Tiger of the Week: Sean Gregory ’98

Published in the Nov. 19, 2008, Issue

Dressed in a T-shirt, basketball shorts, and a pair of boxing gloves he'd bought at a New York sporting goods store, Time magazine reporter Sean Gregory ’98 climbed into the ring with Oscar De La Hoya at the boxing champion's Big Bear Lake, Calif., training camp last week. Fortunately for Gregory, the encounter was a boxing lesson, recorded for Time.com, and not a revival of George Plimpton's participatory journalism. Viewers learned about a few of the sport's finer points, and the writer emerged without a scratch -- a win-win for Gregory, our Tiger of the Week. (De La Hoya was not as fortunate in his most recent fight; he lost a Dec. 6 bout to Manny Pacquiao.) Gregory, a Woodrow Wilson School major who graduated from Columbia University's journalism school in 2002, may be a familiar face for Princeton basketball fans. He was a reserve guard for the Tigers during a memorable run of Ivy championship seasons from 1996 to 1998. But an athletic background did not make Gregory a quick study in the boxing gym. His fumbling attempt to find his tempo on the speed bag offered a stark contrast to the mesmerizing rhythm of De La Hoya's punches. That part was not scripted, Gregory said: "I actually was trying."