The 151st Kentucky Derby is upon us, and with it, the 27th installment of Riders Up!, a tradition that began 30 years ago with a youthful hunch on Thunder Gulch (1995) and a collegial weekend with my closest Notre Dame friends. That day we went from the infield (outhouse) to the paddock (penthouse), grunge-clad in Doc Martens, shorts, and flannels, somehow mistaken for Pearl Jam while rubbing shoulders with Bo Derek. That fever dream sparked a yearly ritual now steeped in film study, form cycles, and writing about the past year in my life. Thankfully, my wardrobe has upgraded, hat tip to Brunello Cucinelli. It’s been over two decades since I stood beneath the Twin Spires on Derby weekend, a streak that must end soon with a dear friends, DRF in one hand, and a view from the Woodford Reserve Paddock Club. So cue “My Old Kentucky Home,” raise a glass, and let’s chase greatness once more.
Last June, James, Elle, and I went full Eat, Pray, Parent across Italy, soaking up ancient history in Rome and spending a humbling day at the Vatican, where we narrowly missed seeing Pope Francis (God bless him). Here's to the conclave ushering in white smoke and a worthy shepherd. From there, we zipped along the Amalfi Coast like Bond villains on a private boat, and galivanting through Florence on a perfectly unstructured day built around gelato, laughs, and just enough shopping to test the luggage zippers. Elle critiqued street fashion with Vogue-worthy precision, while James delivered dry one-liners sharper than a Roman gladiator’s sword. Between dodging Vespas and debating whether Michelangelo or cacio e pepe is Italy’s greatest gift to the world, we made memories as timeless as the cobblestones beneath our feet.
James is 18, four weeks from donning cap and gown, and ready to trade high school halls for hacking firewalls at Full Sail University, where he’ll study Information Technology and Cybersecurity. Still chanting COYS with conviction (despite Spurs’ lifelong vow to test his faith), I’m hoping he takes Tottenham's motto “To Dare is to Do” seriously, especially the do part. His dry wit keeps us all in stitches, and in June we chased his football passion to Germany for Euro 2024, catching England vs. Denmark and Netherlands vs. France. If cyber threats fear him even half as much as he fears missing a Legendary Pokémon, I’d say the internet is in very safe hands.
Elle, 15 going on CEO, is a high school sophomore already deep in the college tour circuit withThanksgiving weekend saw us roaming UCLA, USC, and Pepperdine campuses, though the final runway is still TBD. Her discipline and drive paid off with a golden ticket to New York this summer for Vogue’s Fashion Business School, where she’ll study the creative and commercial forces behind haute couture. In July, we took a father-daughter getaway to London, only confirmed what I already knew: her eye for style is razor sharp. She’s clearly destined to elevate the family’s fashion standards to entirely new runway-ready and business-savvy heights.
Since leaving
AWS and then
Blockdaemon in 2023, I’ve been semi-retired, thank you bitcoin, and exploring that elusive sweet spot between sabbatical and strategic drift. I traded boardrooms for bodywork, swapped KPIs for Korean skincare, and dove headfirst into self-care including recently returning from a rejuvenation in Seoul that had me feeling like Benjamin Button. I also spent a transformative week at the Hoffman Institute, which essentially upgraded my spiritual WiFi from dial-up to fiber. Amid all that inner rewiring, I’ve kept my heart close to home, continually praying for my parents’ health, who gave me every opportunity to succeed. Love you,
Mom and
Dad.
These days, my compass points firmly toward obedience tuning into what God has planned for me both personally and professionally. I’m entertaining new opportunities, but I’ve come to learn that growth doesn’t always arrive in pitch decks or job offers; sometimes it whispers through stillness, surrender, and sacred timing. And that quiet obedience? It led me to the once-in-many-lifetimes woman.
Exactly one year ago today, I was putting the finishing touches on my 26th Riders Up! likely sleep deprived and over-confident in my selection unaware that the real headline that day wouldn’t be about horses, but a first date. That night, I met Denise, and May 2nd, 2024, changed my life forever. Due to us both traveling it took 96 days from swiping right on Bumble (January 28) to finally meet in Yountville (longer than most congressional bills take to die in committee), but worth every moment. I’ll let her tell the full story, it’s better with her delivery. I’ll never forget her outfit, shoes, the sparkle in her eyes, the hours of conversation, and the fact that we said grace before the meal. God was there at the start, and He’s been at the center ever since.
Denise is the most beautiful woman I’ve ever met, inside and out. She has the largest heart of any human, authentic, brilliant, rooted in truth, God-loving, and the only person I know who can light up a NewsNation segment and write a book that both sides of the aisle should read Politics for People Who Hate Politics . Since that first date, we’ve been inseparable. Our second date? Vegas. Delilah. She wasn’t convinced I could actually get her and her friends a table to celebrate her birthday as they tried unsuccessfully. Thankfully she invited me to meet her and possibly call my bluff while I confidently delivered a Royal Flush.
Since then, we’ve hopscotched the globe, racking up memories from Minnesota to D.C. onto Nashville, Austin to Montana, with stops in Aspen, San Diego, Dallas, Houston, Chicago, West Palm, Miami, Charleston, and Norfolk—plus international chapters in London, Taipei, and Seoul. And then there was our dreamy escape to the Grand-Hôtel du Cap-Ferrat, followed by what I humbly declare the finest hotel on Earth:
Passalacqua on Lake Como, where even the Negronis felt like a love letter.
My love for her has only grown stronger with every prayer, every mile, every laugh. God works mysteriously on His time and we came into one another's lives at the right moment. An example of how we get one another, around 2am on Election Night, sitting in the NewsNation green room, after buying George Will a cheeseburger and chatted all things Minnesota with Governor Pawlenty, we decided then and there to submit an application on an apartment in our nation's capital. Her TV career and PR firm is blooming like the April cherry blossoms, and with a crypto-friendly administration (finally), it makes perfect sense - oh BTW yes Denise and I "drop(ped) it like it's hot" hanging with Snoop at The Crypto Ball during the inauguration.
A few weeks later, on our 9th monthaversary, I proposed at the Caribou Club in Aspen and she said yes. As if God wanted to leave no doubt He was in on it, there was a Bumble pop-up shop
next door. Divine sense of humor: confirmed. Today marks one year since I first laid eyes on the woman who made me believe in forever, and I can’t wait to hold her hand for, God willing, the next six decades (and beyond). Once this Derby selection is locked in, it’s back to wedding planning as we prepare to celebrate with our closest friends and family this September in Umbria, Italy. And while I’ve had my share of winning picks over the years...
Denise will forever be my greatest selection.
The 151st Kentucky Derby isn’t just fast horses and mint juleps, it’s layered drama at full gallop. Bob Baffert returns from exile with Citizen Bull, the former 2-year-old champ now stuck on the rail and chasing redemption from the dreaded one-hole.
Atop the talent board is favorite Journalism, the unbeaten Curlin colt with push-button gears and big-horse energy. If the speed melts down, he may turn this into a headline rout. Sovereignty brings late firepower, Godolphin polish, and a name fit for a sermon, divine order in a chaotic stampede. And don’t sleep on Sandman, the surging gray who could cue Metallica as he "enters" the stretch. Ten years after American Pharoah’s historic run, Derby 151 feels primed for another unforgettable chapter.
Pace Scenario
The 2025 Kentucky Derby is shaping up to be a fast-paced contest, with several frontrunners poised to set a brisk early tempo. Notable speed horses include Citizen Bull, Neoequos, East Avenue, and Owen Almighty. All of whom like to be forwardly placed. Based on past races and current form, the opening quarter could approach 22.5 seconds, with the half-mile potentially just under 46 seconds. This is fast, but not quite historically blazing. For context, some of the swiftest early Derby paces came in 2001 (22.25 / 44.86), 1981 (22.2 / 45.2), and 2013 (22.57 / 45.33), the latter of which was notably the first year under the current points-based qualification system that de-emphasizes sprint races and tends to filter out pure speed horses.
Since the advent of the Derby points system in 2013, Derby paces have generally moderated compared to the wild early splits seen in the 1990s and early 2000s, when horses like Songandaprayer or Spanish Chestnut scorched the opening half before folding. Still, a sub 46 half-mile would be among the fastest of the points-era, and could test the resolve of early leaders.
Such fractions would favor stalkers and closers. Horses like Journalism with tactical speed and a push-button kick are well positioned to pounce. Sandman and Sovereignty, both proven stretch runners with stamina-friendly pedigrees, loom large if the pace melts down late. It's all about navigating traffic!
Handicapping the Derby
Derby Winner Profile: Post 2013 Point System Era (2013-2024)
Riders Up! has been flailing at the finish line since the Derby Point System trotted onto the scene in 2013. In 12 years, I’ve managed just 1 Win (Orb), 1 Place (Tiz the Law), and a modest 4 Shows. So this year it's all about the data.
Since 2013, a clear Derby Winner Profile has emerged:
-
Running Style: Tactical stalkers and mid-pack closers dominate. Authentic (2020) is the lone wire-to-wire winner in anomaly COVID year when Derby was in September.
-
Final Prep: Every winner finished 1st or 2nd in their final prep.
-
Final Fractions: The “Final Fractions Double Qualifier” (FFDQ) theory lives on with last 3/8 < 38.00 sec and last 1/8 < 13.00 sec signals stamina and finishing power.
-
Speed Figures: Winners regularly post a Beyer >95 and TimeformUS late pace >100.
-
Pedigree: Names like Curlin, Tapit, Into Mischief, and Empire Maker show up again and again. Dosage Index under 4.00 is the sweet spot.
-
Strikes System: Most winners have 0–2 “strikes” using Jon White’s historical benchmarks.
2025 Derby Selection Sponsor
Riders Up! 2025 Derby Selection
18 Sovereignty
Sovereignty – Kingdom-Bred,
Bitcoin-Backed, and Born for Glory
Born on 2/22/22. Yes meaning twos are wild
and providence whispers louder than odds. Sovereignty is more than a name, it’s
a statement, In the Bible, sovereignty reflects God’s ultimate rule. Fitting
for a colt owned by Godolphin, a place I visited last year while in Dubai. Now,
he charges into the first Saturday in May as a third-time starter off a layoff,
primed to peak, flashing a 114 Timeform late pace figure, Final Fractions
Double Qualifier credentials, and a classic closing style built for 10
furlongs.
His pedigree is inbred to my
second favorite horse ever, Seattle Slew, who won the Triple Crown in 1977 which happened to be the year Denise was born while also having ties to my favorite
horse of all-time, Secretariat, who won the Triple Crown the year I was born. And somehow
it all feels intentional like bitcoin, powerful, inevitable, and decentralized
from all chaos. When the gates open, I’m not just betting a horse, I’m backing
a higher plan!!
I flirted with the favorite, Journalism, as he’s clearly the class of the field. It felt a little too familiar, like last year’s ill-fated romance with Fierceness. Sandman had his appeal too (cue Metallica), especially on the 20th anniversary of last gray to win, Giacomo’s shocking glory in 2005. But in the end, I’m sticking with my first instinct and you know what they say, trust your gut, especially when it's Kingdom-aligned.
*** SATURDAY UPDATE DUE TO SLOPPY CONDITIONS.
I will continue with my selections, however from a betting perspective there are things to consider. note that I look at Tomlinson ratings and feel this could benefit a few horses while impacting others. I have added a column to my analysis above.
Tomlinson Ratings are pedigree-based scores (0-480) predicting a horse's ability on a specific surface, with higher numbers favoring stronger genetic suitability, especially on wet tracks.
Still like my top 3 Sovereignty, Journalism, Sandman with rain. Track conditions improve chances for Citizen Bull, Final Gambit, Burnham Square, East Avenue while bringing in longer shots that could hit the board Owen Almighty, American Purpose. It could negatively impact Luxor Cafe, Tiztastic, Baeza
Riders Up! See You in the Winner's Circle.
