Shaped By Political Inaction And A Failed System

Tim Cywinski’s understanding of politics didn’t start in a classroom or a campaign. It started in his own family — when his parents were forced to choose between paying for their son’s medical care and keeping their home.

Tim’s brother was born with a serious heart condition. Insurance companies initially refused to cover the care, calling it a “pre-existing condition” — a label used to deny coverage and put families in impossible situations. Tim’s mother — now an educator, but a lawyer at the time — pushed back and forced the insurance company to provide coverage.

But even with coverage, the bills piled up. The choice became pay the medical expenses or afford the mortgage.

Tim’s family was fortunate to recover. Many families aren’t.

His viewpoints aren’t from textbook case studies on healthcare. They’re from early exposure to a failed system.

From Politics to Real Life and Back Again

Tim first got involved in politics as an intern on the Obama for America campaign in 2008, and continued working on electoral campaigns through 2011. It was where he saw the promise of what politics could be — and the gap between that promise and how it actually works.

Then he stepped away from politics — and into real life.

Tim started at community college, working two full-time jobs while taking classes — often seven days a week. When he transferred to complete his undergraduate degree, he continued working two jobs while earning a degree in Political Science, with a minor in International Relations.

Doing the Work — Inside and Outside Government

For more than a decade, Tim has worked to change how our politics delivers for people.

He’s worked inside government — including time in the U.S. Senate — and outside of it through non-profit and non-partisan advocacy. He did community organizing with the National Education Association before moving to Richmond to work as a lobbyist for a small, youth-led organization focused on college affordability, campus safety, and economic fairness for future generations.

Today, he serves as Communications Director for the Sierra Club Virginia Chapter, working with communities across the Commonwealth to take on powerful interests and prove that people can be their own champions.

A Track Record of Delivering Results

Tim’s work isn’t theoretical — it’s grounded in real results for real people.

• Helped secure $100+ million in increased financial aid for in-state students — and stopped efforts to cut it

• Strengthened campus safety and expanded access to technical training opportunities for young people

• Trained grassroots leaders to advocate for Medicaid expansion in Virginia

• Supported efforts to pass the Virginia Clean Economy Act and the Environmental Justice Act

• Helped communities fight back against pipelines, toxic energy projects, and polluting facilities across the Commonwealth

• Authored a statewide report exposing disproportionate impacts of air pollution in vulnerable communities

• Stood with rural communities to fight the largest proposed private landfill in the country

• Organized with residents to stop massive data center developments in multiple Virginia communities

Time and again, communities were told they didn’t have the power to win.

Time and again, they proved that wrong.

Why He’s Running: Reform the Rules

What Tim has seen — what moves, what stalls, and who gets left out — is why he’s running as a reformist.

The problem isn’t a lack of good ideas. It’s that the rules of our politics were written to protect the powerful. Until we change them, we’ll keep falling short, no matter how strong our policies are.

A Fair Shot For Everyone. No Exceptions.

That’s why Tim is running on the Fair Shot Agenda: to reform the rules, restore real representation, and build an economy that works for the people who don’t have lobbyists.

This campaign is for the families who are doing everything right — working hard, contributing to their communities — and still feel like they’re falling behind.

And it’s built on a simple belief: We don’t have to settle for politics that works this way. We can expect more. We can change it.