Strief attended Northwestern University in Evanston and redshirted his first year. By his junior season he became starting right tackle for Wildcats and started in 40 straight games under Mike Dunbar, who was the Wildcats’ offensive coordinator. He earned consensus Second-team All-Big Ten honors twice and was named an All-American by the FWAA during his senior season, becoming the Wildcats’ first offensive lineman to win national recognition since Chris Hinton. NFLDraftScout.com described him as a “hard worker who has no problems digesting a complicated playbook.” He graduated with a degree in communication studies and sociology in 2005.

A native of the Cincinnati suburb of Milford, Strief attended Milford High School and earned All-Midwest Region honors with the Eagles football team. Besides football he also earned varsity letters in basketball and track and field. He was also an honor student. In January 2009 Milford High announced to it would retire Strief’s number 63 jersey (which he also wore in college), only the second jersey to be retired by Milford.

Since moving to New Orleans, Strief has set up a foundation which organizes youth camps and aids Milford student-athletes. In 2009, he produced a cookbook for charity entitled When You’re the Biggest Guy on the Team!

He was drafted by the New Orleans Saints in the seventh round of the 2006 NFL Draft. After backing up Jon Stinchcomb for five years, in the 2011 season he became the team’s starting right tackle with Stinchcomb’s retirement and part of the Saints’ offensive line that won the Madden Most Valuable Protectors Award as the best offensive line in the NFL. (He also shared in the same award as a backup in 2009.)

Strief re-signed with the Saints on a five-year extension during free agency in 2014. This is the second time he re-signed in free agency.

In 2017, Strief suffered a knee injury in Week 1 against the Minnesota Vikings and missed the next two weeks. He returned in Week 4, only to re-injure the knee and was placed on injured reserve on October 3, 2017.

On March 12, 2018, Strief announced his retirement from the NFL.

On July 25, 2018, Strief was named as the play-by-play voice announcer for Saints radio broadcasts, replacing the retired Jim Henderson. Strief works with color analyst and former teammate Deuce McAllister on the broadcasts.