Jeffrey was born in Yorkville, Illinois. After United turned him down, he applied to American; he was ecstatic when he was accepted on his second try.

His on-the-ground passion was tennis. The week before his death, he attended the United States Open in Queens. Jeffrey was an aspiring chef with a love of preparing dessert dishes and enjoyed flying for his work. He received the American Professional Flight Attendant Award in 1999.

Though he usually worked on only Boston-to-San Francisco flights, an itinerary that linked two of his favorite cities and made for a reasonable commute home to Navato, Califfornia, Jeffrey had switched to Flight 11's Boston-to-Los Angeles route for the month of September because of vacation plans involving his upcoming birthday. He had in fact a birthday coming up on Sept. 28 and signed on for the extra trip so that he could take time off to turn 42 with a little party at home.

Jeffrey had lived in Novato, California for the last four years with his partner, Keith Bradkowski. Jeffrey had spoken to Keith on September 10, saying he was excited about his vacation. He was working at his loved job when American Airlines Flight 11 was hijacked and then smashed into the first World Trade Center tower. Keith, his partner of 11 years, has become a spokesperson of sorts for gay rights and same-sex partner benefits since his spouse's death.