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June 16, 2025

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1 Homepage Slider 3 Top Story

Profile: The Shore’s Johnny O’Brien and Milton Hershey’s School

September 3, 2014 by Dave Wheelan

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If the maxim that luck is the intersection of opportunity and preparation is true, long time Eastern Shore resident John (Johnny) O’Brien has had more than his fair share of stars lining up in his favor.

Shipwrecked, as it were, at the very outset of his life at the age of three, Johnny O’Brien arrived with his five-year-old brother, Frankie, at the Pennsylvania candy maker Milton Hershey’s legendary school for orphans under the worst of circumstances. After a family tragedy had taken away his parents under horrific circumstances, Johnny, as he notes in his interview with the Spy, arrived like “soiled laundry” by his aunt to an institution he would come to consider his home for the rest of his childhood and teen years.

From this remarkably tragic beginning, O’Brien would defy all odds and thrive at the Hershey School. Unlike his brother, who would succumb to a life of mental illness, Johnny moved on to Princeton University (where he currently serves as a trustee emeritus) and a successful career in CEO leadership training in Wye Mills. But unlike other success stories of this kind, the story doesn’t end there.

Over time, O’Brien would lead a successful alumni revolt against the Hershey School board of directors who had blatantly moved away from founder Hershey’s mission during the 1990s, and misallocation of the school’s huge $8 billion endowment. The uprising worked so well that it resulted in Johnny O’Brien, to his own shock, becoming president of the Hershey School in 2003. All of this he has captured in an extraordinary memoir titled, Semisweet: An Orphan’s Journey Through the School the Hersheys Built .

This video is approximately fourteen minutes in length. Mr. O’Brien will be the guest of the News Center in Easton on Saturday, September 6th starting at 10am. Later this fall he will be at the Bookplate in Chestertown.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 1 Homepage Slider, 3 Top Story

About Dave Wheelan

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Letters to Editor

  1. Gordon Bjorkman says

    September 3, 2014 at 5:15 PM

    What some of your readers may not know is that Johnny was a member of the 1964 undefeated Princeton Football Team. Johnny and his teammates will celebrate the 50th anniversary of the last undefeated Princeton Football Team at the Princeton Harvard Game in late October.

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