The American went to Spurs instead, after Henderson scuppered the deal by insisting he did not want to leave Anfield.
He is determined not to give up on his Liverpool dream, and after just one season you can understand that as a young player, but what damage will have been done to his confidence by the club's lack of support?
The failed negotiations are now in the public domain, and Henderson has to try to rebuild his Liverpool career knowing that the club saw him as expendable.
Kenny Dalglish was the manager who brought him in, and many feel the boss was too staunch in the defence of his signings, but for players like Henderson, seeing their manager repeatedly go into bat for them in pre-match and post-match press interviews must have been a relief, contrasted with the Paolo di Canio example of labelling his young Swindon goalkeeper as 'one of the worst players I have ever seen at a football match.'
Under Dalglish it didn't work out, and Brendan Rodgers clearly has his own ideas. The signing of Joe Allen was a sign that he wasn't ready to place his trust in Henderson just yet.
At present he is behind Jonjo Shelvey in the pecking order too, and has not yet featured for a single minute of the Premier League season so far, watching on from the bench.
Of all of Kenny Dalglish's big money signings, Henderson is perhaps the one with the most potential to come good. Carroll has been dispatched to West Ham, not part of the manager's plans, Downing remains as frustrating as ever, and at 28 is unlikely to substantially improve.
Charlie Adam has been sold on, while Henderson at just 22 still has a good chance of improving and fulfilling his potential.
He still has a lot to work on in his game, namely carving a niche for himself. It is often asked what is his strongest attribute, what does he bring to Liverpool's midfield, and that is what he has to work on. He is a good passer of the ball, and he has the potential to fulfill a role similar to Michael Carrick at Manchester United,
He has been dropped from the England squad for the upcoming qualifiers, with the United man taking his place, and if he is not featuring for Liverpool he faces an uphill task to get back in, but with the Europa League games set to bring around a degree of squad rotation, he will get his chances.
Has Brendan Rodgers and co knocked his confidence by trying to offload him this summer? For sure, but it will be up to Jordan to respond on the pitch. If it doesn't go well then he may start looking for an exit in January or next summer.
There is no question Liverpool have treated him badly, and there was no real reason to do so, with the Dempsey pursuit futile. It is just another piece of damage to repair from the club's disastrous end to the summer transfer window.
Do you agree the club treated Henderson badly? Does he still have a future at Liverpool?
image: © kong niffe