Having no previous football experience, Jimmie Simpson tried out for the Hamilton Tigers (they would only become the Tiger-Cats in 1950) in 1928. Simpson was all of five foot six and 135 pounds of energy. Simpson played Outside Wing (End) and in his early years was tutored by the great hall of famer Cap Fear. Simpson would go on to play 11 years for the Tigers from 1928 to 1938, mainly in an era of no or little passing and where players went both ways for sixty minutes. It was also an era when it was not unusual for one player to haul off and punch someone. In his first game against Toronto, Simpson came away with a pair of black eyes from the opposing end. Simpson's career with the Tigers came to an end in 1938 when another punch broke his jaw in an exibition game that caused him to miss the entire season and he couldn't pass the medical in 1939. Football was still in Simpson's blood, however, and he took up coaching with a junior team and working as an official. In 1943, Brian Timmis, another former legendary Tiger asked Simpson to help coach the Wildcats of the ORFU (Ontario Rugby Football Union) and Simpson did one better, unretiring at the age of 37 to play two seasons for the Wildcats. Simpson would win his fourth Grey Cup with the Wildcats in 1943, adding to the three he won with the Tigers in 1928, 1929 and 1932. Simpson also was on the losing end in two Grey Cups, with the Tigers in 1935 and with the Wildcats in his final season in 1944. After finally retiring as a player, Simpson then resumed his officiating career and then went on to become the trainer with his beloved Tiger-Cats. Counting his time as an official and a trainer, Simpson participated in 19 Grey Cups in his career.
The first individual stats available for the East / IRFU / Big Four are from 1930 and only include scoring. Simpson had one touchdown in 1935 when touchdowns were worth only 5 points. In 1973, Simpson scored 2 points on safety along with 2 converts to account for his total of 4 points.
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