Selected by the
New York Giants with the tenth overall pick in the
1959 NFL draft, Grosscup appeared in eight games in his two seasons with the Giants. After being waived by the Giants, in August
1962, his contract was purchased for $100 by the second-year
Minnesota Vikings, but he was cut before the beginning of the season. This allowed Grosscup to return to New York in September, this time with the
New York Titans of the
American Football League (later known as the New York Jets), in its
third season. He began the season as the starter, but missed six weeks with a knee injury. Grosscup was cut on the final day of the
1963 preseason and signed with the
Saskatchewan Roughriders of the
Canadian Football League three days later. That same year, Grosscup released his first book, entitled
Fourth and One. After failing to make the
San Francisco 49ers, Grosscup spent the 1964 season on the
Oakland Raiders'
taxi squad. While skilled as a quarterback, Grosscup had the artistic temperament of a poet or writer, rather than the hard-bitten or violent temperament typically associated with professional football at the time. Before joining the NFL, he held a public written correspondence about football with a sportswriter. While popular generally, Grosscup came off as arrogant to his future Giants teammates, who originally isolated him when he joined the team and where he remained on the fringes of the team's players throughout his two years there. Giants coach
Allie Sherman disliked Grosscup as a player and a person; and during his short stint in Minnesota, Grosscup infuriated coach
Norm Van Brocklin by using the word "deuce" instead of "two" when calling a play, Van Brocklin telling him to use numbers as he did not go for "Madison Avenue stuff". After that, the Vikings players called Grosscup, Deuce or Madison. ==Broadcasting career==