Southend’s midfield changes: Oldaker and Hartigan arrive as Appiah-Forson moves on

It has been quite a few days for Southend’s midfield. Darren Oldaker and Anthony Hartigan are coming in, Keenan Appiah-Forson is on his way out, and Kieron Dyer is beginning to put his own mark on the squad. I like the look of the two arrivals. I am still disappointed to lose Keenan. Both feelings can be true.

After the way last season ended, I wanted to see a plan this summer, not just a collection of names. We have a new head coach, a new approach to building the side and a big challenge ahead of us. The club has now made two signings that say something about the type of team it wants to become. The question, as ever, is whether that turns into better football once the season starts.

On Thursday, 18 June, Southend announced that Oldaker had joined from Swindon Town for an undisclosed fee and Hartigan had arrived after leaving Barnet. Today brought the confirmation that Appiah-Forson will move to Oldham Athletic when his contract expires. He has agreed a two-year deal with the newly promoted League Two club. Three midfield stories in the space of two days, and every one of them matters.

First, the departure that hurts

I will start with Keenan because I think he deserves more than being treated as the outgoing name in a tidy little transfer summary. When he arrived from West Ham in August 2024, Southend were still trying to find some stability and a way of turning promise into results. He became one of those players whose value could be easy to miss if you only looked at goals and assists.

He brought legs to midfield. He wanted to press, recover possession, carry the ball forward and turn a scrappy passage of play into something dangerous. There were times when the game became untidy and his energy was exactly what we needed. No, he was not perfect. There were passes he could have used better and moments when he might have made an earlier decision. But you could see what he was trying to do and how much he put into it.

And he made his mark on our FA Trophy campaign. His goal against Horsham was one of the contributions along the road to that Wembley afternoon when we finally lifted a trophy. I would have liked to see him stay and try to add a promotion to that memory. A player with his willingness to get around the pitch is useful in this division, particularly when opponents do their best to stop you playing.

Southend offered him the chance to remain, but he is taking the opportunity to play in the Football League with Oldham. I cannot blame him for wanting that. We have spent years trying to get back there ourselves, so it would be a bit rich to pretend the attraction is not obvious. Still, there is a sting in seeing a player move to a club that has just achieved the promotion we were chasing.

I wish him every success, honestly. He gave us some good performances, worked hard and was part of a Wembley-winning team. But his departure leaves a job for somebody else: we still need that movement, energy and urgency in the middle, even if the new players give us different qualities on the ball.

Darren Oldaker: somebody who has already done the job

Oldaker is an interesting signing because he already knows what winning this league looks like. He captained Chesterfield during their 2023/24 National League title-winning season. That is not a minor detail. A promotion campaign runs from August through a long winter and into the spring, when nerves can do as much damage as tired legs. He has been part of a side that handled it.

His career has taken him through Gillingham, Dorking Wanderers and Chesterfield before the move to Swindon Town. Last season he made 40 appearances for Swindon in all competitions, so we are not bringing in somebody who has been sitting on the sidelines and hoping for a restart. He has played at League Two level, and he is now stepping back into the National League with a purpose.

There is a clear connection with Dyer, too. They worked together at Chesterfield, where the new Southend boss was on Paul Cook’s coaching staff. That should give both men a useful starting point. Dyer knows what Oldaker can do; Oldaker has some idea of what the manager expects. In a summer with a lot of change, that familiarity could save time.

For me, the important question is how he uses the ball. We can have all the possession figures in the world, but they mean very little if the opposition are happy to stand and watch us pass sideways. I want somebody who can take a pass under pressure, spot the next one and keep us moving. Oldaker’s experience suggests he has the tools to help with that, although he still has to show it in a Southend shirt.

He will also be expected to help the less experienced players around him. Being a captain in a successful side does not automatically make somebody a leader at a new club, but it is an encouraging starting point. We have enough talent in this squad to benefit from a calm voice when the match is getting away from us.

Anthony Hartigan: another promotion winner with something to prove

Hartigan arrives with his own strong record. He was part of Barnet’s 2024/25 National League title-winning team and then played 32 Football League matches for them last season. Before Barnet, he developed at AFC Wimbledon and had spells with Mansfield Town and Newport County. At 26, he is not an old hand coming here for a final payday; he should have plenty of football ahead of him.

What attracts me about this signing is the possibility of a midfielder who is comfortable taking responsibility for possession. Dyer has spoken about wanting to play with intensity while controlling the ball. That only works if the players in the middle are brave enough to ask for it, even when they are being closed down.

Hartigan has been recognised for his performances in the National League and brings experience of being in a team expected to win most weeks. Southend supporters know how difficult that expectation can be. A visiting side can come to Roots Hall, defend deep and celebrate a point as though it were a cup final. We need midfielders who do not get impatient or disappear when the easy pass is blocked.

I am interested to see how Hartigan and Oldaker might work together. Will one sit deeper while the other pushes on? Can they play as a pair without leaving us exposed when the ball is lost? Where does the energy come from if an opponent tries to turn it into a battle? I do not expect all of those answers in June, but they are the sort of things Dyer and his coaching staff will have to settle before the serious football starts.

Two champions, but promotion is not transferable

I can see why Kieron Dyer is pleased. Both new midfielders have National League winners’ medals and recent League Two experience. They know the standards needed to get out of this division, and the manager has spoken about how important they could be in setting the right culture. Those are sensible reasons to sign players.

But a medal does not come with six points in the table. Chesterfield won the division with Oldaker, Barnet won it with Hartigan, and neither of those teams will be playing the matches for us. Southend have to build their own identity. The pair have to settle in with their new teammates, understand the system and deal with the expectation that comes with this club.

I remember how often we talked last season about having good players without always making the most of them. Sometimes we moved the ball too slowly. Sometimes the forwards waited for a pass that never came. At other times we were too open when possession broke down. If these signings give us more control and quicker decisions, that will help. If they simply make us look impressive on paper, we will be back to having the same arguments on the terraces.

It is worth remembering that Josh Popoola has already come in this month as well. There is clearly some serious recruitment taking place, and that is what supporters wanted to see after such an abrupt change in management. I was unhappy about Kevin Maher leaving, and I still am. But that does not mean I should dismiss good business when the club makes it. The fairest way to judge the new set-up will be by what it builds, not by my feelings about how the previous one ended.

What I want to see when the new season begins

My hope is that we become harder to play against without sacrificing the football that makes supporters want to get out of their seats. I want a midfield that wins its share of second balls, knows when to slow the game down and can also spot the moment to get us on the front foot. Most of all, I want players who take responsibility when a match is difficult.

We are going to face opponents who will put ten men behind the ball at Roots Hall. We will face others who press us from the first whistle. There will be small grounds, awkward pitches, injuries, suspensions and all the other things that turn a promising season into a proper test. Promotion winners ought to know what is coming. That is where Oldaker and Hartigan could become more valuable than their transfer announcements suggest.

Then there is the human side. Appiah-Forson was part of a group that brought us a trophy. He has gone, and others may move on as Dyer shapes his own squad. Supporters will naturally have favourites, and some departures will hurt more than others. New signings cannot simply inherit the affection earned by those who came before. They have to make their own connection with the stands, one performance at a time.

Welcome to Southend, Darren and Anthony. Thank you for your efforts, Keenan, and good luck at Oldham. Let us hope this is the beginning of a midfield that can finally help take the Shrimpers back where we belong. Up the Shrimpers.