Weight Problems
Gregg battled weight troubles throughout his career. His weight was generally listed between 315 and 325 pounds, but Gregg admitted that this was often an understatement and that he frequently approached 400 pounds. In 1996, fellow umpire John McSherry died in Cincinnati of a heart attack; the two had planned for a long time to try to lose weight together, but McSherry's death motivated Gregg to take a leave of absence from umpiring and enter a program at Duke University.
His frame, still hefty and recognizable despite the weight loss, encouraged publicity for Gregg. He was honorary commissioner of the Wing Bowl, an annual competitive eating event in Philadelphia, and also umped at various celebrity softball events. He also occasionally worked at Chickie's and Pete's Philadelphia restaurant and at the restaurant's stand at Veterans Stadium as a bartender and server. Aside from his girth, he was also well known for his jocular personality and wide smile, which had a disarming effect on game participants who took issue with his calls.
In 1999, he was fined $5,000 by the National League for exceeding a 300 pound weight limit.
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