Kentucky Derby, Minnesota Style
Todd Swank's Diary Entry for May 4, 2025
On Saturday, Miss Sheri and I made our annual pilgrimage to the classiest place in Shakopee with a betting window — Canterbury Downs — to celebrate the Kentucky Derby the only way we know how: surrounded by strangers in wild hats, pretending we understand horse racing, and hoping the drinks hit before the losses do.
We’ve been coming to Canterbury Downs for decades, and it never disappoints. The place knows how to throw a party — especially on Derby Day. While they don’t kick off their live racing season until May 24, the Kentucky Derby celebration still brings in a packed crowd, themed activities, and enough excitement to make you wish the horses were running a little early.
It feels like the crowd for this event gets bigger every year — which makes it a blast when everyone’s cheering at the same time for a horse race happening on a giant screen in the middle of the field. The only downside? The bar lines are starting to feel like their own endurance event. I came here to place bets, not survive a hydration crisis.
We were lucky to run into these two stylish ladies — Heidi Wojahn and Diane Ball — who brought great energy and even better Derby fashion. Always a treat to see familiar smiles in a crowd this big.
One of my favorite parts of Derby Day is seeing how far people take the fashion. The hats were absolutely unhinged in the best way — towering feathers, flowers, miniature horses… you name it. They even held a “Best Hat” contest, and while the finalists brought the heat, a little girl ended up winning the top prize. Cute? Sure. Deserved? Debatable. Personally, we thought the woman on the right should’ve walked away with the crown — or at least a neck brace.
Between races, the crowd got treated to a performance by Pop Rocks — a high-energy band that reminded me a lot of Hairball, just with more costume changes and slightly less pyro. I especially enjoyed the guy channeling Ozzy Osbourne; he had the look, the snarl, and even the bat-free stage presence. Founded in 2006, Pop Rocks rotates singers impersonating music legends from Katy Perry to Garth Brooks, with over 30 wild costume changes in a single show. Honestly, it felt like karaoke night at Comic-Con — and I mean that in the best way possible.
Then this happened — and my inner 20-something just about lost it. When the Pop Rocks performer stepped out in full Britney Spears mode, red bodysuit and all, it was like being dropped straight into a late-'90s music video flashback. I’ve always been a big Britney fan, so this one hit me right in the nostalgia. And yeah... I may or may not have mouthed the words “hit me baby one more time.”
For the first time, we got a good look at the new amphitheater rising behind Canterbury — and it’s already looking impressive. Set to open in summer 2025, the venue will seat up to 19,000 and host 30 to 45 concerts a year, operated by Live Nation. With Canterbury Park, Valleyfair, Mystic Lake, and the Renaissance Festival all in shouting distance, Shakopee’s about to go from “pretty fun” to “pack your weekend bag.”
Before long, it was time for the big event — the 151st running of the Kentucky Derby. We all gathered around the giant screen like it was the Super Bowl of horses, and it didn’t disappoint. Journalism looked like it had it in the bag, but Sovereignty came storming down the stretch and stole the glory. A muddy track, a dramatic finish, and a jockey who'd recently been hospitalized… you couldn’t script it better unless you were trying to win an Emmy. Horse racing might be chaos, but it's thrilling chaos.
Like I do far too often these days, I asked ChatGPT how to bet $20 on the Derby in a way that balanced safe picks with a few wild long shots. I’d love to say my strategy crushed it… but the real winner was Miss Sheri. She copied the structure but picked her own horses — including Sovereignty and Journalism — and hit an exacta box and an across-the-board bet. She walked away $94 richer, and since we only wagered around $50 total, that made us official Canterbury winners. Thank you, artificial intelligence. You may not have picked the horses, but you definitely helped pick the winner.
We keep spotting this adult and juvenile bald eagle pair along the creek near our house. They’ve been hunting in the area for weeks, and I can’t stop stalking them like some kind of feathered paparazzi. I know eagles are a lot more common these days, but when I was a kid, they were practically mythical — endangered and almost never seen in the wild. So yeah… every time I see one, it still stops me in my tracks.
This was the closest I’ve gotten to one in a while — close enough to feel like he was silently judging me for not having wings or a better zoom lens. I’d say it was majestic, but honestly, he looked like he was moments away from filing a restraining order.
And just like that, the sun sets on another chaotic, colorful, and oddly bird-obsessed week in our lives. Whether it’s betting long shots, stalking eagles, or reliving our Britney years at the racetrack, we somehow keep finding ways to make the most out of Minnesota spring. See you next week—same time, less sanity.
@toddswank In honor of Rudy Gobert’s huge game against the Lakers last night… I used Kling AI to bring this photo to life. We met by the elevator last summer. Now we’re both celebrating the Wolves taking Round 1! #KlingAI #Timberwolves #RudyGobert #NBAPlayoffs #AIvideo #WolvesWin #lakers #AIMagic ♬ original sound - WorthTheReplay
@toddswank I love slot machines!! #gambling #casino #slots ♬ Let's Go - JAXSON GAMBLE
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