Gladstone began coaching in 1966, directing the Princeton University[5] freshmen to a pair of silver medals at the Intercollegiate Rowing Association regatta, also known as the IRA.
[9] Gladstone retired after the 1980 season[3] and coached the Cal Alumni for one race in 1981—winning the San Diego Crew Classic.
[3] Gladstone's tenure as athletic director included the hiring football head coach Jeff Tedford.
In 2010, Gladstone left the CRC to assume the head coaching position for the Yale University heavyweight men.
His efforts began to bear fruit during the 2014–2015 season, with a first-place finish at Eastern Sprints (the first for Yale since 1982), a win over Harvard in their annual head-to-head race (the first since 2007), and a win over five-time national champion University of Washington at Henley Royal Regatta in the final of the Ladies' Challenge Plate.
In 2017, Yale went on to capture its first IRA varsity title by defeating the University of Washington at Lake Natoma by 0.069 seconds.
In 2019, Yale captured its third IRA varsity title by defeating the University of Washington at Lake Natoma by 3.14 seconds.
[11] Gladstone has served on the board of directors of the National Association of Amateur Oarsmen and has also been a member of the Men's Olympic Rowing Committee.
Including his tenure at Cal, Brown and Yale, Gladstone's boats have won 14 IRA titles in the varsity event, tied with Charles E. Courtney of Cornell who coached from 1883 to 1920.
During his career at Harvard, Cal, Brown and Yale, Gladstone's first boat has officially won the conference championship a remarkable 18 times.