OF the five members of a purported crime ring who appeared in court last month, Jennifer Sultan could not help but stand out. She seemed to have little in common with those said to be her accomplices: among them, a police officer charged with stealing his colleagues’ guns to support a painkiller habit and two unemployed young men from Brooklyn and Queens charged with selling guns and drugs.


The prosecutor, who opposed bail for most of the defendants, pointed out to the judge in State Supreme Court in Manhattan why each one might be a risk for flight. When it came to Ms. Sultan, 38, every head in the courtroom swiveled at the main point: she had once been a dot-com millionaire.


The finer details were not mentioned that day: at the high-water mark, she and her boyfriend were co-founders of a small Internet company that sold for $70 million. They rented a summer house in the Hamptons for $400,000. They bought a 6,000-square-foot loft on East 17th Street just off Fifth Avenue.


Now, a little more than a decade later, Ms. Sultan is bankrupt and sitting in a jail cell, unable to pull together $85,000 for bail. If convicted, she faces 15 years to life in prison on charges of selling prescription painkillers to an undercover police officer and of trying to sell a .357 Magnum to the man accused of being the ringleader.


Her life has in some ways followed the arc of her times, with even more extreme swings.


She rode the euphoria of the late-1990s technology stock boom to apparent riches at age 25, saw those fortunes collapse with the stock market in the early 2000s and was unable to stage a comeback in the more sober recession era.


To some who have known Ms. Sultan, her overwhelming ambition and dalliances with wilder crowds as a young adult in Manhattan made her fall less surprising. But to others, including her close family, the collapse has been bewildering.


“We are treading on water that we have never treaded on before,” said her mother, Brenda Sultan. “She is such a sweet, thoughtful person.”


She grew up as the middle child between two brothers in West Long Branch, N.J., five miles north of Asbury Park. Her father, David Sultan, owned a dry-cleaning business. Her mother had grown up in Brooklyn and dreamed of an idyllic suburban life for her children. They lived that life in a modest colonial-style house at the end of a quiet cul-de-sac.


Her mother recalls the terror of watching Jennifer, at just 2 years old, perched at the end of a diving board over the deep end of a swimming pool.


“Everybody, look at me!” she shouted as she leapt.


That physical confidence evolved into athletic prowess when she was a student at Shore Regional High School. Jennifer excelled in five sports: soccer, field hockey, softball, swimming and diving.


“She was tough,” Mrs. Sultan recalled. “She is, in fact, a girlie girl, but she’s also very athletic.”


Young Jennifer filled stacks of journals with her thoughts and dreamed of writing children’s books. In her senior year of high school, she smiled confidently in her yearbook above a long passage she had written.


“Like a small child I climb up the stairway of life. Have I come to the end or have I only just begun?” the text began. “My collected visions have enabled me to keep dreaming. I must go now, my life awaits.”


FOR Ms. Sultan, the city that her mother had left behind held great allure. She was accepted to New York University, her first choice, where she studied literature.


“She just fell in love with the city, and N.Y.U. was a fabulous opportunity for her,” her mother said. “She did extremely well. She blossomed in college.”


She became interested in photography and while still in college parlayed that into freelance work taking pictures of rock stars, including David Bowie and the members of Aerosmith, in posed settings and during concerts, according to her mother and a business associate.