True Compass - Edward M. Kennedy

Going Back to My Roots

May 10, 2025

We are six months out from the great democratic experiment we call the United States of America being overrun by the Trump Regime. What are we doing to fight back?

Last week I was unable to write my Substack because I needed to jump on a plane to go back home to Boston. My dad needed surgery. All went well, but I'm now "down" the Cape tending to his recovery. It was quite a journey getting him home from the hospital in Boston to his home down the Cape—but we made it through the Friday traffic and over the bridge. I always find a sense of peace coming over the Sagamore Bridge, breathing in the salt air. After I was able to get my dad settled in for the night, I noticed a book on the shelf—True Compass: Edward M. Kennedy, A Memoir. Hmm, I haven't read this one yet. So off to bed I went, tired from the whirlwind of the last three days, armed with some bedtime reading.

While I've followed Senator Kennedy's career closely, and yes, I'm a big believer in his work and a true Kennedy fan - I hadn't yet read his personal memoir. I felt like the universe was telling me something: being back home during this moment when democracy hangs in the balance, knowing the pivotal role the Kennedy family played in shaping our Democratic party, and caring for my dad who exposed me to the historical significance of the Fitzgerald-Kennedy Boston legacy. There's something deeply connected to the moment we're in. Our democracy is being tested, and we have some hard questions we need to be asking ourselves.

I would have to say my love for politics and my connection to my roots comes from my dad. I remember very clearly when I turned 18 years old and became eligible to vote. It was April of my senior year in high school. I was sitting in the auditorium for one of those spring assemblies that places the fear of God in you for drinking and driving. If you're a Gen Xer, you can relate. I reached into my bag to see if I had completed my history homework—senioritis was definitely kicking in as I recall. I pulled out a card—hmm, "what's this?" It was a birthday card from my dad. Along with his birthday wishes came his instructions about making sure I stopped by the town hall on my way home to register to vote. His final instruction: "and don't forget you are a 'Democrat'"—Yup, got it—loud and clear!

My first exposure to the Kennedy clan was when I was about 9 years old. I visited the birthplace of John F. Kennedy on Beale Street in Brookline, MA, and then their second home in Brookline because they outgrew their first one. Senator Kennedy, aka Teddy, their 9th and final child, was born in St. Margaret's Hospital in Dorchester. The family had moved to New York for a stint, but Rose Kennedy insisted all her children would be born in Boston. Over the years, there were several trips to the JFK Library in Boston, and most recently to the Edward M. Kennedy Institute for the United States Senate.

One of Senator Kennedy's core beliefs, taken from religious teachings from his mother, Rose Fitzgerald Kennedy, comes from, as Senator Kennedy recalls:

"The great Gospel of Matthew, chapter 25—in which he calls us to care for the least of these among us, and feed the hungry, clothe the naked and give drink to the thirsty, welcome the stranger, visit the imprisoned. It's enormously significant to me that the only description in the Bible about salvation is tied to one's willingness to act on behalf of one's fellow human beings."

I find it profoundly troubling that the MAGA GOP claims to be guided by such religious teachings and yet during the first 100 days of the Trump Regime, they have done nothing but the opposite. The Trump administration's current proposed budget cuts to social programs such as food stamps (SNAP), housing assistance, and education initiatives would disproportionately harm low-income families, children, and marginalized communities. These cuts would exacerbate hunger, homelessness, and poverty, directly contradicting the call to feed the hungry and clothe the naked.

Additionally, the Trump regime's rollback of environmental regulations and withdrawal from international climate agreements will have devastating consequences for vulnerable populations, including low-income communities and communities of color, who are already disproportionately affected by environmental pollution and climate change. This move ignores the imperative to care for the least among us and protect the most vulnerable from harm. Where is the compassion? We need to keep reminding the American people who the MAGA GOP really are.

I'm about 100 pages into Senator Kennedy's memoir. During my time down the Cape, I'm going to take you along my journey reading his memoirs. Who was Senator Ted Kennedy? He was what many referred to as the Soul of the Democratic Party and the Lion of the Senate. A man who penned more than 300 laws himself - laws that changed the course of history. Why bring you along this journey? History teaches us many lessons, and the Democratic party right now is at a major crossroads. And like many of you - we're searching for answers, searching for direction. Yet, what's bubbling up in me is that the answers are right in front of us, but are we going to make the bold moves necessary to create the changes we want to see in our communities?

The opening of his memoirs features the first weeks of Senator Kennedy learning and understanding his diagnosis—glioblastoma, a severe and aggressive brain cancer. It was May of 2008 when he first learned the news. As he was processing his diagnosis and attending to his health, he was quietly hoping to be able to attend the Democratic National Convention in August—one more speech—one more hurrah. With an entourage of doctors accompanying him to Denver, Senator Kennedy was able to walk onto the stage and deliver his final convention speech and introduce Barack Obama as the Democratic Nominee for the 2008 Presidential election.

"There is a new wave of change all around us, and if we set our true compass, we will reach our destination—not merely victory for our party, but renewal for our nation. And this November, the torch will be passed again to a new generation of Americans." ~ Senator Ted Kennedy

They say history has a funny way of repeating itself. The nation and the Democratic party are again at an inflection point. Currently, Democratic party - a duel between the old and the new. If we want to rise to this moment, it's time to lay out our plans; our true compass. We know what needs to be done—yet why the hesitation? While steps are being made—it's time for bold initiatives! And full transparency.

As a young boy, Teddy was not perfect, and as the youngest of nine, he seemed to like pushing the envelope a bit. Yet, Rose Kennedy would not let anything slide. Off to the closet for a time out and some time to think about his infractions. One time while in the dark closet, feeling sorry for himself for missing out on all the action on the other side of the door, he suddenly realized he wasn't alone in the dark. His sister Jean was in the closet too for some infraction—instructed to ponder her missteps as well. Together they made it through their punishment. The lesson? We do not have to search for the answers and solutions alone or in the dark. Reach out and make connections with each other.

Bold Ask

Have you been DM'ing and chatting with others on Substack? Great, keep doing it—and I challenge you to take the next step and schedule a 30-minute Zoom coffee chat this week. Reach out, connect, learn what is going on in another state. Ideate, live in possibility. Don't feel like you're sitting in the dark alone—there are many of us out here working to restore our democracy.

Our True Compass

If we want to course correct and get out of this dire situation we're in—we need to focus our efforts on 4 distinct pillars—our True Compass:

Run candidates in Every Single District—up and down the ballot.
Build a media ecosystem that allows our message, values, and solutions to reach voters.
Stop going from boom to bust with our organizing efforts.
Really lean into leadership development.

Our True Compass: Gloves Off Time

I'm going to be honest here—gloves off time. The more we can show up and have authentic conversations with ourselves, the quicker we'll move to enacting solutions.

When I read Senator Kennedy's story about being in the dark closet with his sister Jean, I not only laughed—I related. I feel like we're walking around in the dark not reaching out to what is directly in front of us. We know exactly how we got here.

1) REDMAP: The GOP's Master Plan We Must Reverse

The GOP implemented a masterful plan, and we can reverse this by running candidates in every single district up and down the ballot. We focused too much on federal elections; we ignored the power grab happening at the state and local levels. Now, don't get me wrong, the success of an organization is based on a clearly defined mission, but we have not been equally funding and supporting organizations focused on state and local power.

Why Voter Turnout is the Real Victory

Elections are not just about winning—it's about maximizing voter turnout! When we run candidates everywhere, we give every voter a reason to show up, regardless of whether that district is "winnable" in the short term.

2) Building Our Media Ecosystem

While the GOP has funded and cultivated a well-oiled media complex, Democrats were asleep at the wheel despite warning signs and people like

Tara McGowan

waving the warning flag back in 2020 and earlier. As a result, disinformation has become its own beast, blocking many candidates' ability to penetrate with a clear Democratic message because FOX News (I say that loosely) fills the void of the many news deserts spanning across this country.

Will Robinson

dives into why we need a reboot!

We need to invest in local news, content creators, and media outlets that can reach voters where they are—not where we wish they were.

3) Breaking the Boom-to-Bust Organizing Cycle

Dakota Hall

explains this best. I have watched this happen time and time again at the county party level.

“Progressive politics loves a buzzword. We cycle through them—"relational organizing," "digital mobilization," "distributed everything"—as fast as they trend on X. The problem isn't catchy language; it's what gets lost inside the slogan. When a group brags that it "organized 10,000 people on Saturday," odds are they didn't organize at all. They mobilized a pre-existing list for a one-off action.

“Treating those two verbs as interchangeable isn't just sloppy copy; it's a strategic blind spot. We end up pouring resources into turnout spikes that evaporate by Monday and starving the slower, sturdier work that actually shifts power”.

4) Leadership Development: The Foundation of Everything

As a party and a movement, we need to be leaning heavily into leadership development.

Amanda Litman

is leading the way. How do we lead differently, creating space for new leadership and thus new goals? When We Are In Charge, the Next Generation’s Guide to Leadership - coming out on Tuesday - provides a playbook to help us navigate the moment we're in.

At the core of any successful organization or movement is leadership! Full Stop. 🎤

This is our True Compass—the four pillars that will guide us back to not just winning elections, but rebuilding the structures of democracy that have been systematically dismantled. ~ its not complicated!

The Courage to Transform

We need the strength and fortitude to make some tough decisions over the next few months—decisions that might alienate some and excite others. We as a party in this moment, in this fight for democracy, are being called upon to create a future that otherwise would not exist unless we make it happen.

We need to remove real or perceived constraints—we need to shift them to create new possibilities from a place of nothing. We need to see the future and generate new possibilities under any circumstance. We need to challenge ourselves to put the past in the past, letting go of old patterns of thoughts, beliefs, values, fears, and habits that no longer serve the Democratic party.

Closing Thoughts as We Head Into the Weekend

Senator Ted Kennedy passed away at his home in Hyannis Port, Massachusetts, on August 25, 2009. I remember as clear as day when I heard the news that Senator Kennedy was no longer with us. And again, a few days later, I recall exactly where I was when three generations of Kennedys followed Senator Kennedy's flag-draped coffin from Hyannis Port en route to the JFK Library in Boston.

A black column of limousines slowly made their way into Boston after a private family mass at their home. Thousands of mourners lined the 3-hour route. At the time, I was living in Cohasset, a seaside town in between the Cape and Boston. It was announced on the news that the private mass had ended and it was time for Senator Kennedy to make his final journey to Boston.

Without thinking twice, and with tears in my eyes and a heavy heart, I grabbed my car keys and drove up to Route 228 to where the motorcade would pass—there was only one route from the Cape into Boston—a two-lane divided highway—Route 3. Within 20 minutes I arrived on the northbound side. I pulled my car over, as did all of the cars. I could sense the motorcade was soon to arrive because there was not a single car on the highway—it was surreal.

I got out of the car and stood on the side of the road with hundreds of other mourners. When the motorcade was in sight, we locked hands without hesitation, reaching out to the stranger next to us, lowered our heads, and stood in silence. It was the purest moment of humanity that I had experienced in a long time.

There was an unspoken deep sense of respect, an appreciation of a lifetime of work, of sacrifice, of commitment to the collective good. Senator Kennedy was a true servant to the people. While he was not perfect by any means, he fought for the people. He had a mindset that allowed him to fall forward—learn from one's mistakes because defeat was not an option.

Some have critiqued the "Kennedy" mindset over the years, but if we are going to save our democracy, we better shift our thinking and adopt a new way of doing business—a new mindset.

More to come over the next few weeks as I walk the seaside landscape of Cape Cod—deep in thought about our past and our yet undefined future.