The last thing Barack and Michele Obama did before leaving the Vineyard last summer was to have dinner at the Red Cat Kitchen on Kennebec on the way to the airport.

Their first dinner out after returning to the Island this weekend was at the Cardboard Box across the street on Circuit avenue.

Custom Cardboard Box logo created by Island artist Traeger DiPietro. — Jeanna Shepard

Both Oak Bluffs restaurants are owned by chef Ben deForest. If the Red Cat is like a comfortable, well-worn leather jacket — cool and confident — the Cardboard Box, which opened in May in the former Down Island restaurant space, is more like a shiny new pair of shoes.

If you were the ex-POTUS, eager to relax with good friends (belatedly celebrating your birthday) and to enjoy a meal of really good, really satisfying food, you might take the easier route and slip in the back door of the Red Cat, where a small private dining area makes enjoying a quiet meal effortless. The Obamas ate there twice last summer.

Instead, the Obamas decided to gather a group of 12 friends at Ben’s newest venture.

“That was the gracious, amazing thing that happened last night. That’s what really moved me,” Ben told me the next day. “They could have gone to the Red Cat, but instead they lent their influence to a business in its first year. They know this is our opening year. That wasn’t lost on me and it blew me away.”

What blew me away (I was there on Monday night) were two things: what came out of the kitchen and what I found on the street when I left the restaurant.

Maybe you remember that I happened to be a fly on the (kitchen) wall last summer during the Obamas’ pre-flight dinner at Red Cat. I happened to be working on a story about Ben and had just about wrapped it up when the opportunity to hang behind the scenes on a busy Saturday night in August with the former first couple in the house happened to come up. Well, this year I happened to be looking for the right time to write about the Cardboard Box (while working on a completely different story this week for Off the Menu) when I just happened to find myself on a barstool at the Box Monday night. Okay, that’s not entirely true — all of that didn’t exactly just happen (enough already with the happenings, I hear you say). If you think I am being a little facetious, you might be right; just the idea of me happening to be on a barstool is a laugh. A lot of things happen on this Island if you keep your ear to the hot pavement in August, but that is all I have to say about that, as Forest Gump would say.

What is true is that I’ve been genuinely curious about both the food and the experience at Cardboard Box since I got a peek at the big space when Ben was working on it in late spring and then went for a quick dinner after he and his wife Erica DeForest (they are co-proprietors on this venture) first opened. The menu was ambitious, the vibe was electric, but the new shoes were still a little tight. Knowing that Ben’s restless drive would keep the restaurant evolving over its first few months, I waited to come back.

When the president comes for dinner . . . . a thank you note is in order. — Jeanna Shepard

Monday night, while the Obamas and their friends dined in the enclosed porch (the area directly under the Lampost balcony) with police and secret service positioned outside to manage what turned out to be a huge crowd gathering for a chance to see the former president, my dinner companion and I had a delicious, relaxed meal. Al Green sang Let’s Stay Together on the sound system, our bartender Jacob Wolfe offered just the right amount of menu information and attentiveness (no small feat with all of the 35 seats at the bar occupied by a diner, and every other occupied seat in the restaurant ordering drinks that include house specialties like The Midnight Swim and the Kharma Chameleon), and the kitchen fired one hit after another.

The kitchen is fortuitously manned (and woman-ed) by an ace team. Hannah Flora-Mihajlovic and Dominic Giardini were the lead cooks in chef Scott Cummings’ Down Island kitchen, so not only are they familiar with this particular kitchen, but they also bring their strengths and experience to what Ben calls a collaborative effort. With Max Rodegast coming over from Red Cat to be chef de cuisine (or as the menu says of him: “He’s the Ballgame, Apple Pie, and a Fenway Frank. The Good Neighbor.”) and the team rounded out with Nick Berntson also in the kitchen and Caroline Derrig as general manager, Ben does not have to be behind the stove every night.

And that’s how he wants it to be.

“One of the really cool things that’s happening here is there is a tremendous amount of great input from the guys in the kitchen. They’re just rock stars,” he says.

“I’m not cooking very much in either place. If I was cooking all the time at Red Cat, this wouldn’t develop in the way that I want it to as a business. And if I were cooking over here, we’d risk homogenization of the food. So by taking a well-trained staff over at Red Cat — guys I’ve been bringing up for years — and letting them run with it over there, and then having all these guys over here who are so incredibly good — that’s the genius of evolving concepts that don’t revolve around me.”

The concepts may still be evolving — in fact they will always be evolving. To keep things interesting and seasonal, Ben has always embraced an updated daily menu at the Red Cat; this year they’ve printed 62 versions. While the Cardboard Box has updated 11 times this summer, there’s a solid chunk of the menu — most notably the Reliable Chop Board where the New York Strips and high-dollar Tomahawk rib-eyes live — that will stay grounded.

Food and experience at Ben deForest's new restaurant are both evolving. — Jeanna Shepard

In an effort to bring a good steak place and a lively menu (parts of which are available to late night diners until 12:45 a.m.) to Oak Bluffs, Ben spent the last couple of years “studying steak house culture” and trying to create a menu with broad appeal, a menu for everyone who wants to go out and have a good time and enjoy good food (as opposed to foodies looking for the ultimate dining experience). He describes the cuisine at Cardboard Box as “the Martha’s Vineyeard dream infused with aspects of steak-house culture.”

My meat-loving dinner companion was a good sport as I ignored the steaks and proceeded to order a bunch of starters for us to share, most of which had tomatoes in them. Ben (a self-described “tomato practitioner”) has a particular affinity for tomatoes and with the season just on us (I saw a big flat of Ghost Island Farm beauties in the kitchen), I wanted to dive into the tomato possibilities. Island farm heirloom tomato soup with sharp cheddar toast was my first choice, followed by marinated baby heirloom tomatoes with small batch feta, yellow curry oil and sweet onion vinegar syrup; they were joined by the hook-up romaine wedge salad with ranch dressing and the tempura Gulf shrimp with yuzu-Thai chili and pea shoots. We also split a main-dish order of one of Dominic’s special pastas; this one was linguine with lobster tail in a fresh pomodoro sauce with fresh corn.

After dinner, as reluctant to leave our seats as the rest of the restaurant diners who were hoping the Obamas might make a trip back through the big room to the kitchen before leaving, we stretched the evening out with one of Erica’s amazing desserts. Erica is better know as The Tiny Baker, and while we were eating a Key lime trifle with buttery graham crackers, she was plating a special birthday dessert for Mr. Obama — a “baker’s palette” ringed with treats, including chocolate Legos, meringue mushrooms, a slice of chocolate oreo cheesecake with a chocolate dipped strawberry; house made ricotta with lemon juice, Goldbud peaches and honey; a cake ball and a scoop of house vanilla bean ice cream with an edible messenger man happy belated birthday card. (The messenger man is the Cardboard Box logo created by Vineyard artist Traeger DiPietro.)

Ultimately, we had to go, but on the way out to our car on Kennebec, we decided to circle around to the front of the restaurant on Circuit to see what was going on. We knew that the street had been partially blocked off, but had no idea how large the crowd had grown.

As we stood there, it just kept growing, people pooling at the foot of the street near the information booth and streaming down from Back Door Donuts and the park at the other end. It seemed like there was a magnetic energy coming out of the Cardboard Box pulling everyone down the street. Families with kids on their shoulders and cell-phone cameras held high waited excitedly until the former president finally appeared on the sidewalk and waved. Cheers erupted and echoed up and down Circuit avenue as a jolt of collective energy surged through the crowd, through the town, and perhaps over the Island for all I know. It was an outside-the-Box kind of night.