John Masters, Author at Deep Something

A Polite Version of Josh Wostal Is Still Too Much

September 3, 2026 B. John 71 Views 0 Comments Stacy Hahn, Neil Manimala, developer contributions, Wostal, Ron DeSantis, Hillsborough County Commission, Hillsborough School Board, Campaign Finance

This entry is in the series 2026 Elections

Stacy Hahn doesn’t sound much like Josh Postal. She’s thoughtful, qualified, and generally pleasant. But votes count the same whether they come with a scowl or a smile, and Hahn’s eight years on the Hillsborough County School Board show a record that’s much more conservative than her polished image suggests.

Hahn opposed letting voters decide on more funding for teacher pay, voted against defending that referendum when Postal and the County Commission tried to block it, rejected a Pride Month proclamation, and publicly aligned herself with Ron DeSantis’s political group. There are some exceptions in her record, but when it comes to taxes, LGBTQ recognition, sexual-health education, and DeSantis-era politics, the pattern is clear.

Now Hahn is running for the County Commission with a campaign mostly funded by construction, development, real estate, and government-relations groups—including businesses that have worked with Hillsborough County. These contributions don’t prove improper influence, but voters have a right to look at who is supporting a candidate and what choices that candidate might make in office. Dr. Hahn may be a more pleasant version of Josh Postal, but the real question is whether Hillsborough County needs another version at all.

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Ambition, Attendance, and the Race for HCSB District 2

August 31, 2026 B. John 100 Views 0 Comments Public Education, Hillsborough County, Tampa Politics, Hillsborough School Board, District 2, Brittany Lyssy, Local Governance

This entry is in the series 2026 Elections

When someone wants to lead a multi-billion-dollar school district, authenticity comes first. Brittany Lyssy’s campaign for Hillsborough School Board District 2 asks voters to believe that a family of five lives in a 680-square-foot, one-bedroom condo while also keeping a homesteaded home in Manatee County. From barely attending advisory board meetings to repeating national talking points, District 2 voters deserve real community representation, not a staged political act.

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The Friends Who Walk With Us

August 30, 2026August 30, 2026 B. John 155 Views 1 Comment grief and friendship, human connection, Gratitude, Stoicism, Marcus Aurelius, Seneca, Friendship, sympatheia, lifelong friends

This entry is in the series Journey Through Stoicism

Some friendships stretch across decades. Others arrive for a season, bringing exactly what we need at the time. A little wisdom. A little laughter. A place to rest. A reminder of who we are when life gets noisy.

In The Friends Who Walk With Us, I reflect on the people who have shaped my life, from friends who knew me when I was young to newer friendships formed in this latest season of change. Some are still close. Some have drifted. Some are gone. Yet each left something behind.

The Stoics understood friendship as part of a good life. Seneca wrote about loyal friendship; Marcus Aurelius about our deep connection to one another. Over time, I’ve come to see that friendship does more than comfort us. It changes us. We carry forward the patience, courage, humor, kindness, and wisdom others once gave us.

And maybe that’s part of the quiet duty of friendship. To receive what others give us.

Legislature Featured Places Tampa Politics

When Tallahassee Called, Josie Tomkow Answered

August 27, 2026August 27, 2026 B. John 130 Views 0 Comments Senate District 14, Josie Tomkow, Tampa Politics, Home Rule, local control, Hillsborough County, Tallahassee preemption, party leadership

When Josie Tomkow had the chance to support local communities, she chose Tallahassee instead. This pattern appears throughout her House voting record: tenant protections, land use, infill development, vacation rentals, civilian oversight, worker rules, and school-board governance all go the same way.

This matters because Tomkow now wants to represent Senate District 14, which includes Tampa and Hillsborough County. But her record comes from somewhere else, and it raises an important question for voters here: when local needs clash with party leadership, whose side will she choose?

Her votes seem to answer. Even when another Hillsborough Republican voted no on a major preemption bill, Tomkow voted yes. So the question is not whether she can learn Tampa’s concerns. The question is whether she has already shown us who gets her vote when Tallahassee comes calling.

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The World Needed Dolly Parton

August 27, 2026 B. John 114 Views 0 Comments Dolly Parton, Imagination Library, philanthropy, LGBTQ equality, Legacy, Dollywood

Long before Dolly Parton became a superstar, I met her at a little outdoor music park near Kings Mountain. I am not even sure she was the headline act. It was a fleeting childhood encounter, but it connected me, however briefly, to a woman whose generosity would eventually touch millions of lives.

Dolly created jobs, helped students stay in school, supported families devastated by wildfires, funded research behind the Moderna COVID-19 vaccine, provided free college education to thousands of workers, and delivered more than 332 million books to children. She also stood firmly with the LGBTQ community, even when doing so cost her support among some fans.

Dolly Parton wrote songs the world will always remember. But the most beautiful thing she created may have been the life she chose to live. Read my tribute to a woman who proved that success means far more when you use it to lift others.

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Trump Wants the Midterms to Be About Trump

August 26, 2026 B. John 98 Views 0 Comments Republican incumbents, MAGA Inc., campaign advertising, voter accountability, Democratic politics, Donald Trump, Cost of Living, 2026 midterms

This entry is in the series 2026 Elections

Donald Trump has looked at a 34 percent approval rating and reached a comforting conclusion: Americans have not seen enough Donald Trump. His super PAC is preparing midterm ads built around his record, his speeches, and clips of Trump praising Trump. Apparently, the nation has suffered from a shortage.

The ads will tout stock-market highs, factory output, falling overdose deaths, and other signs of the “Golden Age.” Families will still see grocery bills that keep climbing, gasoline near $4.09 a gallon, and a job market that lost ground in July. The Dow Jones Industrial Average has yet to buy anyone’s groceries.

Trump wants voters to treat the midterms as though his name appears on every ballot. They should accept the invitation. Then they should ask every Republican incumbent whether Trump’s record belongs to them too, which votes lowered costs back home, and why the greatest economy in history remains so difficult for most people to find.

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When Home Changes Hands

August 25, 2026 B. John 143 Views 1 Comment Stoicism, home, Kings Mountain, grief, Family, Memory

This entry is in the series Journey Through Stoicism

Today, the house I called home for at least 62 years belongs to someone else. The deed has changed hands, yet the rooms still hold holidays, family gatherings, neighborhood friends, and snow days spent sledding down the street. Somewhere in my memory, the treehouse is still waiting in the backyard, and Mom is still inside making space for us.

Grief comes in pieces, and sometimes one of those pieces is a place. Selling the house feels like another small loss, arriving nearly a year after Mom’s death. The house still stands, but I can no longer return to it as home.

Some pieces came with me to Tampa, including Mom’s porch rocker and my grandfather’s mantel clock. The rest must live in memory now. “When Home Changes Hands” is about letting go of a place that helped form me and hoping the next family fills it with the same warmth, safety, and love that Mom gave us.

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What Is the Money For?

August 25, 2026 B. John 92 Views 0 Comments billionaire wealth, billionaire philanthropy, generosity, economic inequality, Jeff Bezos, Andrew Carnegie, public good, wealth and power, moral responsibility

This entry is in the series The Stoics

A single mother stops at a traffic light and hands five dollars to a homeless person. Jeff Bezos pledges $10 billion to fight climate change. Bezos will accomplish far more with his gift. Yet the mother may have given up something she needed.

That distinction sits at the heart of my latest essay. The world’s richest people possess more money than they could spend across several lifetimes. Their fortunes keep growing while the planet warms, public institutions weaken, and millions struggle to survive. Their philanthropy does useful work, though it rarely costs them any comfort or power.

So what is all the remaining money for? The answer takes us through the Gilded Age, the widow’s offering, other religious traditions, private bunkers, life extension, and the strange belief that enough wealth can free someone from the fate shared by every human being.

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Before We Choose Together

August 14, 2026August 14, 2026 B. John 161 Views 0 Comments special interests, representative government, Civic Engagement, Tampa Politics, Campaign Finance, political power, Democracy, voter influence, political access, community leadership

This entry is in the series 2026 Elections

We like to tell ourselves a comforting story about democracy: everyone gets one vote. The developer who can spend thousands on campaigns gets one. The teacher gets one. The restaurant worker gets one. The college student voting for the first time gets one. On Election Day, at least, the arithmetic is wonderfully simple.

But political power starts working long before Election Day. Candidates need money, introductions, endorsements, volunteers, organizations to support them, and people who can get them into the rooms where political relationships are built. By the time most voters start paying attention, a much smaller group may have already spent months deciding which candidates have the money, visibility, and standing to be taken seriously.

That raises a question I hadn’t fully considered when I wrote What We Choose Together: What needs to happen before the word “together” is really true? In Before We Choose Together, I look at money, access, community ties, and the kind of public officials who still answer the phone and talk with regular people. Our vote matters, but so does our ability to be heard before we cast it.

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Mike Suarez Knows Insurance. That’s Why I Have Questions.

August 7, 2026August 7, 2026 B. John 261 Views 0 Comments PACs, Mike Suarez, Campaign Finance, Insurance, Florida House District 64, homeowners insurance, auto insurance, Luis Salazar

This entry is in the series 2026 Elections

This entry is in the series Florida Legislature

Mike Suarez says his 30 years in insurance make him the best candidate to tackle Florida’s insurance crisis. With what homeowners and drivers are paying, that sounds like valuable experience. But his campaign finance reports show something else voters should think about: insurance-related interests are also the largest industry group I identified among his contributors.

That doesn’t mean anyone bought Mike Suarez’s vote. But it does mean voters have every right to ask a tougher question. If you’ve worked in an industry for decades and people connected to it give a lot to your campaign, whose interests will matter most when insurers and policyholders want different things?

Suarez wants voters to see his insurance career as a reason to elect him. That’s fair. But his professional and financial ties to that same industry deserve scrutiny too. Florida families don’t need another explanation for high insurance costs. They need someone in Tallahassee who will tell them exactly how their homeowners and auto insurance bills will go down.

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A Softer Kind of Courage

August 4, 2026 B. John 189 Views 0 Comments control, Courage, emotional strength, inner calm, Stoicism, Resilience, Acceptance, Temperance, uncertainty

This entry is in the series Journey Through Stoicism

What if strength does not always look like pushing harder?

In this new essay, I reflect on the habit of staying busy when financial pressure, uncertainty, and professional pride start to feel heavy. Being active can help us move forward, but it can also keep us from facing what’s already there. A surprising lesson from the human lungs opened another way of thinking about courage, one built around softness, space, and the wisdom to release what we can’t control.

The Stoics never asked us to become rigid. They asked us to see clearly, act where we can, and stop exhausting ourselves against what will not move. A Softer Kind of Courage is about learning when effort serves us, when it becomes avoidance, and why sometimes the bravest thing we can do is pause long enough to breathe.

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