My father never really retired. He worked for himself as a real estate broker/investor in the Washington, D.C. area for my entire life. So even when he was well into his 80s, he was out and about. My dad liked numbers, ones that spoke to him, that felt like an advantage even if the advantage was slight. So, it was no secret he’d be drawn to horse racing in the same way he’d be drawn to a property that — with the right touch — could yield a return.

He taught me how to read a Daily Racing Form before he taught me how to throw a ball. He’d take me to Rosecroft Raceway in suburban Washington to watch the trotters run at night. At 8, being anywhere in the evening was beyond exciting, and when the show bets he funded hit, we celebrated shared time and being right.

Fans enjoy the action at Saratoga Race Course. (Penelope P. Miller/America's Best Racing)

Horse racing was one of our consistent links in life. As I grew older, I wanted to make sure that we remained close and I used the sport to ensure it. We partnered on a low-level entry into a syndicate that ran racehorses at Laurel Park. We went to the Belmont Stakes together in 2008 when Big Brown was supposed to end the long Triple Crown drought and, although we didn’t see history, a hunch play on the massive dog Da’ Tara paid for the trip. And when I moved to Connecticut to work for ESPN, we made the pilgrimage to Saratoga Race Course in Saratoga Springs, N.Y., to take a step back in time together.

I lost my dad seven years ago. He slipped and broke his hip and his age and health didn’t allow him to heal. There is a picture of my father holding my infant son, one of the few that exists. It’s too bad because my son reminds me of my father every day. Both were social creatures. Both gregarious and funny. And I know that the three of us could have ended up at the Preakness or a winner’s circle or just watching the Derby together one day.

I thought a lot about my father this past weekend in Saratoga Springs, where I turned the end of a family road trip through New York’s mountains and lakes into a formal introduction into a sport I hope connects my kids (son and daughter) to me the way it connected me to my father.

Fans experience horses at Saratoga. (Penelope P. Miller/America's Best Racing)

This task won’t be easy. Things are different now. My son and daughter have access to everything the modern world offers. I wasn’t sheltered, but YouTube, Fortnite, and Twitter didn’t exist. And so, my world could be curated through the lens of an attentive parent who, in hindsight, clearly wanted me to be close to him forever. And I want that, too. I want my kids to follow their passions and interests — I certainly did all the way to dream jobs at ESPN and calling the Washington Football Team games — even if they aren’t the ones I chased. But I also want them to take on the responsibility of being part of my life as much as I will be part of their lives. So, I made sure they got out their best pink dress shirt and colorful sundress, a dapper hat, and some cool shades to join me at the Spa for an induction into a connection we can have, if they so choose.

Horse racing was a chance for my father to chase excitement with his son and offer some wisdom about analytical thinking. You can’t always be right, but you can make some judgments and, if your judgment is sound, you’ll have no regrets at the results. He often stared down the tote board until the last minute, waiting for shifts in the odds, and expressed the idea that thinking you know everything is the folly of egotistical losers. Sometimes you need to follow the information even if it is counter to your initial conclusions. More importantly, we just talked. Many of my most intimate conversations with my dad took place while scouring the racing form for a pick in the next race. He learned about my girlfriends, my work, and my life. I picked his brain when I needed some advice, and often we’d end up on a ticket that had way too many horses to ensure a decent profit, if any, but I think he knew just seeing our numbers come in would be worth the modest loss. A shared experience of winning is more valuable than a solitary hit on a longshot.

This wasn’t the first time my kids went to a track with me. My son accompanied me to Maryland Million Day at Laurel Park, and my daughter was born on the day of the Kentucky Derby in 2009, so reminding her of that link is a tradition. But this was the first time I asked them to see a lifestyle choice I’ve made and subconsciously asked them to indulge my interests. Saratoga felt like the perfect spot to send that message.

Fans cheer home a winner at Saratoga. (Penelope P. Miller/America's Best Racing)

We walked the main streets of Saratoga Springs that morning. Stores feel like they are mandated to have horse racing goods of all sorts: pillows, games, magnets, glassware, sweaters, purses, you name it. There is an old-time charm that is emphasized when you cross into the race course itself with its carnival-like setup, where the horses walk through the crowd on their way to the track. The colors have a carousel-like feel. There is live music playing and food for all tastes of the palate. The grandstand itself is a step back in time; it screams tradition and regal beauty. And it didn’t hurt that I have the connections to have box seats on the finish line (thanks, ABR). It also didn’t hurt when my son asked me to pick a winner and two out of the three races we wagered on together, we won (thanks, karma).

We were dressed to the nines as a family. We shared the beauty, the laughs, and thankfully, a couple of wins. And this is the message I wanted to send. I love travel, sports, well-appointed atmospheres, and the opportunity to be part of something special. Want to go to Del Mar or Santa Anita Park or Belmont Park or Ascot or Hong Kong? This dad, like my dad would be down for that kind of experience.

Horse racing gave me and my father a connection. It may or may not do the same for my kids, but I view it as a perfect vehicle to try: travel, fashion, lifestyle, and a chance to celebrate together as bettors, owners, or just people spending time together. In the end, it won’t matter if our horse comes in first, I’ll have already won.