Welcome back to Riders Up! The 152nd Run for the Roses and my 28th year stepping into a puzzle that has humbled even the sharpest racing minds. Every so often, it gives something back. Last year was one of those moments. Sovereignty delivered, and my top seven selections all finished in the top eight, with eight in the top ten. That’s the kind of result you appreciate more than you explain. Preparation meets providence.
This tradition has evolved. What started as handicapping has become an annual personal checkpoint. A moment to reflect on what actually matters. God remains at the center, guiding both the seen and unseen. The Derby is the backdrop, but the real story is everything that has unfolded between last May and now. So before the gates open beneath the Twin Spires, I pause, give thanks, and get ready to chase greatness once again.
This Derby Day also marks a personal milestone, two years since Denise and I had our first date. We don’t miss a month, so yes, that makes this our 24-monthaversary. Not a bad return on a Bumble swipe, especially with God writing the script.
Quick birthday shoutouts to my brother Jason's better half, Jess, likely wearing the best Derby hat in the room. Also a belated 50th to my sister Tracy's husband, another Jeff, who is most likely lining up an eagle putt as we speak.
Wow! What a year. Denise and I were married on July 7th beneath the grandeur of San Francisco City Hall. Just the two of us, joined by our Pastor Greg Hendricks—fresh off him being named Chicago Bears Chaplain and certainly playing a role with their incredible turnaround—standing before God and stepping into covenant. No guest list politics. No seating charts. No plus ones. Just us, God, and a commitment that carries a bit more weight than a Pick 6 ticket.
We celebrated our wedding evening in Yountville at The French Laundry, seated outside on a perfect Napa night just a few doors from where we had our first date. Denise had been waiting her entire life to go, which in hindsight made for a fairytale Yountville dinner upgrade story for me, more on that another time. Fortunately, Thomas Keller delivered. Course after course arrived like a masterclass, and somewhere along the way conversation gave way to eye contact and the occasional “this is ridiculous.” The kind of meal that quietly recalibrates your understanding of food, where you stop pretending you know what you’re tasting and simply accept that you’ve been doing it wrong for decades. Reservations harder to secure than Derby Mansion tickets or an Augusta membership, and worth every ounce of anticipation. Best meal of our lives. Unquestionably.
Apparently, I am destined to be the other Jeff. First to Bezos during my Amazon years, and now to Italian weddings. Because what followed was not a reception. It was an Umbrian takeover.
From September 1st through the 3rd, we gathered 77 of our closest friends and family, people we love and are doing life with, at Villa Valentini Bonaparte in Umbria. Seventy-seven. We were married on 7/7. Denise was born in 1977. My mom was 77. At some point you stop calling that coincidence and realize God might be making a point. Seven is completion. Seventy-seven is completion multiplied. When He speaks in patterns, you listen.
For three days, we stepped outside of time. Laughter echoed off ancient Italian stone walls, worship carried deep into the Umbrian nights, and every moment somehow felt both fleeting and eternal. We honored Denise’s father, Mr. Gitsham, whose presence was felt in every prayer and every embrace, a reminder that love does not leave when someone does. We honored my parents, who could not be there but were never absent in spirit. And then we danced under the stars. Volare to Purple Rain. Italy to Minnesota. Some moments you remember. Others you measure your life against. This was one of those.
And then came Reschio. Not just a hotel, but a place that feels like stepping backward in time while somehow living ahead of it. A thousand-year-old castle restored with obsessive precision. Rolling Umbrian hills. Silence that actually quiets you. Watching Denise on horseback, completely at ease, like time had folded in on itself and returned her to something familiar. Even the espresso arrives with purpose. It wasn’t just a honeymoon destination. It was the perfect place to begin our marriage.
Denise continues to step fully into her calling. Her voice is expanding beyond her NewsNation TV responsibilities into something deeper. She speaks truth. Not right versus left. Right versus wrong. Anchored in God and delivered with conviction that doesn’t require volume. She doesn’t chase platforms. Platforms find her. And when they do, truth follows.
Elle is on a tear. The kind where you stop giving advice and just try to keep up. College visits, essays, SATs, and lists that multiply faster than my betting tickets on Derby Day. She spent time in New York at Vogue’s Fashion Business program and is about to launch her own line like it’s a foregone conclusion. Somewhere between prom, passing her driver’s test, and confidently taking the keys, she has stepped fully into her independence. I am proud. I am impressed. And I am mostly trying to keep up while God keeps opening doors in front of her.
This year has carried both joy and weight. My mom has been battling Alzheimer’s and dementia for nearly nine years and recently suffered a heart attack. She is now in hospice care, and still making us laugh in ways only she can. Every smile feels like a gift. I owe so much to my sister and brother for their selfless commitment to caring for her and supporting my dad. They have been extraordinary.
My dad continues to inspire in his own way. Fully committed to my mom, he has taken control of his health, losing 30 pounds with a goal to lose ten more all to get back to the fairways. His discipline has been impressive. Denise deserves some credit there. She has a way of elevating those around her. Our prayers remain constant for both of my parents.
Our dog Jack, at 13, underwent brain surgery last June. By the grace of God and an incredible team at UC Davis, Jack is now 14 and you would never know it. A reminder that God is in the details, especially the ones we never would have chosen.
In December, we closed a chapter with our DC apartment and in July stepped into a new one with our new home, Grazia Tra Vigne "Grace among the vines." Located near Napa and minutes from where Denise grew up, this is not just a home. It is a gathering place. A place to build community. To create space where people encounter God and leave different than they arrived.
Before we moved in, the story had already begun. We circled the property in prayer, nearly every day, inspired by Mark Batterson’s Circle Maker, believing boldly for something that, at the time, did not feel guaranteed. And then God moved.
We wasted no time putting it to use. Denise’s mom’s 86th birthday brought together over 50 people, ages one to one hundred and one. Over New Year’s, we opened our doors again. Celebration first, then a prophetic class led by our dear friend Lindsey Reiman. Because if you are going to start a year, you might as well start it listening.
U.S. Congressman Doug LaMalfa and his wife Jill joined us on New Year's Day eating Denise's chili and having Jack become Doug's new best friend. Five short days later, Doug passed after receiving a heaven-sent prophetic word in our home. A sobering reminder of how quickly life moves. Weeks later, Denise delivered a deeply moving eulogy, grace-filled and anchored in truth. One of those moments you do not just hear. You carry with you.
What didn’t always make sense then is becoming clear to me now. Every step throughout my life has been preparation. Every role, every season, every unexpected turn. That preparation has led to something new professionally for me.
Not a company. A calling. A movement to restore honest money language to the Church and to Christian leaders who know something is broken but cannot yet fully articulate it. God has gifted me the ability to think in long arcs. Four hundred year cycles. Systems that shape nations, families, and stewardship itself. And I believe bitcoin represents a return to something foundational. Bitcoin is not a rebellion. It is a repentance as God cares about honest weights and measures.
Now, back to the puzzle. Life reminds us what matters. The Derby reminds us how little we control.
Twenty horses. A mile and a quarter. Two minutes that separate preparation from regret. This is where opinions get tested and conviction gets exposed.
Last year, the race unfolded exactly as I prophesized. Pace. Positioning. Patience. This year is less forgiving. A more open field, many moving parts, and just enough uncertainty to punish lazy assumptions.
This group doesn’t hand you an answer. It forces you to earn it. Morning Line favorite Renegade draws the rail, where trips are either surgical or suffocating. The Puma brings consistency without the need for attention. Chief Wallabee carries upside with unanswered questions. Emerging Market sits in that dangerous in-between, lightly raced and facing the curse of Leonatus (1883). Further Ado shows up off a number you can’t ignore. And sitting just off center stage is Commandment, not loud, not hidden, but checking boxes in all the right places.
No shortcuts here. Let’s break it down.
⚡ PACE SCENARIO
This Derby starts with pressure. Not reckless, but undeniable. From the outside, Six Speed has no choice it’s go or get hung wide into next week. That decision alone injects pace before they even hit the first turn. Inside, Litmus Test, Potente, and So Happy won’t concede position early. They do their best running forward, and they’ll commit to it.
The result is a lively opening. Expect a :22 and change first quarter, with the half landing around :46 flat. Quick enough to matter. Not fast enough to collapse.
That’s where the modern Derby reveals itself. Since the points system took hold in 2013, these races rarely melt down. Instead, they wear down. The leaders don’t stop. They soften just enough to invite the right horses into the race.
Which puts the focus squarely on the tactical runners. The Puma, Chief Wallabee, Emerging Market, Further Ado and Commandment all project to land in that ideal window, fourth through eighth early. Close enough to strike, far enough to avoid the early stress. Not chasing. Tracking. Waiting.
Behind them, the closers begin their calculus. Renegade, saving ground on the rail, will need timing and courage. Golden Tempo will be hoping for just a touch more heat, to bring their late runs into play.
The Derby isn’t won on the front anymore. And almost never from the clouds. It’s won in that narrow band where patience meets position. If this race unfolds the way it projects, the pace won’t give anything away. It will simply ask the right question at the right moment.
It won’t hand the race to anyone. It will expose who’s built for it.
HANDICAPPING THE DERBY
❌ SCRATCHED (3 Horses): (5) Right to Party (13) Silent Tactic, (20) Fulleffort
❌ TOSS (8 Horses): There are always horses you eliminate quickly. Not because they lack ability, but because this race demands something very specific—and not everyone is built for it.
(2) Albus, (3) Intrepido, (4 ) Litmus Test, (11) Incredibolt, (17) Six Speed, (21) Great White, (22) Ocelli, (23) Robusta
Some are too slow on figures. Others are too dependent on a pace scenario that doesn’t project. A few are simply being asked questions they haven’t shown they can answer. The Derby is not the place to hope for a breakthrough. It’s where exposed limitations get magnified.
(7) Danon Bourbon, (10) Wonder Dean, (16) Pavlovian
Danon Bourbon is undefeated, but untested at this level. Wonder Dean brings international intrigue and stamina, but class translation remains a question. Pavlovian now lands here—capable, but not convincing enough against this depth. These are the types that can hit underneath, inflate exotics, and make you wish you used them, just not on top.
🏆CONTENDERS (9 Horses)
(6) Commandment: Doesn’t force you to reach. Four wins from five starts, tactical speed, and proven at Churchill Downs. Into Mischief on top, Orb underneath ties him directly to the modern Derby blueprint. Doesn’t need chaos. Just needs the race to unfold the way it typically does.
(8) So Happy: Talent is real and the forward style fits, but he’ll be part of the early equation whether he wants to be or not. The question is whether he can carry that speed the full ten furlongs. Dangerous if he relaxes. Vulnerable if he doesn’t.
(9) The Puma: The most honest horse in the field. No flash, no noise, just consistent efforts against legitimate competition. Pedigree suggests the distance is well within range, and his versatility gives him options. In a race full of variables, he’s a steady constant.
(12) Chief Wallabee: This is where upside enters the picture. Lightly raced, improving, and adding blinkers with intent. Constitution pedigree leans stamina, and his running style fits the winning zone. Timing is everything. Move too early and he flattens. Move at the right moment and he’s a problem.
(14) Potente: Speed and raw ability put him here. Lightly raced, but talented enough to matter. Likely part of the early pace, which creates both opportunity and risk. If he clears and settles, he’s dangerous. If not, he’s part of the pressure that sets the race up for others.
(15) Emerging Market: The quiet climber. Undefeated, lightly raced, and still improving. Up against the curse of Leonatus. 1883 was last time a horse with only 2 career starts won Derby. Pedigree supports the distance, and his style keeps him clear of early trouble. Doesn’t need to be best early, just needs to stay relevant long enough for his upside to matter late.
(18) Further Ado: Brings the flash. Fastest last-out figure in the field. The kind that forces a decision: believe it or fade it. Talent is real, but from a wide draw in a chaotic race, he has to prove that number travels.
(19) Golden Tempo: The deeper runner with stamina and the right profile if things soften late. Not the most likely winner, but exactly the type who picks up the pieces when others begin to weaken.
RIDERS UP!
2026 DERBY SELECTION
COMMANDMENT (6)
Last year it was Sovereignty. The race unfolded exactly as it had been suggesting all week with pace, positioning, patience. It felt less like handicapping and more like alignment. Scripture says, “The horse is made ready for the day of battle, but victory belongs to the Lord." Twenty showed up prepared. One left crowned. And somehow, it felt inevitable.
This year, the noise is back. New names, new narratives, new ways to overthink what is often far simpler than we allow. But beneath it all, the same truth holds. This race rewards order, not chaos. Discipline, not desperation.
In a field with Renegades and rising markets, the answer isn’t rebellion or noise. It’s order. It’s alignment. It’s (6) Commandment. Not just a name. A signal. In Scripture, commandments are not suggestions. They are order. They are alignment. And in a race defined by pressure and timing, that matters. He checks every box. Tactical speed. Proven pattern. A pedigree that fits the modern Derby blueprint, Into Mischief over Orb, Riders Up 2013 selection that won this race, tying him back to the foundation of this era. Trained by Brad Cox, surrounded by intention, not noise.
He doesn’t need chaos. He needs the race to unfold. And when things unfold the way they are supposed to, you don’t force it. You recognize it. That’s the edge.
Because the Derby isn’t won by the loudest horse. It’s won by the one still standing when the questions get hard in the final furlong. When pace softens. When positioning matters. When everything else fades.
Last year, Sovereignty set the tone. This year, Commandment answers the call.
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| Commandment and his mom Sippican Harbor |
Riders Up! See You in the Winner's Circle.
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