The American took charge at Liverpool in October 2010 after buying out countrymen Tom Hicks and George Gillett - who had become unpopular with the Anfield faithful.
A change of ownership also brought on a new philosophy, especially regarding transfers with a committee in place to decide which players will be brought to Merseyside.
That finally appears to have borne fruit under Brendan Rodgers this season, with the team sat top of the league with four weeks to go and in sight of a first title in 24 years.
Despite investing an estimated £515million to gain control at the club as well as attract stars such as Daniel Sturridge and Luis Suarez, Henry claims a top-four finish was the limit of his ambitions before the season started.
"We had our sights set on a top-four finish because we're building," American Henry told BBC Sport.
"It's a challenge with the way the league is structured, so if we were fortunate enough to win this year, I would say we're ahead of schedule."
Henry has a history of bringing glory back to faded teams, having taken over the Boston Red Sox in 2002, who had gone 84 years without winning MLB's World Series.
After breaking that duck in 2004, the Red Sox also won titles in 2007 and 2013, with Henry acknowledging similarities between his baseball team and Liverpool.
"We've been a part of something really incredibly special here (Boston) - we're beginning to feel we're a part of something really special there," he added.
"The history (at Boston) is irreplaceable. It's the same at Anfield.
"You've had European nights there and historic days that could never be replicated. People come from all over the world.
"When (Liverpool chairman) Tom Werner and I were in Warsaw at a European Club Association meeting we were told by a number of executives from other clubs that the best experience they've ever had was at Anfield.
"So, we're committed to doing whatever it takes to get Anfield to where it needs to be over the next 20, 30, 40, 50 years and its challenging but it's also rewarding and we'll get it done."
