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Scott C Cashman.

Tax Manager

Scott C. Cashman

Tax Manager


Scott Cashman is the Tax Manager for the firm’s Estate, Financial and Tax Planning practice area. He is responsible for the preparation and oversight of all fiduciary, individual and corporate income returns as well as estate and gift tax and nonprofit tax compliance. Scott also represents clients in audits before federal and state taxing authorities.

In addition to working with the Estate, Financial and Tax Planning practice area, Scott trains new associates in tax compliance as well as serves as a tax and accounting resource for the entire firm.

Prior to joining Bowditch & Dewey, Scott’s law practice focused on domestic and international tax planning and compliance for individuals, trusts and estates, estate & gift taxation, intergenerational wealth transfer strategies and the structuring of domestic business transactions.

Scott retired as a Lieutenant Colonel from the Army Reserves after 31 years of combined Reserve, National Guard and Active service which included Uzbekistan and Afghanistan as part of Operation Enduring Freedom. Scott was most recently assigned to the Office of the Judge Advocate General Legal Assistance Policy Division at the Pentagon. Scott was also appointed and served as a Special Assistant United States Attorney for the Northern District of New York from 2003-2004.

Scott is also a co-editor of the Don’t Tax Yourself blog.


  • Member, City of Worcester Parks and Recreation Commission 2015-Present


  • Judge Advocate with rank of Lieutenant Colonel, US Army Reserves 1999-2022
  • Member, City of Worcester Planning Board 2005-2011

Articles + Talks



  • “2021 Income Tax Course,” U.S. Army Judge Advocate General’s School and Legal Center, November 30 – December 3, 2021

Bar Admissions

  • Massachusetts
  • U.S. District Court, District of Massachusetts
  • U.S. District Court, District of Northern New York
  • U.S. Tax Court
  • U.S. Court of Military Appeals


  • J.D., New England School of Law
  • M.S., Taxation, Bentley University Graduate School of Business
  • CFP, College for Financial Planning
  • B.A., Economics, Framingham State University
  • Significant net-worth client, including a high seven-figure income, in an income tax audit before the IRS Worcester office. The audit raised a number of issues, including substantial capital gains, installment sale income and charitable contributions arising out of the client’s multi-million dollar payout from the sale of the client’s former employer. The engagement required representation before several audit conferences and intensive document production and resulted in a “no change” report issued to the client.
  • Advised an out-of-state engineering firm on multi-jurisdiction tax issues. Client is headquartered outside of Massachusetts but recently established an office in Massachusetts and became registered to do business as a foreign corporation. Several of the shareholder employees were residents of other New England states. Drafted an advisory for the client employer on payroll tax obligations as well as potential tax reporting and liabilities with respect to each shareholder employee in each jurisdiction.
  • Conducted a compensation analysis and private inurement testing for a prestigious New England liberal arts college. As part of the engagement, we reviewed the total compensation of the College’s highest earning employees, reviewed the adequacy of internal record keeping, determined which employees were considered “disqualified employees” under current IRS Regulations, and prepared an opinion for the College’s compliance with IRS Regulations.
  • Advised a recently widowed client on income and estate tax issues. The client, who is in her early 80’s, had depended upon her recently deceased husband to manage the couple’s finances. Their net worth was approximately $2 million. We identified several income and Massachusetts estate tax issues. As part of the engagement, we reviewed and revised the client’s estate tax plan, created an LLC to hold a small rental property, and advised the client on a lifetime gifting plan. The client was so pleased with our service that she decided to have Bowditch  prepare her income tax returns.
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