Eva Brann was never quite sold on the idea of an afterlife.

Her friend, Grace Cavalieri, disagreed. So, toward the end, they made a bet: If there was an afterlife, Brann would buy lunch. If there wasn’t, it was Cavalieri’s responsibility. Brann, a philosopher, was keen on the idea, “because in philosophy, 50/50 is an acceptable proposition,” her friend said.

Brann, the longest-serving instructor at St. John’s College in Annapolis and the recipient of a National Humanities Medal, now knows the answer, wherever she may be. She died on Oct. 28 of natural causes at the age of 95.

Brann was born in Berlin in 1929 to a German Jewish couple. When she was 12, as the threat of Nazism grew, she and her family left for Portugal, where they then set on a path to the United States. She first landed in New York, where she attended Brooklyn College and read “The Iliad” by Homer for the first time.

She was so intelligent that she could have been anything, Cavalieri said. But Brann saw her future in the epic poem: “It was golden,” Cavalieri said. “That’s all she could say. She wanted nothing else.”

Brann then attended Yale University to earn her master’s degree in classics and a doctorate in archaeology. She briefly taught archaeology at Stanford University before interviewing for a job in 1957 that would change the direction of her life: a professor at St. John’s College in Annapolis. There, instructors are called tutors because they guide discussions instead of giving lectures.

She was one of few women in a male-dominated field and college. Cavalieri said it was almost like Brann didn’t know she ever faced discrimination — “she was equal to every man, and she knew it.”

“If she were a man philosopher, she’d be a household term,” Cavalieri said. “She was the greatest philosopher of our time.”

Brann’s dedication and intellect made her a clear candidate for dean, which she achieved in 1990. It was around this time that she met Christopher Nelson, who served on the college’s Board of Visitors and Governors and became president of the college in 1991. For six years, the two had offices right next to each other.

“She kind of raised me up,” Nelson said. “I listened carefully and tried to learn. I suppose, without ever being in a classroom with her, I was very much the student, and she, the teacher, in those days.”

Brann loved being around the other tutors and students at St. John’s, and she earned a reputation for the “mischievous twinkle in her eye” that set her apart from other scholars, Nelson said. She was always enthusiastic in meetings and discussions with others, he said.

When you looked into her eyes, you would often see “a woman of great wisdom who was just having loads of fun with whomever she was talking,” Nelson said.

Nelson recalled the time students tapped Brann to play Yoda in a Star Wars skit. It was the perfect role, he said, and she expertly mirrored the character’s expressions and demeanor. Brann didn’t mind acting silly or performing tasks that might have embarrassed others, he said. Another time, the school hosted a circus-themed event, and Brann had no issue getting up on stage and taking a pie to the face, Nelson said.

Above all, Brann was a “philosophical soul,” Nelson said, that reflected her childlike wonder and curiosity about the world. She perfectly married innocence and inquisitiveness with “an incredible vocabulary and a way of capturing the essence of anything,” he said.

It was that sharp ability to explain and connect with others that made her an exceptional tutor, said Janet Dougherty, Brann’s longtime friend.

“Her clarity of mind is what always stood out,” Dougherty said. “She was extremely articulate and made rather difficult material accessible to people. She was very attentive to where they were, to their thoughts and how they were expressing them.”

A student once approached Brann while she was dean of the college and told her she was thinking about dropping out, Dougherty recalled.

The student told her, “I want to make a difference in the world.” Brann didn’t ask her what she imagined doing or how that would make a difference, Dougherty said. Instead, she replied, “For the good?”

“The point was: Don’t you need to think about what the good is?” Dougherty said. “It just seems to me that’s just going right to the heart of the matter, without fussing around or getting distracted, and with complete respect for the dignity of the other person.”

That was part of the reason Brann loved living in Maryland and in the United States, Dougherty said. As a young woman, Brann briefly returned to Germany and realized that she much preferred the way Americans interacted — with decency and respect for each other’s differences.

Brann was “quintessentially American,” Dougherty said. On her 94th birthday, she requested meatloaf, mashed potatoes, baby peas and apple pie.

Brann leaves behind a long list of friends, colleagues, admirers and students who still ponder her poignant insights. Brann wrote many of them in more than 20 books she produced in her lifetime, which included reflections about famed philosophers and her own thoughts on happiness, feelings and free will.

Paul Dry, Brann’s publisher, said the philosopher was a special talent because her thoughts were evergreen and “always fresh.” She was open to endless possibilities.

“When asked a question, even about a matter she thought she’d settled in her mind, she would take it up afresh and [say], ‘Well, that is an interesting question,’” Dry said.

Perhaps that is why, as her health declined, Brann revisited the idea of life after death.

Toward the end, she had a recurring dream she would recount to Cavalieri: There was an angel at the concierge window of the afterlife, and she was waiting in line. By the time she approached the counter, the angel was asleep.

Cavalieri trusts she will see Brann again. Their friendship was too beautiful to leave here: “We really softened the earth for each other,” she said.

And when they are reunited, Cavalieri said, lunch will be on Brann.

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