The Sad Saga of Bob Greene

When a woman from his past resurfaced, the columnist’s 33-year career crashed; then a family tragedy hit home.

(page 12 of 15)


Most of the stories that circulated were more like the one reported to Chicago by Barbara Crystal, a 46-year-old corporate communications professional. Crystal first visited Greene when she was a 17-year-old senior on an assignment for Sullivan High School, during the 1973-74 school year. They met in the Sun-Times reception area and spoke for 30 minutes, and Greene was “a perfect gentleman.”

Four years later, in 1978, Crystal, then 21, spotted Greene at a Rush Street bar. She recalls that he said, “Oh, please have a drink with me.” A few drinks later, they moved-at Greene’s suggestion-to the bar at the Continental Plaza Hotel (now the Westin). “He started giving me lines about how his wife doesn’t understand him,” Crystal says, “how he has an unhappy homelife and lives at the hotel.” He invited her up to a room. It was 2 a.m. Once they got there, she kept the door open and her coat on. She says that Greene then got “a little handsy with me and I realized this wasn’t where I wanted the evening to go.” She bolted.

Megan Sheppard, now a 43-year-old writer living in Seattle, had another kind of encounter with Greene years later. She sent him a fan letter around 1987, mentioning that in a recent personals ad she had described herself as a Bob Greene fan; she thought he would be amused by that. About a week later, Greene called. He never suggested they meet or brought up sex. “It was a lot of chitchat,” she says. “But before long it became very apparent that what he really wanted to do was ply me for more information about why he was so wonderful.”

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By the mid-nineties, Greene’s popularity seemed to be on the wane. The number of papers buying his column began to plummet, dropping from the 1988 peak to about 100 last year-a decline that coincided with a falloff in demand from newspapers for syndicated general interest columns. There were rumblings again that some inside the Tribune wanted to move Greene off the front page of Tempo, although the paper’s editors have always denied that.

Greene was held in particularly low regard by many other Chicago journalists. From 1995 to 1996, the Reader ran “Bob Watch,” a witty and biting weekly feature written under a pseudonym by Neil Steinberg. The column examined Greene’s output under the slogan “We read him so you don’t have to.”

Within the Tribune, Greene had fewer allies than ever. Colleen Dishon, the powerful associate editor who had reinvented Tempo and who had always squashed features department rebellions against Greene, had retired. Squires had left the paper. And Paul Galloway, with whom Greene had been friends since his Sun-Times days, retired in 1999. “Once Galloway retired,” says a former Tribune colleague, “I’m not sure Greene had a friend in the building.”

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