Ten Years of Gender Justice: A Conversation with Oliver Webb


In celebration of Gender Justice League’s 10-year anniversary, this blog post is part of a series called Ten Years of Gender Justice, a commemoration of some of the key players throughout GJL’s history. Throughout this series, we’ll highlight a few of the collaborators, organizers, and activists who have worked within or alongside GJL to make strides in advancing gender justice in Washington State and beyond. 

Oliver Webb has been part of the Gender Justice League & Trans Pride Seattle family since 2017, holding multiple roles as a board member and TPS organizer covering and overseeing accessibility, security, and operations efforts. Oliver also leads security for various other prides and events throughout the region; advocates for gender, accessibility, and housing needs for community members; and is the Executive Director of Diversity Alliance of the Puget Sound: a nonprofit supporting trans and gender diverse adults with support groups, advocacy, and financial aid. 

Note: this interview was conducted in May 2023.


How did you first get involved with GJL? 

I knew that I was trans pretty early on, as a very young child. I attempted to come out to my family and was told that I was not trans or queer. Eventually, I was able to be out as queer [in adulthood]. I asked myself over the years whether or not I was trans. I had been ingrained in the queer and trans community and thought I was a very good ally, as many of us would later realize was very funny after we cracked our eggs. When I finally figured it out in 2017—I think it was around Trans Day of Visibility—I did what I was used to, which was to start volunteering. 

I’d been an activist since single digits. I had been volunteering in the queer community in Seattle since probably my early 20s, maybe even before that. I had reached out to organizations and tried to find resources, but there wasn’t really anything for trans masc individuals at that point. Gender Odyssey (GO), Seattle Pride, and Trans Pride Seattle (TPS) were the three that I volunteered for first. I can’t really do anything halfway. 

Oliver Webb marches in Trans Pride Seattle (2018). Photo by Andie Deroux.

I went to my first Trans Pride Seattle that summer [of 2018]. I planned on just attending and I remember being fairly scared, but also [comforted by being in] the community I had been part of for a very long time, where my friends were. I just showed up and let the cards fall where they were going to fall. I remember showing up at the beginning of the march, stuck in that little corner on Thomas, off of Broadway. I was at the beginning of the march because I have a disability, and Danni [Askini] handed me a sign and asked if I would help lead the front of the march. I was helping with the Black Lives Matter contingent at that time because no one was able to help organize. So, that was the first time I helped volunteer with GJL. 

I continued to volunteer with Seattle Pride and became a major volunteer there, as well as a major volunteer at GO until they left [Seattle], and I fell in love with GJL. I became good friends with Elayne [Wylie], and Sarah Abshire who was on the board at the time.

Sarah Abshire and Oliver Webb at the Gender Justice Awards (2019).

On that Saturday of Pride weekend [2019], Sarah Abshire sat me down at The Wild Rose and asked me to join the GJL board. I joined the board that August. When COVID hit, I experienced lots of mental health things and isolation, so I stepped off the board and took a few months off to settle in, heal, and move forward. 

I was asked to join the board and assist at another organization (at the time named Gender Alliance of the South Sound, now named Diversity Alliance of the Puget Sound) and I ended up having to take over that board after we lost the entire board to COVID, unfortunately. I spent three years building up that organization, and I have just accepted a position as the Executive Director. 

Oliver Webb backstage at Trans Pride Seattle (2023). Photo by Alex Garland.

I helped organize the TPS march for many years. I have been the Accessibility Coordinator for the majority of the years I’ve participated, or at least assisted with accessibility. I was on the security team in 2019 as Roaming Lead, and in 2022 I functioned as Head of Security (we didn’t have an in-person TPS between 2020-2022 due to COVID). 

Now that we’re well into the COVID pandemic, things have stabilized. This year, my organization Diversity Alliance of the Puget Sound (DAPS) is a top sponsor of Trans Pride Seattle; I am the Operations Director of Trans Pride Seattle, overseeing all security and accessibility efforts; and I’ve been able to return to the GJL board. 

(Sarcastically) So, I’m not really involved with GJL much these days at all, whatsoever (laughing). 

Why did you decide to become so involved in queer & trans organizing? 

I have always volunteered, and I think early on a lot of that had to do with trying to get out of my house. My house, and school, weren’t safe spaces. I had a really tough childhood. I was a foster kid, and I had been taken away from my family of origin due to abuse. I wasn’t allowed to transition or come out.

Volunteering meant I got to get away. Also, you tend to get fed when you volunteer, so sometimes I got food there, too. Because I was helping, getting food, and getting out of an unsafe space, volunteering became a routine I started very young. As I became older, it helped that I had a community and a support system [built through volunteering]—people that mattered in my life.

GJL board members and co-executive directors pose at the Gender Justice Awards (2019).

After volunteering in a community for decades, it became my lifeline. That was the community that had held me up, that had saved my life over and over. The queer community in Seattle was my friends, the people I worked with, the people I went to school with, and the people that will stand next to me in my wedding. I found families at GJL. I found families at Seattle Pride. I found families at Gender Odyssey. 

I don’t do anything without thinking it through and deciding whether or not it is worth my time and energy, because I don’t have time to add something else to my plate that isn’t going to be beneficial for me, for my community, and for my energy. So, when I joined the GJL board, I believed in what Danni [Askini] had built, what they were building, and what could come after it. I was young and idealistic and had all these things I wanted to do. I stepped onto that board wanting to make a change in my city and in my community. I found mentors that helped me become a better activist, a better person, and a better friend. I had no idea what I was doing when I stepped on that board—I didn’t understand what a board was. I didn’t understand a lot of what GJL did. I didn’t understand what nonprofits did. I didn’t understand that we had grant [requirements and funders] that we had to answer to.

Oliver Webb speaks at the Gender Justice Awards (2019).

I learned so much in the first 10 months on the board at GJL that has helped propel me in everything I do now. In the last three years, it helped me learn how to run an organization and to be a true community leader. It helps me every day in serving this community. 

I have so much more to learn, obviously, and will continue learning and growing every day. I am so thankful that I was able to step onto a board where I was able to learn. That is the board I aspire to lead at DAPS. I hope that the leaders that come after me lead a board where people can learn and grow from current leadership; where they don’t feel that they have to come on to it already seasoned board members; where it is okay to make mistakes; where it’s okay to not know what you’re doing; where you can find mentorship. 

Oliver Webb, Elayne Wylie, and Danni Askini pose together after Trans Pride Seattle (2023). Photo by Andie Deroux.

Elayne Wiley and Danni Askini were and continue to be my mentors. We all are flawed humans; we all make mistakes as leaders; and we all will also do amazing things as leaders, hopefully. We touch people’s lives in ways we will never even know. Without that, I would not be the man I am today.

What has organizing security at Trans Pride Seattle been like? 

Security for the event has shifted over the years. We’ve always been concerned about security. We are a group that unfortunately will always need protection, and thinking otherwise would be naive.

Oliver Webb directs volunteers in setting up for Trans Pride Seattle (2022). Photo by Kenzie McMillan.

In 2019 specifically, there were threats that escalated across the country, thanks to Trump and MAGA [supporters]. That year, we saw a ridiculous amount of hate grow in this country, to the point that we needed to pivot our security to even higher levels. We had a 500-person wall that wrapped around a 25,000-person march. We had over 130 [security breach] attempts on the event, and none of them made it through—we stopped every single one. We had paid security, multiple local security teams, and volunteer security teams. We had to conduct very specific training to get all of these teams on the same page, and backup plans upon backup plans to make sure that everything was done safely and correctly so that everyone was protected. 

The next year, the [COVID] pandemic hit and we moved into an era where that hate escalated exponentially. We are now dealing with security issues that are constantly changing. As an organization that does not work with police, and works to uplift the BIPOC community and to be cognizant of the trauma that community has endured, and other marginalized and oppressed communities within our already marginalized and oppressed community, it is imperative that we do absolutely everything in our power to seek security options that will benefit absolutely all of us. 

Oliver Webb, WA State Senator Marko Liias, Stella Keating, and Danni Askini backstage at Trans Pride Seattle (2023). Photo by Alex Garland.

Every time I come into an event—and I secure many, many events all year round—I need to look at who’s going to be at this event. Who am I protecting? How am I going to protect them? What are the active threats? What are the possible threats? How do we do this in the best possible way? There are often many moving parts that [the public] does not know about.

We live in a very, very scary time, and putting on an event that is for the trans and gender diverse community—when we are being eradicated by our government—is scary. But we also can’t just go hide because people are being awful and trying to repeat history. It is our job as an organization—and it’s my job—to do everything in my power to keep TPS a safe and healthy event for everybody.

Accessibility and disability justice are really important to you. How else does that show up in your work with GJL? 

Oliver Webb with service dog Murphy at the Gender Justice Awards (2018).

It is a massive part of my life. I am an accessibility advocate. I do this in court. I do this all the time in my life. I do housing accessibility as well as general accessibility.

As GJL’s Accessibility Coordinator, I did everything from making sure (when we had an office) that our office was accessible, programs were accessible, and each event was accessible. I would go do site visits before we did events to make sure that we were picking accessible locations. 

For Trans Pride Seattle, I oversee the accessibility team, including organizing our Spoons Tent. We have worked very hard to figure out the best way to angle and soundproof our Spoons Tent every year. I physically go to every site and take pictures and measurements, and send them to our teams so that they know exactly how big the area is, if/how a wheelchair can fit, where there are any spots someone could fall or places an accessibility device could get caught on. I also work with our lighting and security teams—I have a hand in just about everything. I make sure that from the beginning to the end of the event, we know of anything that could potentially cause problems, so they can be dealt with. 

What do you feel most proud of in your work with GJL? 

There’s this picture of me taken by Alex Garland at my first Trans Pride Seattle—this amazing picture of me and my service dog coming in under [the TPS] banner. It’s one of the first Trans Pride pictures I have of myself. I look like such a baby trans boy. I saw this picture again recently and I teared up. I was thinking about the fact that it’s been seven years, and this is my sixth Trans Pride Seattle. I am proud of the fact that I have been part of something that continues to serve this community, regardless of the fact that each and every year we are attacked. Not at the event itself—but every single year something happens. Every year our permits are messed with or held up. Whether we try and plan from the day we end Trans Pride the year before—or we have huge plans with committees—no matter what we do, something will happen to make it hard for us to get this event off the ground. 

Oliver Webb is honored on stage at Trans Pride Seattle by the Sisters of Perpetual Indulgence alongside Danni Askini and Elayne Wylie (2022). Photo by Alex Garland.

For the past seven years that I have worked on this event, I have worked with amazing teams that have gone out of their way to get this event off the ground. That is the reason that I come back year after year. That is the reason I came back while running another organization last year, when we were down to a small handful of organizers showing up.

I’m sure to everybody else it feels like things are falling apart, and most days it feels to us like it’s falling apart, too—like we’re doing everything—but that’s what nonprofit life and volunteering is like, right? We all have to do a lot of emotional labor because we are a minority group. We should not have to do this, but the reality is that we do, so we do it. 

At the end of the day, Trans Pride Seattle needs to happen because we need a safe space for our community. I came back because we need this event. We have to stand up to society and say ‘We’re still here, and you aren’t going to eradicate us’. This event is something I’m proud of each and every year because no matter how hard it is to put on, no matter how much sleep I lose, and no matter how stressful it is to get off the ground, at the end of the day, it is necessary to the people who come to it, and it’s necessary to me. It’s my event too. 

Last year was a beautiful event. It felt romantic. It felt safe. It felt different than years past. It felt like a new event, and we pulled it off on hopes and dreams after an entire city tried to stop that from happening. It is something I am honored and proud to be part of, and no matter what happens, I am happy that I have decided to put my time and energy into it—because people need and want this event.

Attendees at Trans Pride Seattle talk to DAPS organizers at their booth (2022). Photo by Kenzie McMillan.

We do amazing things, and it’s really hard for any of us to take a minute and acknowledge and savor it because we’re probably on to the next thing already. We’re trying to fight for our communities, or put on the next event. We are so busy focusing on serving the people that we love and care about. We’re so busy trying to protect our future that we don’t have time [to reflect]. 

All I think about every day is making sure that my community is taken care of and that we make it to the next day. 

How else has GJL made an impact for trans and gender diverse people across the state and nationally?

GJL does a ridiculous amount of work and has for many, many years. Obviously, COVID has made it very difficult for GJL—and all of our organizations—to continue the majority of our work. We’ve had to pivot.

Senator Kuderer and Oliver Webb at Trans Advocacy Day (2023). Photo by Vlada Knowlton.

We’re still running the SafeHouse program serving trans & gender diverse survivors. We worked with Planned Parenthood to organize a Trans Advocacy Day at the Capitol in Olympia. We brought people to talk to representatives, encouraging them to back legislation in support of our communities. We’ve helped pass a lot of legislation.

We’re also shifting our work to become more national in scope. We’ve brought on national board members and are hoping to expand GJL into other states, especially states with anti-trans laws being passed. We are a sanctuary state here in Washington, and we are working to help pass additional shield laws across the country. We’re also working with organizers and people in other states to help trans people fleeing to our sanctuary state—especially BIPOC individuals with less access to the resources needed to relocate.

Oliver Webb, Stella Keating, Elayne Wylie, and Danni Askini at the Capitol during Trans Advocacy Day (2023). Photo by Lisa Keating.

What would you like to see GJL do in the next 10 years?

I’m excited about our national expansion, to continue to assist people in other states and to learn and grow from their partnerships as well. It will be fantastic to gain more perspectives from people with different levels of privilege. I’ve lived [in WA State] my whole life. I have no idea what it feels like to live in a state where I can’t go to the bathroom, where I can’t play sports, where my teachers will call my parents and out me, and then my parents will go to jail for giving me gender-affirming care. I’m very excited for our future as an organization to better serve the people we are serving because we will now have those perspectives on our board.

I also think making sure we appreciate the people who help us is important. I think that a lot of times we get bogged down by the amount of labor—and emotional labor—we’re all doing, but continuing to build our volunteer program and working to better express our appreciation for our volunteers is something that I am really passionate about as well.

Do you have a favorite or funny memory from your time with GJL? 

We, unfortunately, lost one of our former board members recently, chip Phillips, who was also a friend of mine. chip used to do facilities for Trans Pride Seattle. 

In 2018, when we used Cal Anderson park for TPS, our tabling fair would be on the astroturf field. After security checked the park for any issues, facilities volunteers would set up all the tents for the tabling fair. chip had spent who knows how long putting up all of these dozens of tents. All of a sudden, a gust of wind hit the field, and in unison, all of the tents lifted. And left. 

Luckily, Cal Anderson Park is surrounded by fencing on all sides, but all of those tents left their spots and moved. (laughing) I’m pretty sure I started filming it. chip left—like, anger quit. They came back eventually. It’s like when your friend falls and you know you shouldn’t laugh, and you are just laughing so hard. You need to pick them up, but you just instinctually laugh because there’s nothing you can do. I’m not gonna go catch a tent! Even if I caught one, I can’t catch 50! So, just FYI: you are to put four weights on the bottom of those tents at all times. You need to weigh them down or they become sails. 

It is hands down my favorite story, and it always has been, long before we lost chip. I am very, very happy it’s my favorite one because one of my friends will always be tied to my favorite story.

After chip’s Memorial, I turned on my GPS and it sent me the wrong way and rode me around the block, and left me right in front of Cal Anderson. I was forced to stop right where it happened. chip’s memorial was a block away from Cal Anderson Park, where all of the Trans Prides chip had ever been part of were. 

What other forms does your community work take nowadays?

Oliver Webb speaks on stage at Trans Pride Seattle on behalf of Diversity Alliance of the Puget Sound, alongside fellow DAPS member & TPS Medical Lead, Fran (2023). Photo by Andie Deroux.

In addition to my work with GJL, I’m also the Executive Director of Diversity Alliance of the Puget Sound (DAPS): a nonprofit working to support trans and gender diverse adults with support groups, advocacy, and financial aid. I’m also an accessibility and housing advocate, primarily assisting community members in court proceedings, during eviction processes, and in navigating rental issues. Since 2019, I’ve also run an all-volunteer security team that secures several pride events and other LGBTQIA+ events throughout the year. 

I am constantly volunteering, taking calls, and participating in coalitions. I helped start the Trans in Jail Coalition, which worked to get rid of the antiquated system of deadnaming people in jails despite them having had legal name changes. We also worked to get gender-affirming clothing and HRT for folks in jails. As abolitionists, our true end goal was to get rid of jails, but until we can fully do that, we need to take care of the people that are being harmed in this racist institution.

You’re also one of the key organizers for the local Trans Day of Remembrance events! 

Oliver Webb speaks at a TDOR event (2019).

DAPS also hosts Trans Day of Remembrance (TDOR) events annually for Tacoma and Seattle, both in-person and virtually. Last year we decided that we didn’t want to have these be trauma-bonding events anymore. We [trans people] only get two days a year that we are even acknowledged as a group of people: TDOR, where we name the trans people murdered that year, and Trans Day of Visibility, where we beg people to acknowledge that we exist, and do a whole lot of emotional labor educating people.

Last year on TDOR, we decided to start doing more of a roundtable discussion, bringing in a few panels of amazing trans professionals and a couple of allies who work very closely in the community, to discuss some specific topics such as domestic violence, medical systems, the racist prison industrial complex, and finding trans joy within trans families amidst what’s happening to our community. We didn’t want it to just be a time that we come together and be sad. Instead, we wanted to discuss how we take action, what we’re doing, and how we move forward.

Oliver Webb speaks on a panel at a TDOR event (2019).

Unfortunately, the following Sunday was the [Colorado Springs] shooting. We chose as an organization to still hold space for our community. Astro Pittman—founder of TDOR Seattle, a DAPS board member, and long-time organizer of TDOR events—and I explained why we were still choosing to hold our TDOR events. We scrapped all of the discussions and brought everyone together who had still shown up as speakers—leaders in our community—and they decided to discuss how our leaders were going to move forward after this tragic event. I put myself on the front line by leading security that day as well. 

What words of wisdom or advice do you have for people who are thinking about getting into organizing/volunteer work, especially in service to trans communities?

Oliver Webb speaks at a Trans Kids Rally (2023). Photo by Rowan Duran.

Just do it. It is not as scary as it seems. I think that lots of people feel like you have to be in charge, or be a leader, or have some sort of experience. That is not true. You can just be a volunteer. You can just email someone. Email Kai [Aprill-Tomlin]. Email me. Just reach out and say ‘Hey, I would like to volunteer,’ even if you only have half an hour a month. Whatever it is, someone will find something for you.

I used to do data entry for a shelter. I have done all sorts of different volunteering. If you can only do a small amount, just let people know. If you want to get involved, you can get involved in whatever capacity you want to be involved in. There’s no right or wrong way to be involved. I think that people get in their head thinking they have to be on stage, speaking; running a whole event—and that’s not true. You don’t have to be doing everything. If you are privileged enough that you are able to give financially, that is always a great way to assist, too—especially for allies. 

Any last thoughts?

I will continue to fight for GJL and TPS as long as others are fighting for it—because people love this community. GJL and the other people behind TPS love this community. At a time when we desperately needed it, Danni Askini came back to lead the organization and is doing so on the other side of the country. People said ‘We’re not letting this die’. That is an event I want to be part of. That’s an organization I want to be part of.