Jordan Maguire-Drew’s two-year spell at Leyton Orient feels littered with ‘what if’ moments as the 23-year-old showed flashes of brilliance before departing E10 this summer with a sense of unfulfillment.
“I can’t speak highly enough of my time at Orient, but I was a bit disappointed with how it ended,” Maguire-Drew told The LO Down Podcast.
“I thought I’d be there for ‘x’ amount of years but obviously things happen and you have to move on. That’s life.”
The winger joined the club in the midst of a title challenge and from the outside it seemed like the type of ambitious signing that proved Orient were already planning for life back in the Football League.
Things went as well as could be expected in those first few months, the O’s ending up lifting the National League title in April and a couple of weeks later graced Wembley for the FA Trophy final.
However, what seemed like a dream season soon turned to tragedy as Orient’s talismanic manager Justin Edinburgh passed away shortly after guiding the club back to the Football League.
Like so many connected with the club at that time, the news hit Maguire-Drew hard.
“When it happened, I was on holiday. I thought to myself this can’t be happening, I thought I was dreaming. I still struggle to get my head around it now.”
Despite only working together for five months, the impact Edinburgh had on Maguire-Drew is evident.
“His man-management skills were the best I’ve ever had by a country mile. He knew when to put an arm around you and he knew when to kick you up the backside.
“He made you feel ten foot tall, and you just felt so confident going out onto the pitch. That title run-in was so enjoyable because he took a lot of the pressure off us. I can’t speak highly enough of him.”
Following their title success, the club should have returned for pre-season that summer on a high. But instead, they were in mourning.
Coming back to the training ground without their leader was tough.
“It just didn’t feel right. We missed his presence. He was always very loud, very outgoing and loved the banter,” Maguire-Drew said.
“You would hear him from a mile away before you even saw him. So then when we came back and couldn’t hear his voice, it took so long to get used to it.
“I just felt like he was going to come walking through the door again and everything would go back to normal. It was such a weird time, and it was a tough transition not just for myself but for everyone.”
As was to be expected given the circumstances, the O’s started the season indifferently as interim boss Ross Embleton quickly stepped down to be replaced by former West Ham midfielder Carl Fletcher.
Fletcher’s time in charge proved to be a disaster which lasted just 29 days with Maguire-Drew feeling any new arrival into a club still grieving was always going to be too much to deal with.
“It’s tough for a manager to come in and try and change things so suddenly without a pre-season and any real time with the players.
“I understand you want to come in and put your own footprint on the club and how you want everyone to play.
“But I think you’ve got to do that over a gradual period because if you do too much too soon players get confused and then you get frustrated because they’re not playing how you want them to play. It’s like a domino effect.”
Embleton took up the role once again after Fletcher’s dismissal, eventually being appointed on a permanent basis in January 2020.
Over the course of the following year, Maguire-Drew didn’t receive the regular playing time he believed he deserved under Embleton, leaving him at a crossroads going into the festive season.
“I felt the hard work I was putting in wasn’t reciprocated in the performances and platform I was giving.
“Over Christmas I took some time to reflect, especially because of Covid and the uncertainty of football.
“I felt I needed to go out on loan to go and play some games because I didn’t feel I was going to get those opportunities at Orient with Ross (Embleton) still being in charge.”
Reflecting on his relationship with Embleton, Orient’s former number ten was open and honest in his assessment.
“We did get on but when he’s the manager he’s got to make tough decisions and obviously I wasn’t going to agree with him if I wasn’t playing.
“I said to him “you’re killing me because I need to play regular football.” Whenever I was called upon, I felt I did well but it felt like I had to go and score a hat-trick every week to stay in the team.”
Maguire-Drew’s time at Orient could also have undoubtedly gone differently as shortly after he left the club to join Crawley Town on-loan in January, Embleton was replaced by club captain Jobi McAnuff.
“I would have loved to have played under Jobi (McAnuff) because he was a good coach, and I can’t speak highly enough of him.
“If I’d have stayed and been under Jobi, it might have been a different story, but that’s hindsight and I don’t regret the decisions I’ve made.”
After the loan spell at his hometown club, the 23-year-old was subsequently released by the O’s.
Maguire-Drew has now found a new home at National League side Woking where he’ll be hoping to receive the regular playing time he so clearly desires and plot a way back to the Football League.
You can listen to the full version of this interview on The LO Down Podcast.