas of practice. 

August 20, 2014 - Honors & Awards

63 Whiteford, Taylor & Preston Attorneys Listed in Best Lawyers in America, Four Named as "Lawyers of the Year"

Sixty-three lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2015 (copyright 2014 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Maryland, Washington and Virginia offices.

In addition, four lawyers were selected as “Lawyers of the Year” in the Baltimore region for their particular areas of practice.

February 11, 2014 - Honors & Awards

Fifty-Four Whiteford Attorneys Named Super Lawyers and Rising Stars in Maryland

Whiteford, Taylor & Preston is pleased to announce that 54 of its Maryland-based attorneys are listed among the 2014 Super Lawyers and Rising Stars.

The firm is particularly proud of the young lawyers who are recognized as “Rising Stars” and the three partners who received special recognition -- Edward Buxbaum and Dwight Stone in the Top 100, and Mary Claire Chesshire in the Top 50 Women.

August 15, 2013 - Honors & Awards

61 Whiteford, Taylor & Preston Attorneys Listed in Best Lawyers in America; Nine Named as "Lawyers of the Year"

Sixty-one lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2014 (copyright 2013 by Woodward/White, Inc., of Aiken S.C.). The lawyers selected are based in the firm’s Maryland, Washington and Virginia offices, including the firm's new Roanoke office.

In addition, nine lawyers were selected as “Lawyers of the Year” in their jurisdictions and areas of practice.

December 31, 2012 - Honors & Awards

Sixty-Four Whiteford Attorneys Named Super Lawyers and Rising Stars in Maryland, Delaware, Virginia

Whiteford, Taylor & Preston is pleased to announce that 64 of its attorneys are listed among the 2013 Super Lawyers and Rising Stars in three states.

The firm is particularly proud of the young lawyers who are recognized as “Rising Stars”; the four partners who are listed in the Top 100 in Maryland – Edward Buxbaum, Edwin Fee, William Ryan, and Dwight Stone; and the 16 who are named for the first time this year.

October 17, 2012 - Honors & Awards

60 Whiteford, Taylor & Preston Attorneys Listed in Best Lawyers in America Five Named as "Lawyers of the Year"

Sixty lawyers from Whiteford, Taylor & Preston have been selected by their peers for inclusion in The Best Lawyers in America® 2013 (copyright 2012 by Woodward/White, Inc., of Aiken S.C.).

This represents an increase of seven over last year.  The lawyers selected are based in the firm’s Maryland, Washington and Virginia offices.

In addition, five lawyers were selected as “Lawyers of the Year” in their jurisdictions and areas of practice.

July 30, 2012 - Honors & Awards

Whiteford, Taylor & Preston and 14 Partners Named as Leaders in the Legal Profession by Chambers and Partners

Whiteford, Taylor & Preston is pleased to announce that Chambers and Partners has again ranked the firm highly in its 2012/2013 list of America’s leading firms and business lawyers. 

In addition, fourteen of the firm’s partners received individual recognition, including Kevin Hroblak, who was rated this year for the first time in the Litigation category.  Mr. Hroblak is co-chair of the firm’s Litigation Department and a leading member of the Business Reorganization and Bankruptcy Litigation practice.

December 20, 2011 - Honors & Awards

Forty-Six Whiteford, Taylor & Preston Attorneys Named Super Lawyers and Rising Stars in Maryland; Five in Maryland Listed in “Top 100”

Whiteford, Taylor & Preston is pleased to announce that 46 of its attorneys are listed among the 2012 Maryland Super Lawyers and Rising Stars.

The firm is particularly proud of the five who are listed in the Top 100 in Maryland – Edward Buxbaum, Edwin Fee, Paul Nussbaum, William Ryan, and Dwight Stone. Selection of the Top 100 lawyers in a jurisdiction is strictly based on the highest scores in the Super Lawyer judging process, and Whiteford is one of the two firms with the most names on the list.
July 8, 2011 - Honors & Awards

Whiteford, Taylor & Preston and 13 Partners Named as Leaders in the Legal Profession by Chambers and Partners

Whiteford, Taylor & Preston is delighted to announce that Chambers and Partners has highly ranked the firm and 13 of its attorneys in its 2011 list of America’s leading firms and business lawyers. 

Newly rated this year was Joseph Mezzanotte, co-chair of the firm’s Real Estate practice.

As in the past, the firm was recognized in Maryland in six separate categories of practices. As before, the firm’s Bankruptcy Litigation practice is the only one in Maryland ranked in Band One, the highest rating. 

May 9, 2008 - News

Whiteford, Taylor & Preston Announces Management Changes

As it celebrates its 75th anniversary this year, Whiteford, Taylor & Preston LLP is delighted to announce its new leadership team.

Having completed four terms as Managing Partner, Albert J. Mezzanotte, Jr. will serve one more year as the Firm's Managing Partner and transition those duties to Martin T. Fletcher. Mr. Fletcher is a present member of the firm's Management Committee and after serving a one year term as Managing Partner Elect will then commence a three year term as Managing Partner.
September 11, 2007 - Honors & Awards

26 Whiteford, Taylor & Preston Attorneys Named Best Lawyers in America

Twenty-six lawyers from Whiteford, Taylor & Preston were recently selected by their peers for inclusion in The Best Lawyers in America® 2008 (Copyright 2007 by Woodward/White, Inc., of Aiken, S.C.) This represents an increase of 13% from prior listings.

October 17, 2006 - Honors & Awards

36 Whiteford, Taylor & Preston Attorneys Named Maryland Super Lawyers

Whiteford, Taylor & Preston LLP (WTP) is pleased to announce that 36 WTP attorneys have been named in Maryland Super Lawyers publication. Maryland Super Lawyers will appear in a special advertising section in the January 2007 issue of Baltimore Magazine and in the Maryland Super Lawyers magazine.

September 24, 2003 - News

Whiteford, Taylor & Preston Attorney Named to Villa Julie College Board of Trustees

Mary Claire Chesshire, a partner with Whiteford, Taylor & Preston LLP., has been named to Villa Julie College's Board of Trustees. She is a 1982 graduate of Villa Julie's paralegal studies program and currently serves on Villa Julie's Alumni Advisory Board. She has previously lectured for the paralegal studies program.
May 23, 2003 - News

WTP Elects New Partner

Whiteford, Taylor & Preston L.L.P. is pleased to announce that Mary Claire Chesshire has been elected a partner of the firm.

Mary Claire Chesshire practices in the Employee Benefits group. She received her B.S. from Johns Hopkins University in 1989 and graduated cum laude from the University of Baltimore School of Law in 1993. She is admitted to practice in Maryland and is an active member of the Maryland State Bar Association and the Baltimore City Bar Association. Mary Claire is resident in the Baltimore office.