You, a new captain behind the spinning wheel of a vessel celebrating 40 years of survival in rough waters. Leader to a crew traditionally considered outsiders, forced by societal restrictions and constructed social norms to band together for their survival. Many folks don’t know that pirates, the seafaring outsiders of their day, operated under a democracy with written “articles of agreement” before democracy was even a thing. Leadership by a committee. This is how the new Executive Director of Pride Toronto, Sherwin Modeste, was voted into his leadership role, and this is how he continues to guide the direction of his ship. Democratically and with an empathy no doubt shaped by his personal and professional life experiences.

But his tenure hasn’t been without its own storms. Imagine being an openly gay Black man taking on the role of one of the largest Pride organizations in the world at the height of a global pandemic. How would you navigate your community through a tidal wave of uncertainty? At a time when open assaults are still taking place on 2SLGBTQ+ communities and their relationship with the authorities entrusted to protect them is frayed at best, some would be happy with just keeping the ship afloat. However, my conversation with Modeste reveals a new captain prepared to take this massive ship with rainbow sails past the limits of any known map. Far beyond the virtual and “in real life” confines of a single month in a single neighbourhood every year, because the lives of all the people in the same boat aren’t limited to just 30 days in June and one area of the city.

I spoke to Modeste about some of those life and professional experiences that have prepared him for this new undertaking and discussed the challenges ahead.

Grenada, like many other islands in the Caribbean, makes same-sex relationships criminal acts punishable with imprisonment. What was it like growing up for you in that environment?

Yes, there was some knowledge of this while growing up that I had to deal with. I did everything in my power to not act on it or make it obvious, but from primary school to high school, I got called all the names. I was what we would refer to as metrosexual, so I took care of and groomed myself properly, I wasn’t loud, and I didn’t play cricket and soccer etcetera. I did things that folks would predominantly refer to as ‘feminine, which triggered many folks, so I didn’t build a base of friendship or have a lot of friends. However, I found refuge in the church. Being an altar boy, I just wanted to spend all my time in the church because it was the only place that I felt safe.

That’s interesting because, in the Caribbean, Christianity still takes a very central role in the way people there look at same-sex relationships. But you say you found refuge in the church?

Yes. I found refuge from the community and name-calling. By being active at church, what they saw was a churchgoer who was always willing to help people. Deep down there was a dark side. The feeling that I didn’t want to live, but at the same time, the church was a safe place that took me away from thinking about my situation. There were other names for me like ‘priest’ or ‘father’ as opposed to the derogatory terms.

Did you ever think about the irony that the attitudes espoused by the church were the same attitudes that caused you the most pain?

It didn’t cross my mind then but now on reflection, it’s very obvious. At the same time, the homophobic, biphobic or transphobic sermons weren’t preached in Grenada like in North America. Now times have changed and that may have shifted, but at the time, the persecution of the 2SLGBTQ+ was not as prevalent in the church or on the radio. Most of that persecution came from within circles you knew.

So then you came to Toronto to study Hotel & Restaurant Management before pivoting toward Early Childhood Education. As a Grenadian-Canadian, how does your dual experience influence your identity as a member of the Black 2SLGBTQ+ community in Toronto? In what ways do those experiences intersect or diverge?

Even after moving to Toronto, it was not something I was willing to accept due to my strong Christian upbringing. I got married at a very young age. By the time I was eighteen I was already married and by the time I was nineteen, I had my daughter. That brought me to the place of not being true to myself and others. So I continued to struggle and as a result, I would refer to myself as a guy who was on the down-low. I was playing both sides for a time. I started to get some counselling through friends at CAMH just to be able to rebalance and realize that I was only doing myself and others around me harm. That’s when I decided to live my authentic self. It wasn’t like I left Grenada and boom, everything changed. I continued to struggle and you’re right, the church had a very important role to play in that because I’d left Grenada but I hadn’t left the church. I think as I started to encounter other West Indians that were having the same struggles I was, it pushed me towards the side of advocacy and wanting to provide support or leadership within the community. I began working with the unions and joining different clubs which helped to elevate me as a young Black man so I could provide that support to our community. I saw this as an opportunity to really learn and also give back so that others wouldn’t have to go through some of the same struggles that I was going through.

How long were you married?

For about 6 years.

When you knew what path you were on and you knew that your marriage wasn’t going to work, what was that conversation and split like?

The conversation wasn’t easy to have. Any separation is hard, but separation because of sexual orientation, especially on a Black West Indian woman, is really not easy. I was called all the names and it was a fight. But I give thanks that we were able to reconcile and raise our daughter together. It was something I felt I needed to do because I had to be true to myself to be true and provide support for others. It wasn’t easy but it was necessary.

Before your role as the Executive Director of Pride, you’ve held leadership roles in Labour (unions), Toronto Community Housing and community health services. How do you think those positions prepared you for the role you’re in now?

In all the roles I’ve had, I was always interacting with people. My sense of wanting to give back to the community has always been very important. Dr. Martin Luther King said an injustice to one is an injustice to all. Seeing firsthand the struggles and discrimination, not just on the 2SLGBTQ+ community, but seeing it firsthand on the Black community, women, and Indigenous folks, King’s statement resonated with me to want to advocate for justice at all levels. Being in those positions has equipped me to take on this role. Also having really good mentors and femme-tors has provided me with the foundation to lead one of the largest Pride celebrations in the world. I don’t take that likely.

What motivated you to take on the role of Executive Director of Pride?

In 2019, I went to New York during World Pride and visited the Stonewall Inn on the 50th anniversary of Pride celebrations. Being there pushed me to come back to Toronto to get involved with Pride and make a difference. Because when you think of Pride, you predominantly think of White gay men. But realizing that the founding members of Pride, Trans women of Colour, are not at the forefront, I didn’t want that to be lost. I had the intention of just getting on the board and volunteering and here I am today in a whole different role.

You began your role officially in November of 2020. What are the challenges of navigating Pride through a global pandemic in 2021?

Taking on the role in the middle of a pandemic wasn’t easy but you get the best out of me during difficult times. I think the biggest challenge was just figuring out how to make Pride work and ensure the audience is given the same or better Pride than they would’ve received in 2020 as a result of the pandemic. The challenge was how do I bridge the gap in such a short time? I had new staff, never worked with the organization before, in a very political organization. The eyes of all of Canada are on Pride Toronto. So that political pressure is a motivator that pushes you to work harder. There was also the uncertainty of funding during a global pandemic. Remember, Pride is not all government-funded. Most of Pride’s funding is through corporate sponsorship. But our sponsors came through like never before and even the government stepped up in some cases.

The new location of the Pride Toronto office is located in the MOCA (Museum of Contemporary Art) where you have spaces allocated for creative studios and artist residencies for the LGBTQ2+ community. Why is supporting local creatives of such obvious importance to you?

We must create safe spaces. Many of our LGBTQ2+ community members are very talented but we’ve heard from them that they don’t feel safe. The environments they sometimes find themselves in are not very welcoming. We wanted to create a space where folks could feel safe and not have to spend a lot of money. This was the intent of creating the studio on-site to build the skills of our artists. However, the studio isn’t just for Queer artists. Other folks and agencies can take advantage of it, but we saw this as a great opportunity to help elevate many of our artists.

There was a recent brutal attack on a young gay man coming home from Hanlan’s Point where the victim was taunted with homophobic slurs. What do situations like this say about the need for Pride and a focus on our 2SLGBTQ+ communities?

All of the recent and other attacks we’ve heard about on the community speaks volumes as to why this work needs to continue. Many of the attacks that occur daily go unreported over the fear of being outed. There are a few things that need to happen. We need to see legislation that speaks to hate and hate crimes. Whether it’s homophobia, transphobia, racism, Islamophobia, what have you, once you can name hate there should be legislation that speaks to that. Law enforcement needs to start taking these things seriously. So many of our Trans women are being attacked constantly and the attacks aren’t being taken seriously. Our society also has a role to play. We see faith groups coming together to address racism or Islamophobia, but we cannot sit back and allow hatred of any group of individuals. The community needs to speak out and say this is not going to happen on our watch. If not, this will just continue. There are copycat individuals who, when one person does it, other’s feel like they can do it too. So this is my biggest fear as we continue with Pride month.

During the discussion by prior Pride leadership around the presence of police officers at the parade, there was pushback from within the community from some who felt the Parade was being over-politicized. After the Bruce McArthur case, which is viewed as being mishandled by Toronto Police Services, there was a renewed focus on the relationship between the 2SLGBTQ+ community and the police. What are your thoughts on the importance of political activism and police presence at Pride?

With regards to political activism, this is what Pride was founded on. That will continue and we can’t lose focus on that. I’ve said to folks all we need to look at is what happened in the U.S. Before the current administration we had four years of very backward legislation. All it takes is one election and Toronto, Ontario, or all of Canada can find itself in a similar situation. Concerning relationships with the police, at Pride Toronto, we know we have to in some capacity work with the police. There was a very democratic process by which police involvement in Pride would be arranged. It was done through a membership vote and that is something I will respect. However, I think the police also need to do their part to acknowledge some of the wrongs done to the community and, where they can’t fix them, they need to apologize. It’s really important that the community knows and feels this. When you lose the trust of a group of individuals you don’t just get that trust back. You have to earn that trust. I think it’s really important that the police earn back the trust of the community, and when the community decides it’s fitting to welcome the police back into the community, then the police can be welcomed back. I get asked a lot for my thoughts on this matter. My thoughts are it was a decision made based on a free and democratic vote where nobody was pressured and I will respect that vote. But for Pride to get City of Toronto permits, there has to be police involvement. So when the police are at the parade, what is their role? Is the role of the police very different from harm reduction staff? My role is to try and figure out how to work with the system to make sure we aren’t causing more harm to the community. I see myself playing a very important role in that as Executive Director.

As someone who is both Black and gay, how do situations like the “Neptune 4” case or the case of Regis Korchinski-Paquet reinforce the importance of intersectionality at Pride and do you think that the White 2SLGBTQ+ community are intersectional enough in their thinking?

I think it’s really important for the community to understand that when you’re racialized and 2SLGBTQ+ or someone with a disability and queer, there are so many layers. Understanding those intersections is very important. I don’t think that we’ve done that justice and it’s why we continue to have these struggles today, even within the 2SLGBTQ+ community. Two-spirited folks have been left behind. Racialized folks have been left behind. In some cases, women have been left behind. Because oftentimes when you look at Pride, what do you see? A bunch of men with perfect six-pack abs and is that what the community really is? The answer is no, but we’ve continued to project that image. So we need to take a few steps back to understand the intersections within the community and how to make sure they are all included. As the Executive Director of Pride, I now have thirteen advisory groups. From seniors to youth, persons with disabilities, BIPOC and so on. It’s necessary to not just hear from them, but get their ideas into programs. This is definitely important to me and one of the pieces I am committed to in terms of ensuring that all the voices of the community are heard and also put into action.

Where would you like to see Pride go from here?

Under my leadership at Pride, I would like to see an organization that is providing some sort of service 24/7, 365 days of the year. Pride is more than just about a festival. We have Pride month but the issues don’t start on June 1st and end on June 30th. So we must do our part to ensure voices are heard all year. At the same time, I think Pride needs to be moved out of downtown. This summer, I’m proud that we’ve had socially distanced events in every ward in Toronto. So when I’m in Scarborough, Etobicoke, East York or North York, and I’m hearing happy families saying thank you for coming out here, I know I want to continue that in some capacity. We know that the historic village will remain where it is and be the nucleus of Pride but how do we take Pride outside of the village? Also, how do make sure Pride is reflective of the community? Currently, we have a board of directors and a staff complement that is majority BIPOC and it speaks to the direction the organization is going and will be. Last but not least, it’s also about financial stability, transparency and accountability of the organization. I know that as a Black, gay man, everyone’s eyes are on me because I’m in the leadership role. So I know I have to work twice as hard and that accountability and transparency within the organization are going to be really important under my leadership.

Watch the Digital (Virtual) Pride Parade (Sunday June 27, 2021 at 2 pm EDT)

https://www.pridetoronto.com/event/pride-parade/