agonize

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Although the decision to fire him agonized Giles, eventually he realized he would never be able to turn the vice president into a team player.
In April 2001, we learned that Jean-Bernard had amyloidosis and in the next months agonized as his condition grew worse.
In recent months, Britain has agonized over the massacre of 16 schoolchildren and their teacher in Dunblane, and the fatal stabbings of 12-year-old Nikki Conroy in her classroom and of London headmaster Philip Lawrence by a pupil.