The New Canaan Darien Magazine has an interesting article/interview with Cashman:

“My father broke every child labor law,” Brian says with a shake of his head. Cleaning stables, he says, “gave me a work ethic and made me realize how tough it was to get by.” It also gave him a profound distaste for horses. He preferred basketball and baseball. His favorite baseball team was the Los Angeles Dodgers. Brian rejoiced when they beat the Yankees in the 1981 World Series.

“At that time I was one of the all-time Yankee haters,” Cashman admits.

Fate was about to play a funny trick on him. At a racetrack his father managed in Florida, the publicity director, a man by the name of Allan Finkelson, was a close friend of a horse-racing enthusiast named George Steinbrenner. While Brian was in college, Finkelson landed him a Yankees internship. ...

When she worked as a player agent, Jean Afterman clashed with Cashman over the contracts of players like Hideki Irabu and Alfonso Soriano. Yet Cashman was impressed by her tenacity. “She was so sharp and tough in negotiations, I always had it in my mind that I wanted her on our side of the fence,” he says. He hired her as assistant general manager in 2001.

“Brian is uncomfortable with the nice things you say about him, but those same qualities come through whichever side of the fence you’re on,” she says. “He has a strong sense of integrity, what’s right and wrong. If there’s a misunderstanding, there’s no ego involved. That’s one of the most significant things about him. He’s confident, and he should be. He has nothing to prove. Brian is very comfortable in his own skin.”

Jean Afterman is one of only three women to have held the position of assistant general manager in the majors. Two of those women — Jean and her immediate predecessor Kim Ng (now with the Los Angeles Dodgers) — were hired by Cashman. Keith Hernandez may not like them in the dugout, but Cashman is fine with women in the front office.

“It’s Brian recognizing the value and merit of somebody and being gender-blind about it,” Jean says. “A lot of men are not comfortable working with women, especially in sports. That’s not an issue with Brian.” ...

Cashman discusses the Boss with both humor and sensitivity. He recalls the first time he drove Steinbrenner around as a young intern and hit a pothole on the FDR Drive. “This isn’t a freaking tank!” Steinbrenner yelled, not exactly in those words. At the same time, he disagrees with those who portray Steinbrenner as a backseat bully. ...

Torre says Cashman reminds him of Dal Maxvill, a longtime St. Louis Cardinal GM for whom Torre worked. “He’s the same type of personality, where they can be calm and collected but have a rough edge to them,” Torre says. “When they get angry, they let you know. There’s nothing Brian’s going to keep inside.”

Via Steve.