Leary did not start playing organized football until his junior year at Southern University Lab High School, where he earned All-State and All-District honors.

The next year, he was named the starter at left tackle, where he would remain for the most part of his college career, while making 36 consecutive starts.

During his senior season, he underwent surgery in May 2011 to repair a torn meniscus in his left knee, but didn't miss any games.

He ended protecting three different quarterbacks, while starting the first six games at left tackle, before switching to right guard when injuries impacted the offensive line.

Leary was not selected in the 2012 NFL draft because of a degenerative left knee condition (osteochondritis dissecans)[1] which could potentially shorten his career.

[8] He was getting first-team reps at left guard ahead of an injured Nate Livings, before needing arthroscopic surgery on his right knee during preseason.

In 2014, he earned the left guard starting role over Mackenzy Bernadeau and was a part of arguably the best offensive line in the NFL.

He started in the last game against the Washington Redskins in place of an injured Collins, but left in the third quarter after suffering a concussion and was replaced by Mackenzy Bernadeau.

[16] He suffered a concussion in the fourth quarter against the Cleveland Browns and he did not play in the last game of the season due to a back injury.