Trip Whitmore on Island Life: "We're Basically Locals"

I met Prescott "Trip" Whitmore IV at Cru, where he arrived twenty minutes late wearing Nantucket Reds, boat shoes, and a fleece vest despite it being 84 degrees. He'd parked his white Range Rover in a handicap spot "just for a sec." It remained there for ninety minutes.

Dee: How long has your family been coming to Nantucket?

Trip: Forever. Generations.

Dee: How many generations?

Trip: Well, my dad started coming in 2009, and now I come, so—two. Two generations. Which is basically—

Dee: Sixteen years.

Trip: In island time? That's like a century.

Dee: It isn't.

Trip: It's about commitment, not calendars. We're not tourists. We have a house.

Dee: That you're in for six weeks a year.

Trip: Eight, actually. Nine if you count Stroll.

Dee: You've written about the crisis at the FBO—

Trip: Finally, someone gets it.

Dee: —where your father waited 47 minutes at the private jet terminal.

Trip: Forty-seven minutes, Dee. At the private terminal. The whole point of a private terminal is that it's not the regular terminal. If I wanted to wait, I'd fly commercial. [shudders]

Dee: I took the ferry here. It was two and a half hours.

Trip: [stares blankly] I don't understand the connection.

Dee: You mention a "Richard" in your columns. A CEO you're friends with?

Trip: Great guy. Owns his own jet. Not fractional—owns it.

Dee: What's Richard's last name?

Trip: I don't really do last names. It's a WASP thing.

Dee: How many times have you spoken to Richard?

Trip: Define "spoken."

Dee: Words, out loud, to each other.

Trip: Once. But he nodded at me a second time, at the Field & Oar Club. You can't fake a nod like that.

Dee: What do you do for work?

Trip: Venture capital.

Dee: What does that involve, day to day?

Trip: [long pause] I take calls. From the porch. And I forward emails to people who—you know, it's very complex, I don't want to bore you.

Dee: Try me.

Trip: [longer pause] I add value.

Dee: Dotty Coffin's family has been here since 1821. She called summer families like yours "sixteen-year locusts."

Trip: Dotty and I are actually very close.

Dee: She said she doesn't know who you are.

Trip: Well, she knows my vibe. We had a moment at the Downflake once. Eye contact. Very meaningful.

Dee: She was probably glaring.

Trip: Agree to disagree.

Dee: You've written that "the island is being loved to death by people who don't understand it." Who are those people?

Trip: Day-trippers. Ferry people. The ones who show up with coolers. [whispers] Styrofoam coolers.

Dee: And your family, flying in on a Gulfstream—

Trip: G550, actually. The G650 waitlist was absurd.

Dee: —that's different?

Trip: Completely. We're enhancing the island. We donate to things.

Dee: What things?

Trip: [thinks] There's a... my mom went to a gala once. For the... it was for something. Boats? Boats or birds.

Dee: Do you know anyone who lives here year-round?

Trip: Our caretaker.

Dee: His name?

Trip: [long pause] He's Portuguese. Very nice.

Dee: Last question. What would you say to someone who thinks you're not really a local?

Trip: I'd say come to Cisco Brewers any Saturday and watch me. I'll know at least... [counts on fingers, runs out of fingers, starts over] ...several people there. By name. First name. And that's what community is.

Dee: I think our time is up.

Trip: Already? [checks phone] Oh—my dad just landed. I have to go wait for him at the FBO. Shouldn't be more than an hour. [sighs heavily] This island, I swear.

[As Trip left, the hostess informed me he'd put our drinks on "the Whitmore account," which apparently hasn't been paid since March. I covered the check. It felt thematically appropriate.]