Derby Day at the Plaza

The attendees of the Derby Day hat contest at the Plaza Hotel’s Rose Club on Saturday, like our farflung friends, the voting public of Greece and France, seemed to be chafing under self-imposed austerity measures.

In the lead-up to post time, Neil Rosen, on-air movie critic for NY1, sauntered up to us and wantonly flirted, “Are you looking for me?” We weren’t, but a miffed bartender with a thin ponytail was. “Where is your friend who bought that glass of red? He didn’t pay.” Mr. Rosen sheepishly admitted he didn’t know where his friend was, and he balked after the bartender trotted off. “That’s guilt by association! I shouldn’t have to pay.”

Elise Kamp, visiting from Connecticut, marveled at the cost of her glass of wine as she took in the pre-race coverage on the bar’s TV screen. “You could probably go to the Kentucky Derby for what it costs for dinner here. But the horses are beautiful. You can get big money from their sperm,” she noted matter-of-factly. (Her pick to win? “Gemologist—I love jewelry.”)

A piddly pot of dollar bets cropped up next to us at the bar, and an informal survey of other pursestring-pulling patrons concluded that that was the most anyone cared to wager.

And then, the race. Two minutes of hooting and hollering later, we had a winner. But despite the victorious horse’s name—I’ll Have Another—a neighbor warned us, “Don’t order a second mint julep. They’re $22.”

Two blonde friends, Ashley Parker and Ashley Colson, both in black-and-white dresses with red accessories, perched at the bar with a seersucker-suited friend, were the clear winners of the hat contest, and were handed a massive bottle of special edition Derby Day Woodford Reserve bourbon. But how to share the prize?

The Ashleys viewed the bottle as windfall that they could turn into an investment. “We shouldn’t drink it. It’ll be worth so much in a five years, we can sell it,” Ms. Parker said. “And if she drinks it before then, she owes me whatever it’s worth!” added Ms. Coulson. They shook hands to cement the agreement.

In the men’s division of the hat contest, octogenarian Philip Beekman won for his simple straw fedora. Would he make good use of the bourbon? “Oh, absolutely. God gave me a gift: I never get hangovers,” he said.

Does he watch the Derby at the Plaza every year? “No. I live in Florida and can only be in New York City 183 days a year.” Ah, to avoid those hefty New York City resident taxes!

“That’s right. I might have to move to Montclair if they don’t lay off me,” he said.