A two-sport letterman at Griswold High School in Griswold, Connecticut, Brackett played football and basketball. As a senior in 2008, Brackett was named First team All-Eastern Connecticut Conference as a quarterback. Brackett was a Class M All-Academic selection as a senior in 2009 on the basketball team.
In December 2008, Brackett was accepted to Columbia University to be a member of the varsity football team.
Brackett was rated the 77th best quarterback in the 2013 NFL Draft by NFLDraftScout.com.
In August 2013, Brackett was assigned to the Utah Blaze of the Arena Football League. However, in October 2013, the Blaze did not submit paperwork to return to the AFL, making Brackett a free agent again.
On October 28, 2014, Brackett was assigned to the Las Vegas Outlaws. He was named the backup to J. J. Raterink, for the 2015 season. After Raterink went down in Week 9, Brackett was named the starting quarterback for the Outlaws.
On October 16, 2015, Brackett was assigned to the Jacksonville Sharks. He was the backup to Tommy Grady during the 2016 season.
Bracket was selected by the Qingdao Clipper in the 2016 CAFL Draft and was the backup to Bryan Randall during the 2016 season. On October 29, 2016, Brackett relieved Randall and completed 5 of 5 passes for 102 yards and 2 touchdowns as the Clipper lost to the Shenzhen Naja by a score of 47–40.
Brackett was assigned to the Washington Valor on March 1, 2017. Brackett was activated on May 24, 2017 from injured reserve. On May 27, 2017, Brackett made his first start for the Valor and led the team to a 47–48 defeat.
Stats from ArenaFan: