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Our Support Team: Maryland Law Firm Trainor, Billman, Bennett, Milko & Smith

Darlene Ruggiero

Darlene Ruggiero, our office manager, has been with the firm as long as the founding partners. She began working with us in earlier iterations of the firm when she was 17; suffice to say that her daughter, born during her employment with us, now has a PhD, and is married. In the early days, Darlene kept our lights on by careful money management, and has evolved along with the now sophisticated financial protocols necessitated by our firm’s growth over the years. She manages our firm revenue, pays our bills, and works with clients to help them pay their invoices in the most efficient and manageable ways. We would be lost without her. She was thrilled to recently become a Grandma.

Sarah Middel

Sarah Middel is our intrepid paralegal. She is in charge of collecting, sorting and organizing client and opposing party documents. She has a near-photographic memory and is our go-to resource person for locating tiny information bytes within the massive bulk of documents accumulated in any given case. She has mastered spreadsheet design and display and is often responsible for summary displays that we frequently introduce into evidence or use in mediations to demonstrate financial or chronological trends and patterns that are often instrumental in prevailing in a case. She is also our on-site techie, helping lesser inclined firm members with their computers, software, and the office network. We would be lost without her, too.

Paul Pope

Paul Pope is our Man Friday. He is first and foremost a people-person, and is usually the first person clients and other attorneys talk to when they call our office. He is patient, kind, and compassionate and conveys those qualities in each and every interaction, whether in person or on the phone. He keeps our office organized and welcoming, assuring that our visitors are comfortable and relaxed from the minute they walk in our door. He had no legal experience when he came to us, but has become conversant in “legalese” and became so interested in the practice of law that he completed his paralegal degree. His expanding knowledge about what we do and why we do it has allowed him to become more effective in his role with our firm, our clients and our colleagues. We would be lost without him, as well. You may be noticing a trend, here…

Carol Downey

Carol Downey is our newest legal assistant. With over 30 years of experience in family law, she has capably jumped in to assist with a burgeoning caseload and all of the attendant paperwork, pleadings, discovery and production and is now fully engaged in handling client communications and managing paperwork. In her spare time, Carol enjoys spending time with her husband, children, and grandchildren, baking, fishing and crabbing and puttering in her garden.

Phoebe, Phineas, and Chloe

In keeping with our relaxed firm culture, we often have canine company in our offices. All three of the office dogs are well-behaved, and are never introduced to visitors unless we are asked to do so, but we are happy to include them in meetings upon client request. They provide a sense of “normal” to our office days and keep us humble. We occasionally rely upon them for second opinions.

Schedule a Consultation at our Annapolis Office Today

At the Maryland law firm of Trainor, Billman, Bennett, Milko & Smith, LLP, our skilled and experienced attorneys can assist you with your family law or criminal defense case. Whether your case is related to divorce, family law or federal or state crimes, we can help. To schedule an initial consultation to discuss your needs, contact us online or call our Annapolis office at 410-280-1700.

Our Support Team: Maryland Law Firm Trainor, Billman, Bennett, Milko & Smith

Darlene Ruggiero


Darlene Ruggiero, our office manager, has been with the firm as long as the founding partners. She began working with us in earlier iterations of the firm when she was 17; suffice to say that her daughter, born during her employment with us, now has a PhD, and is married. In the early days, Darlene kept our lights on by careful money management, and has evolved along with the now sophisticated financial protocols necessitated by our firm’s growth over the years. She manages our firm revenue, pays our bills, and works with clients to help them pay their invoices in the most efficient and manageable ways. We would be lost without her. She was thrilled to recently become a Grandma.

Sarah Middel


Sarah Middel is our erstwhile paralegal. She is in charge of collecting, sorting and organizing client and opposing party documents. She has a near-photographic memory and is our go-to resource person for locating tiny information bytes within the massive bulk of documents accumulated in any given case. She has mastered spreadsheet design and display and is often responsible for summary displays that we frequently introduce into evidence or use in mediations to demonstrate financial or chronological trends and patterns that are often instrumental in prevailing in a case. She is also our on-site techie, helping lesser inclined firm members with their computers, software, and the office network. We would be lost without her, too.

Paul Pope


Paul Pope is our Man Friday. He is first and foremost a people-person, and is usually the first person clients and other attorneys talk to when they call our office. He is patient, kind, and compassionate and conveys those qualities in each and every interaction, whether in person or on the phone. He keeps our office organized and welcoming, assuring that our visitors are comfortable and relaxed from the minute they walk in our door. He had no legal experience when he came to us, but has become conversant in “legalese” and became so interested in the practice of law that he completed his paralegal degree. His expanding knowledge about what we do and why we do it has allowed him to become more effective in his role with our firm, our clients and our colleagues. We would be lost without him, as well. You may be noticing a trend, here…

Carol Downey

Carol Downey is our newest legal assistant. With over 30 years of experience in family law, she has capably jumped in to assist with a burgeoning caseload and all of the attendant paperwork, pleadings, discovery and production and is now fully engaged in handling client communications and managing paperwork. In her spare time, Carol enjoys spending time with her husband, children, and grandchildren, baking, fishing and crabbing and puttering in her garden.

Phoebe, Phineas, and Chloe

  
In keeping with our relaxed firm culture, we often have canine company in our offices. All three of the office dogs are well-behaved, and are never introduced to visitors unless we are asked to do so, but we are happy to include them in meetings upon client request. They provide a sense of “normal” to our office days and keep us humble. We occasionally rely upon them for second opinions.

Schedule a Consultation at our Annapolis Office Today

At the Maryland law firm of Trainor, Billman, Bennett, Milko & Smith, LLP, our skilled and experienced attorneys can assist you with your family law or criminal defense case. Whether your case is related to divorce, family law or federal or state crimes, we can help. To schedule an initial consultation to discuss your needs, contact us online or call our Annapolis office at 410-280-1700.

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