AN INTERVIEW WITH STEPHANIE DIGIUSEPPE

" All lawyers think analytically…but to beat your opponent in litigation you really have to think creatively as well "

Stephanie graduated from McGill University, having studied philosophy and English literature. A philosophy course in deductive logic inspired her to take the LSAT and she went on to receive a J.D. from Osgoode Hall Law School. Between her undergraduate degree and starting law school, she worked a summer on Bay Street and though she enjoyed the content, she knew the lifestyle was not for her. Stephanie articled at criminal defense firm Derstine Penman, worked there for 5 years, then left and started her own practice, joining Ruby Shiller shortly afterwards.

Why Litigation?

Stephanie’s career advice is to “think more about what you want your days to look like,” more than any other factor. Litigation offers variety, something she values highly. In criminal litigation, days alternate between being in court for procedural or substantive matters and being at the office writing and reading disclosure. If you thrive on an energetic, varied lifestyle, litigation is a good place to be.

One of the biggest reasons Stephanie did not pursue a career on Bay Street was not wanting to “wait a decade” to be in court. New lawyers on Bay Street typically only have low-level involvement, and it takes time to work your way up to serious in-court responsibilities. She does highlight that Bay Street is good for mentorship and having senior lawyers monitor your work. But if you want a great deal of independence, criminal defence is excellent for that.

Essential Skills

Curiosity is huge. In litigation, the subject matter of what you deal with changes every day. You engage with issues of science and social science, and philosophical questions about what the law should look like. For example, an interest in thinking about how different fields converge is integral to the regulatory cases Stephanie has worked on, such as defending doctors or other medical professionals accused of professional misconduct.

Creativity. “All lawyers think analytically…but to beat your opponent in litigation you really have to think creatively as well.”

Resilience and the ability to disconnect from your work are also important — so that you can have a personal life and not be consumed thinking about your cases while at dinner with family. Stephanie says this skill is learned over time.

Emerging Developments in Criminal Litigation

Stephanie believes we are in a period where the courts are paying increasing attention to the sentencing process. There used to be a real imbalance: three months would be spent to determine if the accused was guilty at trial, and then only two days on sentencing them. Stephanie attributes this to the judicial toolbox for sentencing being sparse. Judges do not have a lot of sentencing options available to them, so the major issue being determined is how long a person will spend in jail. We are starting to see a trend towards restorative justice, but we have a long way to go.

Other emerging features of sentencing include the consideration of evidence of race and cultural impact as well as mental health and trauma — and, specifically, bringing these factors together to create sentences that are more useful in terms of rehabilitating people. Stephanie also highlights that criminology and the social sciences are growing in their understanding of the role the state plays in manufacturing crime through systemic racism and the other ways in which it decides how opportunity is distributed.

The Media as Part of Litigation Strategy

Stephanie sees the media as one of the tools in her litigation strategy. Her principle when working on high profile cases is to never feel pressured to engage with the media if it will not advance your client’s position. For defense lawyers who choose to do so, correcting any errors made in reporting about your client is a minimum. Beyond that, it depends on the needs and circumstances of the case.

In civil litigation against the province or a municipality, media coverage directed at the issue can be a strong impetus for the government to settle. In that sense, engaging the media can be very useful. In one class-action lawsuit Stephanie was involved in, regarding abuses at a residential school for the blind and deaf, there was a tough legal battle, but turning public attention to the civil rights issues and getting the media to engage with them was an important goal in its own right for her clients. In another case, Stephanie suggested that her client, the accused, engage with the author of a multipart media piece scheduled to be released in advance of a jury trial. Her aim was to temper as much as possible the otherwise sensationalized piece that would come out.

Progress on ending solitary confinement

Stephanie describes ending solitary confinement as the most frustrating area of all her work. While there has been headway in capturing public and government attention, she is not convinced that the changes so far have made a tangible impact on the people in segregation. Segregation persists sometimes under a different name or slightly different parameters so it does not run afoul of the law. Provincial offenders are especially at risk — once they go into a solitary/segregated unit, it is an informational dark hole with hardly any oversight.

One area where Stephanie remarks there has been good progress is getting sentences reduced based on time served in segregation. However, getting remedies for segregation after the fact are not big wins. Stephanie emphasizes that time in solitary needs to be prevented before a person’s mental health is degraded to such a degree that a court provides remedy after the fact.

Underpinning these issues is the fact that correctional institutions often lack options beyond segregation when an inmate acts out. Stephanie also criticizes the culture of complacency within corrections and the restricted ability of judges to make binding orders regarding the treatment of a person inside an institution.

Pandemic innovations that will remain post-COVID

“We were living in the 1980s before COVID.” Stephanie describes the norm of paper filing and how some offices only accepted faxes before the pandemic. She thinks technological modernization like e-filing and virtual appearances will remain after the pandemic ends. She is glad, since members of the defense bar sometimes had to drive to three different courthouses a day to appear before judges for simple procedural matters. Now, they can do that over Zoom. By contrast, she thinks a lot is lost with virtual trials and so they will not stick around.

How Stephanie's Workplace Works to Advance EDI

Stephanie describes how Ruby Shiller Enenajor DiGiuseppe Barristers focuses on outward-facing equity, diversity, and inclusion (EDI) work. The firm advocated in favour of the proposed Statement of Principles at the Law Society of Ontario by talking to the media and campaigning for it. RSED partner Clayton Ruby worked on a media campaign and in litigation against Trinity Western’s exclusion of gay students. The firm as whole is involved in promoting the inclusion of evidence of race and cultural factors in sentencing for Black offenders. Stephanie and her colleagues, Annamaria Enenajor and Lisa Jørgensen, have also written a chapter in a book meant to help practitioners employ this practice in sentencing hearings.

Stephanie’s advice for law students

Work on relationship building in law school, especially with professors who are practitioners in an area you want to practice. Get involved with bar organizations, such as the Criminal Lawyers’ Association as a student member. Stephanie also recommends “law twitter”, saying she found a wonderful community where a lot of useful interactions between students and lawyers take place: “I’ll read a post and think, wow, that’s such an insightful post, let me see who wrote it, and it’s a 1L at the law school! Through that there’s a great connection that I don’t know exists in any other forum day to day”.