Watkins' father, Todd, is a road grader. In high school, Watkins played rugby and hockey as a defenseman, but became the "designated goon" because of his size. He became a junior firefighter when he was 16 after visiting the West Kelowna Fire and Rescue .
Watkins enrolled at Butte College to study fire sciences in order to become a firefighter after a year as a junior firefighter. The school's football coach recruited him to play for their football team, at the age of 22. He played football at Butte from 2007−2008, helping them to a perfect 11−0 record in 2008. Butte coaches sent game tape of his to Division I-A schools, and California, Hawaii, and Baylor were the schools interested.
Watkins invited five of his friends from the West Kelowna fire department to join him at the draft. On the morning of the draft, Watkins and his firefighter friends visited a New York City firehouse that lost several members during the September 11 attacks.
Watkins was selected with the 23rd overall pick by the Philadelphia Eagles in the 2011 NFL Draft. He became the oldest first-round selection since 1980 at the age of 26. He was the first Canadian to be drafted in the first rounds of both the CFL and NFL drafts since Mike Schad in 1986. He was projected to start as a rookie at right offensive guard and signed a four-year contract worth $7.9 million on August 1. However, the Eagles claimed Kyle DeVan off waivers from the Indianapolis Colts before the start of the season and Watkins was benched. Watkins was inactive for the first two weeks of the season and was active for a week three game against the New York Giants, but did not play. He was inactive again in week four, but was promoted to the starting right guard on October 5, due to the ineffectiveness of DeVan through the first four games of the season. Watkins was released on August 31, 2013. Eagles general manager Howie Roseman said the “innate toughness” Watkins showed at Baylor never materialized.