Often regarded as one of the most gifted academy graduates to emerge into the first team frame, Henry has found first team opportunities hard to come by.
Having been at the club from an early age, coaches and supporters held high hopes for the Woodley born winger as one player who would be a star player for the club for years to come. Henry even had the luxury of turning down Chelsea in the summer of 2005.
But luck wasn’t on his side when in his teens; he tore cruciate knee ligaments which kept him out injured for the whole of the 2005-2006 season.
This probably held back his development and as the club enjoyed success, winning the Championship and enjoying a respectable two year spell in the Premiership, Henry went out on-loan to Nottingham Forest and Norwich City.
But it was at Bournemouth where he initially made a name for himself, scoring four goals in 11 appearances in 2007.
In the same season, he finally made his Reading debut in the 3rd Round Carling Cup tie with Liverpool when he came on as a 2nd half substitute, an appearance long overdue.
The following season, as Reading returned to the Championship, Henry saw more first team opportunities arise and played an influential role in one of the team’s results of the season, winning 3-1 at Birmingham in December 2008.
Later that season, he began the first of two loan spells at Millwall and caught the attention of Kenny Jackett, starring in 18 games and scoring three goals in the process.
When his mentor and former youth team coach Brendan Rodgers was appointed as Reading manager the following summer, many felt Henry would get the opportunity he craved into first team action with the Royals.
However that never quite emerged and again Millwall came calling for his services where he scored five goals in nine games.
But with competition fierce with Jimmy Kebe playing the best football of his Reading career, and Michail Antonio coming back from a loan spell at Southampton, opportunities in the first team will have been hard to come by for Henry, who will depart with the best wishes of all supporters.
Henry will do well to take inspiration from former Reading players Simon Cox & Nathan Tyson who both left the club for the sake of their own career’s, but made great progress when playing regular first team football and in the case of Cox, is now a Premiership striker.
Disclaimer: The views in this article are that of the writer and may not replicate those of the Professional Footballers' Association.