Jerry attended South Panola High School in Batesville, Mississippi, where he was a two-way lineman and his career totals included 205 tackles, with 13 quarterback sacks. As a senior, he made 88 tackles, including five quarterback sacks, and returned one pass interception for a touchdown. He helped lead South Panola High School and coach Ricky Woods to a 44-1 record, including state championships in 2003 and 2004, while being runners-up in 2002. Considered a three-star recruit by Rivals.com, Jerry was listed as the No. 27 offensive tackle prospect in the nation.
College career
After a prep school year at Hargrave Military Academy, Jerry started all 12 contests at right guard for the Ole Miss Rebels in 2006. He was honored by several postseason publications as one of the top freshman linemen in the country, including The Sporting News and Rivals.com. In 2007, he played in all 12 games and started nine at the right guard position. Jerry was moved to right tackle and started all 13 games at the position in 2008, and earned second team All-SEC honors from the SEC Coaches and Phil Steele. In 2009, Jerry was listed at No. 5 on Rivals.com′s preseason offensive tackle power ranking. He was also named to the 2009 Outland Trophy watch list.
Professional career
Jerry was considered one of the better offensive linemen available in the 2010 NFL Draft. He drew comparisons to Leonard Davis. On draft day, he was selected by the Miami Dolphins in the third round with the 73rd overall pick.
Miami Dolphins
In February 2014, the NFL released the "Wells Report" finding that Jerry, along with Dolphins teammates Richie Incognito and Mike Pouncey, had bullied and harassed lineman Jonathan Martin, another unnamed player, and an assistant trainer during the 2012-13 seasons. The harassment of the assistant trainer, in which Jerry took part, included racial insults.
On March 21, 2014, Jerry was signed by the New York Giants. On March 13, 2015, Jerry re-signed with the Giants. On March 13, 2017, Jerry signed a three-year, $10 million contract extension with the Giants. He started all 16 games for the Giants at right guard in 2017. On September 2, 2018, Jerry was released by the Giants.
On June 10, 2019, Jerry signed with the Cincinnati Bengals. He was released during final roster cuts on August 31, 2019, but was re-signed two days later.