Montgomery attended Centreville High School in Clifton, Virginia and was a letterman in football, basketball, and baseball.

[9] Although he became the starting center, he was moved to left guard after Kory Lichtensteiger suffered a torn ACL in Week 6.

[10] In Week 9 against the San Francisco 49ers, Montgomery moved back to center after Maurice Hurt took over as left guard.

Originally scheduled to be an unrestricted free agent in the 2012 season, Montgomery was re-signed by the Redskins to a four-year, $12 million contract.

[14] In the Week 13 game against the New York Giants, Montgomery jumped into a pile-on in an attempt to recover the ball that Alfred Morris fumbled.

On March 14, 2014, the Redskins informed Montgomery he was being released, saving the team $1.92 million in salary cap room.

[19][20] Montgomery started the final 8 games at center, helping Denver rank 8th in rushing yards (1,032) in the second half of the season.