The direct aid organization Operation Lifeboat is looking for volunteers in case management for its mission helping Trans Kansans get to safety in the wake of the state’s landmark legislation making trans people undocumented overnight. To better understand that mission, I spoke to one of the core members of Operation Lifeboat’s team: Vasilios Rosenzweig.
Vasilios, a Chicago native and Operation Lifeboat’s Deputy Section Planning Chief, sat down with me to explain his work.
The interview has been edited for length and clarity.
I started by asking him to paint a picture of his native Chicago. He said that he’s been “able to experience Chicago's entire spectrum of living and working, which has been really insightful for me. So through that, and through some of my own activism, I've been able to see that Chicago can be both stubborn and very progressive at the same time, depending on who you're talking to.”
He also said that “most of all, [Chicago is] resilient and strong”, and discussed the city’s reaction to ICE’s Operation Midway Blitz.
“Generally speaking Chicago is a place of inspiration and hope.” - Vasilios
“When ICE came to Chicago en masse, there was a lot of speculation of how Chicago would handle it. We have been great at being nonviolent, protesting peacefully while continuing everyday work, everyday life's job and everything that everyone does while also contributing to basically making sure that our neighbors have a better tomorrow.”
Vasilios illuminated what it’s like to be in Chicago.
“I'm really proud to be here. I actually have opportunities that could take me away from here, but I'm resisting and staying here because the community here and the people here, they're friendly, they care. Most people here tend to care about whatever they're doing. There's not a lot of apathy here.
No matter who you're talking to, someone cares about something.
There are a lot of resources because Chicago is in this vast area, but it's smaller than it may seem. It takes on so much geography, but it's all kind of densely packed into areas, into neighborhoods, and they each have their own heart beat. While I am not an active member of the community, having spoken to organizations and being boots on ground here as it pertains to our emotional life, I know that there's a lot of support internally at the best or underground. There are a lot of people here that feel like they can choose to be who they are.”
From there we moved on to Operation Lifeboat. I wanted to know what the Operation did, in his own words.
Can you describe to me Operation Lifeboat in your own words? I’m going to open the floor to you on that:
“Operation Lifeboat is a group of people that don't know how to set things down, and are constantly looking for ways to support people in need.
This group came together when Samantha Boucher reached out, knowing that there was an imminent threat with SB 244 and what it could mean for other states. Based on the group of people that we are, it wasn't a question of how or when or how long or how difficult. Everyone just said ‘yes and when do I start’.”
Vasilios also explained that when the operation first started, time and effort was spent “figuring out what we were doing in [this] space.” He stressed that the operation’s team at that time was careful to assess “what the response, the proper response was for such a delicate situation.”
He further explained that as the Operation has matured, it has “turned into a case management, non-profit organization spun off of Trans Liberty specifically helping those that have been affected by SB 244 in Kansas.”
While the focus is currently on Kansas due to its law that made trans people undocumented overnight, the plan to support trans people is broader. Vasiliso stated that “When it’s time to scale and answer the call in other states, we [will] have those resources to be able to spin it up.”
What does “boots on the ground” look like for you, and for what you've seen as part of Lifeboat:
“Boots on the ground? From my perspective I've had three experiences of that so far.
The first was a call to Topeka in Kansas when Samantha was performing civil disobedience. That was actually really interesting. We had a staff meeting on a Monday night, and immediately after that call, I hopped on a call with our Incident Commander going through some work.
Our safety officer, David Dodds, is also Chief Operations Officer for Trans Liberty, hopped on the call. He goes, ‘Hey, man, can you be in Kansas tomorrow?’ And I was like, ‘Sure.’
I hadn't gotten a lot of sleep that day, or that whole weekend. But going wasn’t a question. I left my office on two buses to get home and pack my things. I already had a go-bag prepared so I could be deployable anywhere within two hours.
I hopped in my car, and by 10pm I hit the road. Straight shot to Kansas. I arrived around 8:30am. Got about half an hour to an hour of sleep.
Those of us with Samantha went to the state capital in Topeka and performed the act of civil disobedience. Afterwards we enjoyed Waffle House.
So that was very powerful and moving for my role. I mostly just held the camera and made sure that we had enough media to document the events for the future.
I returned home to Chicago after that.
The second, and this is ongoing, is I’ve connected with an organization with a mission adjacent to Lifeboat– not case management but moreso assisting with relocation [after people move]. Continuing to maintain that relationship, help out where we can help them and vice versa, that's an ongoing effort.”
Continuing, Vasilios explained what that “ongoing effort” looks like.
“Third; a few weeks ago I was out in Seattle, and I was able to meet with some organizations, one of which we will be connecting with resources. In a few weeks, I'm going to be going to Washington [State] for a few months. The goal there is to connect with the right organizations.
Also, attending Lawrence Pride in Kansas– which I'm very proud of our team for– I was not in attendance for that. Many of our team members are connecting with organizations and getting our name out there, plus everything in between.”

I know that Operation Lifeboat has paused new requests for assistance. What does pivoting look like in this context?
“During this time, obviously, it's expensive to help people relocate. Legal services can get expensive. Someone’s bills and rent can definitely climb up there. Funding is a primary need of ours at this moment.
In the meantime, one of the things we made sure to do immediately once we assessed our position, and we reached a point where we felt like any new case that was coming on were at a risk of not being served at full capacity.
We've all seen cases where organizations will over promise and then their resources run dry. We made sure we weren't in a position where that was a possibility.
So we're handling our cases that are active right now, as if nothing changed, because as it pertains to them, nothing has. We're fulfilling their needs to the level they need.”
What's the single most important thing that trans people in ‘safer’ areas can do to help Lifeboat? And, what's the single most important thing that allies, regardless of area, can do right now to support Lifeboat and get the mission to where it needs to be?
“I think social media has made it really easy to feel like you've spread the word by sharing something. There's a gap.”
Vasilios continued, explaining that doing more than reposting something on social media is both necessary and sometimes frightening. The real work, in his view, is direct conversations with people.
He described how it feels unnatural and even sometimes scary to have those conversations with someone else. Vasilios alluded that the idea of trying to make that connection and invite someone into the work is hard.
Continuing on, Vasilios gave some examples of places where people can plug in to work with Operation Lifeboat or similar efforts.
‘I have a computer, which means I can help with virtual stuff. Maybe I can be a virtual case manager, or I can help with software stuff, finding resources, interviewing people, finance, whatever.’
‘Okay, you have a laptop, those are the things you can do which sound appealing to you?’ ‘Hey I have a spare room that never gets occupied, maybe someone can stay here for a few days, for a week, whatever.’ ‘Hey, I have a car’
I think listening to your gut and acting on it would be my strongest recommendation.
You said earlier that fear is not what this should be built on. What should it be built on?
“I think that trust goes a long way, which I know is counterintuitive, because who can you trust in a time when who knows who's watching, or who wants to act maliciously. Trust is what it should be built on.”
Is there anything that you feel like it's important for my audience to know about?
“I don't want this to come off in the wrong way, but I've managed to step into a lot of arenas in a very short amount of time, spanning from military, to big four accounting, to investment bankings, and now grassroots organizing. I've seen amazing leaders, amazing orgs, horrible leaders, horrible orgs, and everything in between.
This is the single best team I’ve ever been on, and the most honored I've ever felt to be part of a team in my life.
I’ve worked with people on the cover of Bloomberg, Wall Street Journal, The Times. I have worked at the largest accounting firm in the world, and boy I'll tell you about Operation Lifeboat. I'm gonna get emotional, it's like Avengers but in real life.
This is not a group of people that are just picking up a phone, figuring it out, and then moving on to the next thing. This is my life, and everything I can do to benefit and help, I'm going to do for as long as I can.
The people involved in Lifeboat don’t need to be doing this specific thing, running the Operation. They are anyways.
They are leaders, they're titans of their industries. At any given day they probably have 50 opportunities on the table for them with varying resources, scale of opportunity, and experience.
They have opportunities that can drive a resume forward, but that's not the interest here.
Again– these are superheroes that could be you know taking down Thanos but they're here on Earth.
I just want to shout out the team. I know it's commonplace to do so, but I really don't say it lightly. Every single team I've been a part of had some phenomenal people, but it doesn't even come close to the people with Lifeboat and Trans Liberty. I'm very honored and proud to be here.
I have no end date in mind. This is something I'm committed to for the next 40 years of my life. Everyone shares the sentiment of ‘I'm here and doing it’. I just want to shout out every single person on the team because there's sleepless nights, there's tears, literal blood sweat and tears. Maybe it's a little bit of a personal thing, but I'm very proud, and I appreciate being part of such an amazing team at such a young age.
These are the people that have proven it time and time again across the world and on a global front that they are going to lay it on the line.
If there's a team to root on, to vote for, it's us. We're going to do everything we can to make sure that every single person that needs help gets help to the best of our abilities. And our abilities are pretty great! So, trust in us.”
Vasilios also shared that people can get involved with the Operation Lifeboat team and help its mission.
“We’d love to have more volunteers. There's lots to do as we scale. There's things to do even now.
We could use case managers– you're going to get experience from case management that has worked in every capacity in the states out of the states so you'll get to refine case management skills you'll get to learn from leaders and and titans of their industries while doing an amazing thing for people that really, really, need our help.”
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Disclaimer: Jane and Artemis are also involved with Operation Lifeboat in a public information capacity. See more on the partnership HERE.
Operation Lifeboat is an initiative by trans people and our cis allies to get trans people to safe havens, on our own terms. They help with the logistics, organization, and money. Trans people are in charge of the course of the operation and their own destinations and definition of safety.
