At the age of 31, and with two years left to run on his contract, a decision needs to be made on what happens next for the captain who lifted the Champions League and Premier League trophies for the club and secured himself a place in Liverpool folklore.
Now the time has come for Henderson to get the contract he deserves. After Gini Wijnaldum was allowed to leave Anfield on a free transfer last month, losing the skipper ahead of the new season would be very embarrassing for the club.
I have to admit Henderson has proved me wrong over his 10 years at Liverpool – and I am not alone in that.
When Kenny Dalglish bought him during his second spell as manager, back in 2011, I was not convinced he had what it would take to become a Liverpool player.
At the start, he was playing on the right side of the midfield and didn’t seem to have what you need to play for a club where expectations will always be so high.
Then, year by year, we have seen him blossoming, and he learned so much from Steven Gerrard before he took over from him as Liverpool captain.
Then, in 2019, Henderson’s role in the Champions League triumph ensured he will forever be remembered as a great Liverpool captain.
To add the Premier League title to his record a year later cemented that legacy – and he has put himself in the discussion when it comes to who is the best Liverpool captain.
Henderson has fought harder than most to prove himself, and from the time I have spent with him, the success that has come his way couldn’t have happened to a nicer fella.
Jordan is a really decent lad, and everyone who works with him says what a fine professional he is.
You need people like Henderson around a football club, but looking from the outside you would surmise that agents are doing some work behind the scenes.
There are rumours that Arsenal are interested in him and that wouldn’t be a surprise, because he is a superb leader and player.
With those stories out there, Jordan and his agent can use that as a tool in their negotiations with Liverpool to get the contract he deserves.
I know he has had a few injuries over the last couple of years, but the fans will not be happy if they see Wijnaldum and Henderson leaving, one after the other.
That would give the impression that something is not quite right behind the scenes at Liverpool – and the club can’t allow that perception to arise.
Henderson and Wijnaldum are two players who were vital to the success of the team under Jurgen Klopp in recent years – and even though they have hit that 30 mark, there is no reason to think they are past their best.
You look at someone like James Milner – at the age of 36, he epitomises what a player can contribute to a team in the latter stages of his career.
He is like a spring chicken and in pre-season he is as fit as anyone in the squad. That shows this idea that players hitting the age of 30 are on the way down is miles off the mark.
The way players look after themselves now is very different to my days as a player, with sports science and improved diets ensuring a career can last well into your 30s.
So, this is a moment for the agent, Jordan, Liverpool’s money men and Klopp to sit down and get this resolved.
I’m sure Jordan wants to stay at Liverpool, given everything he has achieved at the club. And if that is the case, there has to be a way to find an agreement for him to stay.
Liverpool is one of the biggest clubs in the world, and there is no way wages should be an issue when it comes to getting him tied down to a new contract.
What is an issue is the unwillingness of the club to give long contracts to players over 30.
All in all, the club need to nip this story in the bud quickly and make sure the captain is not tempted by bigger money elsewhere.
Henderson is not the only one in this squad in the 30-plus age bracket with contract discussions coming up because keeper Alisson Becker, Fabinho, Sadio Mane, Mohamed Salah and Roberto Firmino are all in that category, so there are some big calls to make in the next few years.
You can’t let players run contacts into the final year as they will then almost certainly leave on free transfers and get a load of money from the next club they show up at.
That’s what happened with Wijnaldum and we could be in a position where Liverpool players look at the money Gini is getting in Paris and think they fancy some of that action.
Liverpool is a massive business and if the owners want the club to stay at that level, they have to invest in the squad to ensure Klopp is given the best chance possible to gain success.
I thought they could and should have spent a little more last summer, even if the pandemic affected the budgets.
Chelsea are now trying to sign Erling Haaland and Robert Lewandowski, Man United have netted Jadon Sancho and are closing in on Raphael Varane, and Man City will also spend big again.
So Liverpool can’t put themselves in a position where they are left behind because their Premier League rivals won’t stand still.
What Klopp achieved with Liverpool without spending big money, when you look at incomings and outgoings, has been amazing.
So, hopefully, the club now backs him, by ensuring his top players stay and that they add to what they have.
This is a huge business, and to ensure the value of their investment remains at its peak, Liverpool’s owners need success on the field to generate more revenue.
That means keeping proven performers and then adding a few extra ingredients to spice up a team that lost its way a little last season.
With fans returning to Anfield, one factor that was sadly missing in Liverpool’s armoury will be back.
Now Klopp needs the club to give him the support to keep his key players and reach for the stars once again.