Cleveland Browns The
Cleveland Browns selected Gregory in the ninth round of the
1966 NFL draft, 139th overall. The
Buffalo Bills selected Gregory in the first round of the
1966 AFL redshirt draft, 9th overall. After another year of college at Delta State College in 1966, Gregory chose to sign with the Cleveland Browns before the 1967 season. Wiggin retired before the 1968 season and Glass was injured during that season. Gregory filled it at both defensive end positions in 1968, starting six games. He had 3.5
quarterback sacks that season. The Browns won their division that season, and then defeated the
Dallas Cowboys in the
divisional round of the playoffs, 31–20. Gregory started that game at left defensive end and had one sack. He also started at left defensive end in the
1968 NFL Championship Game, a 34–0 loss to the
Baltimore Colts. In 1969, Gregory started all 14 Browns' games at right defensive end. He had a team-leading 11 quarterback sacks, along with one interception and one fumble recovery. His 11 sacks were tied for seventh best in the NFL that season. He was selected to play in the Pro Bowl for the first time in his career. The Browns had a 10–3–1 record, winning their division. The Browns lost the
1969 NFL Championship Game to the
Minnesota Vikings, 27–7, though Gregory had another sack in that game. Gregory started all 14 games at right defensive end again in 1970. He had a team-leading 15.5 sacks on the season, and was second in the NFL in most sacks that year. He also had one fumble recovery. It has also been stated that he had 14 sacks in 1970, the second most in Browns history for a season (as of 2005). Bill Glass unofficially had 16 sacks for the Browns in 1960. In 1971, Gregory again started all 14 games as the Browns' right defensive end, with a team-leading 8.5 sacks. He again had one fumble recovery.
Playing out option Gregory did not sign a new contract with the Browns going into the 1971 season. He said in July 1971 that if the Browns and he did not agree to a new contract, he would play out his option and then go to another team. Playing out his option would make Gregory a free agent at the end of April 1972. However, under the NFL's
Rozelle Rule any team signing him as a free agent would have to compensate the Browns with a player and/or draft picks; which compensation could be determined by NFL commissioner
Pete Rozelle if the old and new teams could not agree. Gregory became the first Brown ever to play out his option. Gregory had an agent by 1972 (Ed Keating) who was negotiating with the Browns to potentially stay with the team. A few days after Gregory became a free agent in early May 1972, and the negotiations were faltering, Browns' owner
Art Modell was reported as saying "I feel it's absolutely insane for a player who has dealt with us to use an agent". Gregory later said that while financial issues were his principal consideration in choosing to leave the Browns, there was also some "personality conflict" between him and Browns' head coach
Nick Skorich and it was time for a change. Gregory and Keating were interested in six teams, and two others approached them. They ultimately reduced their interest to the
New York Giants,
St. Louis Cardinals and the
Oakland Raiders. In mid-June 1972, it was reported that in separate transactions on the same day (1) Gregory signed with the
New York Giants as a free agent, and the Giants and Browns agreed the compensation would be a 1973 number one draft choice; and (2) the Browns traded
Freddie Summers to the Giants for a 1973 number two draft choice. The first-round pick was later used by the Browns to select
Steve Holden and the second-round pick used to select
Greg Pruitt. In his final NFL season, the 35-year old Gregory started 11 games for the Browns at right defensive end, with 2.5 sacks and one fumble recovery. In January 1980, the Browns chose not to re-sign Gregory. During his six years with the Browns, Gregory started 62 games with 41 sacks, five fumble recoveries and an interception.
New York Giants In 1972, under defensive coach Jim Garrett, the Giants adopted a defensive scheme that used Gregory as a "rover" on defense. Under this system, modeled on the
1967 Oakland Raiders' defense, Garrett kept three Giants' defensive linemen stationary, while allowing Gregory to play multiple positions across the defensive front, including anywhere on the defensive line or at linebacker. Garrett chose Gregory as the Giants' rover because he believed Gregory was a great athlete who had the inherent natural ability to be an excellent pass rusher. The Giants were confident in Gregory, and allowed him to make his own decisions about where to position himself on defense as a rover. Gregory started all 14 games for the Giants and unofficially led the NFL with 18.5 sacks (sacks not becoming an official statistic until 1982). He was also said to have had 21 sacks in 1972. He was selected to the Pro Bowl for the second time. The Giants' record went from 4–10 in 1971, to 8–6 in 1972. In 1971, the Giants had only 18 sacks as a team and allowed 362 points, whereas in 1972 the team had 37 sacks and allowed only 247 points. The Giants ceased using the rover defense entering the 1974 season under new head coach
Bill Arnsparger, who had just won
Super Bowl VIII as defensive coach of the 1973 Miami Dolphins. Arnsparger stated in March 1974 that he saw Gregory as a right defensive end, not a rover. Arnsparger hired
Floyd Peters as his defensive line coach. The Giants record fell to 2–12 in 1974. Gregory started 14 games at right defensive end, with 9.5 sacks that year. In 1975, Gregory again started all 14 games for the Giants at right defensive end. He had 14 sacks on the season and one fumble recovery. The Giants improved to 5–9. The Giants credited him with 15 sacks that season. He was the Giants most valuable player and the team's defensive player of the year in 1975. The Giants fired Arnsparger after losing the first seven games of the 1976 season, replacing him with
John McVay, who led the team to a 3–4 record to finish the season. Gregory was a team captain in 1976. He started 11 games with 4.5 sacks that season. Gregory played two more seasons for the Giants (1977 and 1978), starting all 30 games at right defensive end. He had 7.5 sacks in 1977 and 2.5 in 1978. He also had one forced fumble and three fumble recoveries during this period. In early August 1979, Gregory left the Giants training camp, asking to be traded. The Giants traded him to the Cleveland Browns. == Legacy and honors ==