Weekly Letter: Not Working

Sign up to receive County Executive Pittman's Weekly Letter to be the first to learn about big announcements, and get an inside look at issues crossing the County Executive's desk.


I try to stick to happenings of the week in these letters, and I enjoy telling it like it actually is. The truth is that last week I didn’t work. Well, I mostly didn’t work. There’s always writing this weekly letter, responding to emails, and jumping on a few important calls, but my kids had a week off and we went on a road trip, south.

We did two nights at Great Wolf Lodge in Williamsburg, where we combined crazy water slides with immersing ourselves in colonial history. Then we drove to the Outer Banks, saw the Wright Brothers National Memorial, collected sea shells, took the ferry to Ocracoke and back, and generally just enjoyed forcing 14-year-old twin boys to interact with their parents by sharing a hotel room, walking together, and driving a lot. 

On the way home we drove up the Virginia and Maryland Eastern Shore and spent the last night in Salisbury. I’d never spent any time there, and knowing former Mayor Jake Day, I had to see what he was so damn proud of. He turned us on to a great restaurant, great ice cream, and a great little zoo. Fun town.

The best part of being “off” or “away” to me is shifting mental gears. To help with that, I read two books. First was one that Mayor Gavin Buckley gave me at the recent ceremony announcing the purchase of the Moore property near Carr’s Beach. It’s They Call Me Little Willie, by Mark Cheshire, and it’s about Willie Adams, the numbers runner turned real estate mogul from Baltimore who created the best Black entertainment venues in the area, including Carr’s Beach. 

It’s a fascinating story that starts with a Black boy in North Carolina whose mother made sure he learned math so he wouldn’t be taken advantage of in business like his sharecropper father had been. He moved north to Baltimore in 1929 at age sixteen, got a job fixing bicycles, and then figured out how to run the depression-era version of the lottery, when it was illegal but everywhere. Willie later became a one-man minority business enterprise program, lending money and doing partnerships wherever he could find Black talent with an entrepreneurial drive. The city’s white political establishment loved or hated him, depending on whether he was making them money, and the ones who hated him kept trying to put him in jail. They figured he must be a mobster criminal, but most of his later business ventures were legal, and his empire was never built on violence. It was built on generosity. They need to make the movie.

The other book was Heather Cox Richardson’s new Democracy Awakening. She’s a historian whose daily “Letters from an American” I read every morning. The book describes the creation of our country’s democracy and the threats faced by it today, but then reminds us of the major shifts in the country’s political alignments through the years. She describes the moments in history when people came together and expanded rights and opportunity for groups that had previously been shut out - Emancipation, New Deal, Civil Rights and War on Poverty - and how democracy was challenged in response to each. It ends with optimism. We The People have done this before and emerged better each time. We can do it again. 

But I’ll tell you the coolest thing I did on this vacation. Before we left, my wife Erin was rummaging in the basement and came across a box with letters from my siblings, parents, and girlfriends to my eighteen, nineteen, and twenty-year-old self, and a couple of travel diaries I’d done. I read every word. The best was my detailed account of the summer after high school when I decided to go check out the world to prove to myself I could deal with it, so I hitch-hiked from Maryland to Los Angeles and up the west coast to Humboldt County, California where I got work on a dairy farm to pay for a Greyhound ticket to get me home just in time to enroll at University of Chicago. I’ll save those stories for the tell-all book when I’m no longer in office, but reading about it sure did remind me what it was like to be eighteen. That was a trip.

It felt good to drive back across the Bay Bridge and see the sign welcoming us to Anne Arundel County, The Best Place - For All. Of course, my crack team on the fourth floor was knocking stuff out of the park without me, and it’s been a very good week back home. 

I’ll tell you all about it, next week…

Steuart Pittman
Anne Arundel County Executive