He attended Monte Vista High School in Danville,[1] where he played football as a flanker, cornerback and punter,[2] and was named the team's most valuable player.

[7][8] The Chargers had him rated as the top strong safety and 28th best player in the draft,[9] which was counter to the NFL trend of valuing a defender's coverage skills over their hitting ability.

[12] Later, the team wanted to add him to their active roster midseason, but he would have needed to be placed on waivers, which Coryell said would be too risky, believing another club would claim him.

[25] Chargers secondary coach Jim Wagstaff continued to suggest to Gregor that he curb his hitting intensity to reduce his injury risk.

"[26] In the season opener, Gregor and fellow safety Andre Young played a large part in forcing Denver into six turnovers.

[21] After Gregor appeared in just 23 games in three years as a starter,[1] the Chargers attempted to increase his availability by starting Miles McPherson in his place in 1984.

[21] Nonetheless, Gregor's season ended after he tore ankle ligaments in week 7 against Kansas City and was placed on injured reserve.

[30][31][32] After years of ranking among the worst defenses in the NFL, San Diego decided during the offseason to begin an extensive youth movement.

[33][34] Jerry Magee of The San Diego Union wrote that "the slightly built Gregor...played with a recklessness that was his own undoing.

The lawsuit stated that due to repeated head impacts during his NFL career, "Gregor has experienced cognitive and other difficulties including, but not limited to headaches, dizziness, loss of memory, depression, suicidal thoughts, sleep problems, and neck and cervical arthritis and associated numbness/tingling.

"[35] In 2015, a federal judge approved a settlement plan that could potentially cost the league $1 billion in payments to players over 65 years.