Wright re-joined the club in August 2015, initially on a short-term deal, following his release from Leyton Orient.
The defensive-minded midfielder previously had a successful stint with the Gills on-loan from Charlton Athletic during the 2008/09 season; it was from his corner that Simeon Jackson scored the winning goal in the League Two play-off final victory over Shrewsbury Town at Wembley.
He signed his first professional contract at The Valley in 2007, aged 17, and spent virtually the entire 2007/08 season on-loan at Barnet. Wright scored his first professional goal in the London club's 4-2 defeat to Stockport County in October 2007, and made 34 starts for the Bees.
Prior to his first spell at the MEMS Priestfield Stadium, he also went on-loan to Brentford, but was unable to become a first-team regular at his parent club. A two-year spell between 2009 and 2011 at Scunthorpe United followed his release from the south east London side; memorably, his first goal for the Iron came in September 2010's League Cup game against Manchester United at Glanford Park.
He joined Millwall in November 2011 on a free transfer, but spent the latter part of his three-and-a-quarter years at The Den on loan to Orient (November to December 2013, then October to January 2015) and Crawley Town (September to October 2014). He subsequently joined the Os in January 2015 immediately upon a contract cancellation at Millwall, but his arrival was not enough to prevent them from being relegated to League Two five months later.
Wright's first goal for the Gills came in March 2016's 3-0 victory over Crewe Alexandra; prior to that, his last was for Orient against the Gills in an entertaining 3-3 draw at Brisbane Road on Easter Monday the previous year. He captained the side on a handful of occasions in the 2015/16 season, and also finished runner-up to Bradley Dack
in the Player of the Year vote.