John Gregory, who guided the Saskatchewan Roughriders to their second Grey Cup title in 1989 had an estimated net worth of $2 million at time of death.
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Gregory coached college football and at the professional level in the Canadian Football League (NFL), Arena Football League (AFL), and Indoor Football League (IFL).
His first coaching job was at Iowa Central Community College, where he was assistant head coach and athletic director of the new football program.
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In his three years there, the program had a 24–3–1 record and won the Wool Bowl in 1969.
Gregory’s first college head coaching job was at South Dakota State, where he had 55–50–3 record from 1972 to 1981.
He places third in the school’s history in coaching victories.
More so, his 1979 team had a single season best record of 9–2.
It is worth noting that eleven seasons prior to his arrival, SDSU didn’t have a winning record.
Gregory was born on November 22, 1938 and died on December 12, 2022 at age 84.


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