Jessica Winfrey

Manager of Tax and Financial Services, AttorneyJessica Winfrey - Manager of Tax and Financial Services, Attorney

Jessica is one of those rare people who knew what she wanted to do from a very young age while growing up in a small-town in rural Michigan. She wanted to be a lawyer.

Fast forward to law school, and you would have found her working with domestic violence victims facing eviction from their homes. For Jessica, being a part of helping families find safety and recover from a bad chapter led her to a critical decision: she would only work in a role where she was truly helping people. And that career choice has been extremely rewarding.

She understands that many of her clients at TTD are facing the most difficult period in their lives and might feel like they will never dig themselves out from their complicated tax issues. They need a great defense team to fix their problems, so she knew it would be a natural transition for her from law school to take a position like this where she can help people get back on their feet.

In her spare time, Jessica loves reading historical fiction and traveling abroad. Spain and Italy top her list of favorite travel spots.

Academic Background:

  • JD, New England School of Law
  • Universitat Pompeu Fabra (Barcelona, Spain)
  • University of Oxford
  • BA, Western Michigan University

Volunteer Work/Community Involvement:

  • Cornerstone Community Outreach
  • Amigos de Santa Cruz

Professional Memberships/Associations:

  • Illinois State Bar Association
  • Women’s Bar Association

Former Employers:

  • Commonwealth of Massachusetts


  • United Nations Foundation Scholarship
  • Dean’s Scholarship Award Recipient (3 years), New England School of Law

Direct Dial #: (312) 940-1592

Hear from Our Satisfied Clients

  • The Tax Defenders I really, really appreciate it. I would recommend them to anyone, to anyone.
  • The Tax Defenders I would recommend you to anybody else who needs help with their income tax problems
  • The Tax Defenders I want to thank all of you for everything you’ve done for me. I’m finally clear of this hanging over me for a long, long time.
  • The Tax Defenders It was awesome how they took care of everything and worked with my finances. They were able to resolve 100% of the money owed. I am glad that I called them.
  • The Tax Defenders With one phone call, and in 15 minutes, they clearly explained my options, even though they were not able to help me. Who does that???
  • The Tax Defenders The Tax Defenders handled my case professionally and efficiently
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