The following is an excerpt from Practice Perspectives: Vault's Guide to Legal Practice Areas.
Doreen M. Rachal focuses her practice on white collar criminal defense, internal investigations, and criminal and civil government investigations. She represents companies and individuals in matters involving civil and criminal investigations, including grand jury matters and enforcement actions conducted by the DOJ, the SEC, and state government agencies. She has extensive experience conducting complex global internal investigations and advising boards on internal compliance programs. Her clients span a variety of industries, including financial services, life sciences, technology, and maritime. Doreen is a member of Sidley’s white collar defense and investigations, healthcare, and securities enforcement and regulatory groups.
Prior to joining Sidley, Doreen served as an assistant U.S. attorney at the U.S. Attorney’s Office for the District of Massachusetts in the Affirmative Civil Enforcement Unit where she handled qui tam actions and prosecuted healthcare fraud matters involving potential violations of the False Claims Act. Prior to joining the Affirmative Civil Enforcement Unit, Doreen served in a supervisory capacity as the Chief of the Asset Forfeiture Unit. In this role, Doreen prosecuted civil and criminal asset forfeiture cases involving money laundering, drug trafficking, healthcare fraud, and securities violations. During her tenure at the U.S. Attorney’s Office, Doreen successfully handled several trials as lead counsel.
Describe your practice area and what it entails.
I handle white collar criminal defense matters, which include internal investigations and criminal and civil government investigations. These matters include representing companies or individuals in grand jury matters and enforcement actions conducted by the DOJ, the SEC, and state government agencies. Matters in these areas typically require crisis management; fact gathering; complex legal analysis; knowledge of various areas of the law; solutions-focused strategies; knowledge of the criminal process from arraignment to sentencing; motions practice experience; trial experience, if applicable; and the ability to connect with people, clients, and the government.
What types of clients do you represent?
I represent clients across industries, including life sciences and healthcare, financial services, technology, and maritime. Although my clients tend to be companies within these industries, I have also represented individual clients in criminal matters and government investigation matters.
What types of cases/deals do you work on?
Generally, my practice focuses on conducting internal investigations and handling government inquiries at all levels (local, state, and federal) across the United States. Some of my current cases have a global reach, and for those cases, I work with colleagues in Europe, South America, and the Asia-Pacific (APAC) region to surround our clients with the expertise relevant in these areas of the world. My current cases tend to focus on aspects of healthcare fraud, and I have also handled numerous investigations on behalf of clients involving financial fraud and aspects of civil and criminal forfeiture.
How did you choose this practice area?
At my previous firm, I assisted with an internal investigation as a junior associate. This experience was without a doubt the most rewarding and enriching one I had during my time there. While in Massachusetts, I also attended various forums and seminars that concentrated on federal criminal practice, and it was through that exposure—in addition to the mentoring received by several lawyers in my cabinet—that I developed an understanding of how best to have a successful criminal defense practice. This is what led me to pursue a position as an assistant U.S. attorney. Moreover, the incredible experience I had as an assistant U.S. attorney reinforced my strong desire to continue my work in this practice area.
What is a “typical” day like and/or what are some common tasks you perform?
My typical day includes a large number of phone calls either advising clients on current matters or performing various aspects of internal investigations. I am responsible for reviewing and analyzing documents and/or government requests, meeting with my Sidley colleagues who are staffed on my current matters, conducting interviews either on Zoom or in person at client sites, drafting briefs for current matters in court, and/or preparing for oral arguments.
What training, classes, experience, or skills development would you recommend to someone who wishes to enter your practice area?
For junior lawyers interested in this particular practice, I would highly recommend prosecutorial experience at some point in their legal career. For law school students interested in this practice, it is beneficial to embrace judicial clerkships and take advantage of any opportunities that provide writing experience and complex legal research opportunities.
What do you like best about your practice area?
I thoroughly enjoy every aspect of white collar criminal defense work. My former prosecutorial experience in the U.S. Attorney’s Office in the District of Massachusetts was one of my favorite and most impactful career opportunities. Working with agents across many federal government agencies—and, in particular, developing investigations and cases—allowed me to grow both professionally and personally in many ways that have allowed my defense practice to evolve throughout the years. The investigatory aspects of being a former prosecutor—namely, delving into who, what, when, where, and why (at the very least)—are very similar to those involved in handling internal investigations and government inquiries. I take great satisfaction in working collaboratively with clients with responding to and handling crises, advising clients on complex white collar matters that arise, and most of all, helping clients navigate ways that avoid similar situations in the future.
What are some typical tasks that a junior lawyer would perform in this practice area?
The typical tasks a junior lawyer would perform in this particular area vary based on the matter. However, generally, for each matter, as it relates to conducting internal investigations, a junior lawyer may assist with document review and collection; prepare for investigatory interviews, including drafting portions of interview outlines; analyze information received through interviews and documentary review and assist with the assessment of risk and potential remedial measures; and assist with the drafting of reports relative to the client’s potential risk areas and recommended potential solutions. As it relates to investigations that are commenced by government agencies, a junior lawyer may assist with information collection, including document collection and review, interviews of key client personnel who may be the target of the investigation, and assessments related to the government requests, as well as responses to such requests. Additionally, depending on level of seniority, a junior lawyer may participate in client interviews and/or conversations with government agencies. For active matters that are being litigated in court, junior associates may assist with case law research, draft portions of briefs, and assist with oral argument preparation and, if relevant, trial preparation.
What kinds of experience can summer associates gain in this practice area at your firm?
Similar to tasks that a junior associate would undertake in this area, I strongly believe in giving summer associates a glimpse into the type of work and assignments they would be taking on as a junior-level associate. These tasks would include performing document review; conducting case law research on cutting-edge, complex legal issues relevant to the matters we are currently working on; and drafting research memoranda that help our team to provide litigation risk assessments to our clients. Most importantly, I strongly believe that summer associates—as well as junior associates—should receive opportunities to observe client meetings, court hearings, and internal team meetings to discuss developments in cases. These observational opportunities provide meaningful professional growth to both summer associates and associates at all levels.
How important is prior criminal law experience (e.g., working for the prosecutor’s office or district attorney) in paving a successful career in white collar defense?
Prior criminal law experience is critical—although not determinative—in paving a successful career path in white collar criminal defense work. Lawyers who have prior prosecutorial experience are able to leverage their knowledge and skills in effective ways that are beneficial to clients, including but not limited to particularized knowledge regarding the ways in which government agencies handle and perform investigations. Additionally, lawyers who have this prior experience often leverage their understanding of the legal system from a prosecutorial lens, allowing for more effective resolution and the creation of stronger defense strategies on behalf of clients. Moreover, because most prosecutors tend to be before judges frequently, this prior experience can be very helpful when clients have matters before these same judges, as the lawyer may have developed particularized knowledge on what may be effective—or ineffective—which can have an impact when developing an effective defense strategy.