Jim Toole, who owned Capitol Hill Books for over 20 years and was affectionately known by staff and customers as “The Admiral,” died over the weekend, according to his family and colleagues. He was 86.

Toole, a former rear admiral in the U.S. Navy, purchased the bookstore from the original owner in 1995 and ran it until 2018 when he sold it to a group of his employees. He remained a full-time employee at the store and graced customers with his wit and curmudgeonly opinions on their book purchases and word choices.

He had plenty of rules — words including “like” and “perfect” were strictly banned on his “Not Spoken Here” list at the register — but, as former customers and friends shared on social media at the news of his passing, it was an honor to have Toole criticize your vocabulary or comment on the books in your bag.

“Once you walked into the store, he basically considered that you were boarding his ship,” says Kyle Burk, one of the four employees who bought the store from Toole. “That gave him the right to bark orders at you about where certain [book] sections were. It gave him the right to say, ‘You’re not allowed to say words like Amazon.'”

Toole was a wealth of information, Burk adds, and was known to recite poetry — including his own — or tell the history of one of America’s great naval battles.

“He loved to joust with people,” Burk says. “He lived for bantering with customers, and he loved for you to give it right back to him. That was why he worked at the store so long.”

On Saturday, the store held its monthly wine and cheese event, and Jim attended the event before going to dinner with friends. Following the dinner, he suffered a heart attack while walking to his car, according to his daughter, Laura Torres.

“What I’m really grateful for is that, in the hours before that, he was with a bunch of people that he loved, at a place that he loved, and with a community that he built,” Torres shared over a phone call Monday.

“It’s funny because he would sort of come across as this salty curmudgeon and a tough guy, but he could be very soft on the inside when you knew him,” Torres added.

We are sad to share that Jim Toole, owner of Capitol Hill Books from 1995 – 2018, has passed away.

Jim, AKA The Admiral, was still an active employee of Capitol Hill Books & will be dearly missed. He was one of a kind. pic.twitter.com/wpzFiyYic0

— Capitol Hill Books (@chbooksdc) November 13, 2023

One of Toole’s greatest traits, Burk says, was his generosity: The bookseller was always the first person to buy a round at their outings to local bars. He bought a laptop for a former employee who left to become a Peace Corps volunteer in Guatemala and sold his old Volkswagen station wagon to one of the co-owners for $1.

Always ready with a joke, Toole would tell the employees during front-desk shifts: “Okay, lad, you take the Con,” a ship command; or “fire when you’re ready, Gridley,” a reference to the Battle of Manila Bay.

Under Toole, the customer wasn’t always right — they were wrong until proven otherwise. But this spirit of debate added to the store’s character, and customers appreciated not being pandered to, Burk says. The store’s new owners, Aaron Beckwith, Matt Wixon, Shantanu Malkar, and Burk tried to carry on Toole’s legacy, something he appreciated. (Wixon passed away in 2019.)

“We’ve now been through two really tough deaths in the Capitol Hill Books family,” says Burk. “And books are our life. So as long as we’re here, the story is going to carry on. There’s nothing else that we’d rather be doing. We’ll carry on those memories with us and live in their spirit as best as we can.”

Toole is survived by his wife June, his daughter from an earlier marriage, Torres, and two grandchildren; three step-children, and five step-grandchildren. Capitol Hill Books plans to host a memorial event in Toole’s honor and will share details soon, according to Burk.