Derek Isenberg’s Road to Victory in the Players Championship Wasn’t Very Convenient, but it Sure Was Rewarding

If the story of Derek Isenberg’s $125,423 triumph in the $334,464 Players Championship were made into a movie, it would probably be a cross between Let it Ride and National Lampoon’s Vacation. That’s because while Isenberg and 191 others were entering their selections for Day 1 of the two-day competition, he and his wife Raluca were simultaneously loading themselves and their three children—ages 14, 13 and 6—into the family car (truckster?) for a long driving trip from their suburban Philadelphia home in Haddon Heights, N.J. to Tennessee, where the final stop would be Memphis.

The trip still continues. The Isenbergs won’t be back home until Sunday. However, much of the plot has already played out. And unless Derek later reports that Graceland was closed for repairs when he got there, the Isenbergs’ trip—unlike the Griswolds’—can be deemed nothing short of a smash success.

Derek, 49, has the klnd of job that probably makes extended, “get-away-from-it-all” vacations a must. He spends about half his time working as an emergency physician at Temple Hospital in North Philadelphia.

“You can imagine some of the stuff I see,” he said.

The other half of his professional time is more serene. He teaches residents at Temple University’s Lewis Katz School of Medicine.

Somehow—between painstaking lesson planning, lengthy classroom lectures and highly intense days in and around the ER—Derek finds time to play nearly every day at HorseTourneys…even on Mondays and Tuesdays.

“Those are my Parx days!” he laughed.

A week or two prior to the Players Championship, Derek won a $2,000 entry for it in a qualifier. He knew that the event conflicted with his long-planned trip, but he didn’t think it would interfere too much. He could just play it as though it were a Pick & Pray—and that’s what he did on Friday. He figured he could see how he was doing on Friday night and then come up with some Day 2 picks on Saturday morning that were appropriate to his position on the leaderboard.

At the end of Friday’s action, Derek was in 11th place—$67.82 behind the leader, Jim Cuzzupe.

“I thought I was in good position to make a run,” Derek recalled. “I was cautiously optimistic. I had had a decent first day. I knew I didn’t have to pick all long prices like I would have had I been behind by more.”

So he put in his Saturday picks, and then, of course, it was time to do more driving.

Similar to Friday, Derek wasn’t watching live during the first half of Saturday. He’d check the leaderboard every hour or so—and, early on Saturday, he probably didn’t like what he was seeing. From his first six plays, he had connected on just a couple of modest place collections. 

Isenberg tried to look at the bright side.

“I don’t remember anyone pulling away at that point, and there were no long prices in the first half of the second day,” he said. “I was sticking with my original plays, and I had a couple of longer prices coming up soon. I figured, ‘If one of these hits, great. If not, I’m probably done. I won’t be able to make up the money.”

The first of those longshots—Fionello—was coming in the 4th at Santa Anita at 4:40 pm ET. The other one was right on its heels—Storm’s Wake in the 8th at Keeneland. Post time: 4:45 pm ET.

Wouldn’t you know? Right around 4:30 p.m., the kids in the back of the car started getting hungry and wanted to pull over at a rest area near Pigeon Forge, Tennessee, for a bite to eat. (At least that’s how Derek remembers it.)

As the kids reached for their sandwiches, Derek reached for his phone. It was almost post time for the 4th at The Great Race Place.

Six-horse fields like that in the 4th at Santa Anita are not always fertile ground for contest-changing plays, but Isenberg tries not to dismiss them too quickly. 

“Especially when there’s a strong favorite,” he explained. “Sometimes people just dismiss the others. I’m a pace handicapper. I thought the Santa Anita race had a lot of pressure in it, and that the two favorites were both pretty ‘early’ horses. I thought the 2 horse was the good closer. Luckily that’s what happened.

The 18-1 odds on Fionello gave Derek reason to think he might now be in serious contention—especially given the paucity of big prices to that point in the day. Before he could give that much thought, though, it was time to switch over to Keeneland.

“Storm’s Wake…I knew she had a really strong late kick. I really didn’t like the favorite in the race, Sister Troienne. At Gulfstream, she was running very forward. I didn’t think that style would play as well at Keeneland.”

Somebody hand that man a sandwich. For the second time in five minutes, Derek had nailed a longshot winner.

“Wow, I just took a big lead,” he said to himself. “I have a chance to win.”

In case you think the Isenbergs left the rest area and were hooting and hollering all the way to their next stop, that’s not how the family dynamic works.

“My wife Raluca was happy for me, but she’s a little fatalistic when it comes to these contests,” Derek related. “She knew there were still a lot of races left.”

Indeed, she did. “Just tell me when it’s all done,” she told Derek.

Isenberg now had the lead, and he had seven picks left…

…but the next six didn’t go his way. He had but one $5.24 place payoff to show for them. Was he starting to second-guess himself? Was doubt creeping in?

“I did not change my strategy,” he said. “I stuck with the picks I had made earlier in the day. As I missed, though, I did start to wish that I had some of my picks back so that I could play more late in the day. There was one horse I played that I thought would be 7-1 that went off at 5-2, and I couldn’t really make changes being on the road like we were.”

By the time of the next-to-last contest race, Isenberg had just one play remaining, and he had fallen back to third place, $27.96 behind leader Hayden Leibrock. What was a dad on a driving vacation with his family to do?

What else? Stop at another rest area!

This time, the stop was made at a Buc-ees elsewhere in Tennessee.

“It’s like a Wa-Wa on steroids,” Derek explained to someone who had never been in a Buc-ees. “It’s a convenience store, but it’s huge with all kinds of fresh meat and brisket sandwiches and snacks. They even have a clothing section.”

Buc-ees was easily the kind of place where Raluca and the kids could occupy themselves for 30 or 40 minutes. Meanwhile, the next race at Santa Anita was about 10 minutes away with the final race of the contest coming a half-hour after that. How convenient!

While four of the Isenbergs went inside to peruse the many varieties of slushies and caramel puffs, Derek stayed in the car, trying to decide how to approach the final two races of the Players Championship.

“I knew I wasn’t going to play the last race,” he said firmly. “Breeding and trainer/jockey combinations aren’t really a strength for me, and there were three first-time starters in the last one. So that brought me to the 11th race at Santa Anita. I thought the favorite looked strong, and I was only 20 cents out of second place, so I briefly considered playing the favorite to try and get second place.”

Derek’s eye, however, kept going back to longshot Spirited Boss, a Florida shipper, who would be turning back in distance from a mile and a sixteenth on grass to 6 1/2 furlongs down the hill on grass. Ironically, this—like the Fionello race—was a field of six.

“She had some nice late fractions from Gulfstream,” Derek remembered about Spirited Boss. “I decided to go for it.

What the leaderboard like like while Santa Anita race 11 was taking place

“I wasn’t sure she’d be close enough to kick, but she sure did.”

And how.

Suddenly in front by nearly $30 with no more plays left—and with his family still inside Buc-ees—Derek had one more race to sweat out, the 12th at Santa Anita, a maiden turf race with a field of 11.

“It was nerve-racking, but it was exciting, though,” said Derek. “It was nerve-racking because a lot of odds drifted up. At first, only half of the field could beat me. Eventually, seven of them went off at double-digit odds. When the race went off, I quickly did a refresh to see who had who. It looked like only two or three of them could beat me. When I saw that I started feeling good.”

When the two that, indeed, could beat him started fading back in the pack, Derek felt even better. Those two wound up last and next-to-last—pretty much the perfect “root against” race. 

A few minutes later, he had some pleasant news to tell his patient wife and their three well-fed children.

“Raluca was delighted, but we haven’t discussed yet what we’ll do with the money…other than to maybe stay in some nicer hotels and have a few nicer meals during the rest of this trip,” Derek chuckled. “We’re both very practical. I know that we’ll save some for the kids’ college…and that I’ll use some to fund future HorseTourneys entries!”

In the coming days, Derek will have some very pleasant memories to help him pass the time during the long drive back from Tennessee to South Jersey. Many of those memories involve family and friends.

His love of horse racing (and probably road trips) were sparked by going with his father to the Meadowlands for harness racing when Derek was a teen, growing up in North Jersey. Later, they took many longer journeys together visiting racetracks and minor league ballparks…typically squeezing one of each in per day.

He also feels he owes a debt of gratitude to his his “Table 24” table-mates from one of his early appearances at the NHC. It’s a group that includes 2015 NHC champion John O’Neil and 2021 Flo-Cal Faceoff victor Alan Levitt. 

“We all became great friends, and they were texting me during and after the Players Championship, offering their support.”

With three young children at home and a demanding career occupying most of his time, suddenly bouncing around from contest to contest at tracks around the country isn’t really practical for Derek. His go-to contests have been—and will continue to be—the NHC, in which he has played 12 times, and the Monmouth Pick Your Prize tournament. 

Before either of those, though, comes the next leg of the 2026 HT Champions Series, the $200,000 Gtd. New York, New York Challenge. Perhaps Derek Isenberg will be playing it from a convenience store near you.

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