When Craig Eastmond looks back on winning the 2009 FA Youth Cup with Arsenal, it’s not the final against Liverpool that he remembers most fondly. “I think the highlight of that FA Youth Cup run was at White Hart Lane when we beat Tottenham, when there were about 20,000 fans there,” he says. “That was the best moment for me.”
An Arsenal fan as well as an academy graduate, Eastmond still wears his club loyalties on his sleeve. That quarter-final against Spurs was followed by victory against Manchester City in the semis and a full-on demolition of Liverpool over two legs in the grand finale, completing a league and cup double for the side. Eastmond earned his first professional contract on the back of that success and, in the same age group as future first-team regulars like Jack Wilshere and Francis Coquelin, had to shoulder the expectation that came with it.
“It’s a learning curve, because you’re playing in front of loads of fans and, back in the day, then, [the FA Youth Cup] was huge,” he says. “Now it’s not quite as big because they have the under-23s Premier League and all that stuff… it’s not as big as it was back in the day.”
Unsurprisingly he remembers Wilshere as the beating heart of the team, though he also singles out Jay Emmanuel-Thomas – now a free agent after a short spell in Thailand – as someone who really stood out at the time. “He was so physically strong, he was a handful… [Wilshere] got the move [to the first team] before everyone else, we knew he had something.”
Though he had received a few call-ups to first-team training beforehand – he recalls feeling star-struck the first time he found himself on the pitch with Thierry Henry – he made a definitive step up after that FA Youth Cup triumph. “It’s nerve-wracking because you’re playing against world-class players,” he says, when asked about how he felt when he started to link up with the senior side on a regular basis. “When it comes to playing with them, though, you just get on with it, because they wouldn’t let you go out there unless you’re good enough.”
That was a message hammered home by Pat Rice, who was the one to take Eastmond aside and settle those early nerves. “He was there telling people: ‘Look, I know it’s difficult coming up here but don’t feel out of place. If you weren’t good enough you wouldn’t be here, so just enjoy it, do what you normally do and don’t be shy.’ He told us if we wanted to do a hard pass, to do a hard pass. He wouldn’t get on you, he’d encourage you to keep going.”
Eastmond remembers Arsene Wenger as a more reserved figure, speaking “now and then” but taking a quieter approach on the training ground. He recalls Wenger giving him some familiar advice, however. “[Cesc] Fabregas was the star really, because I was playing in midfield then,” he says. “I started at right-back, then I went to midfield and then the manager was like: ‘I can see you playing in midfield all the time now.’ He told me to watch Fabregas and look at what he was doing, so obviously playing with him that next season was a good learning curve as well.”
Five months after winning the FA Youth Cup, Eastmond was handed his first senior appearance. It was the archetypal Arsenal debut of the late noughties: a team with an average age of around 22 beat Liverpool 2-1 in the Carling Cup, with Eastmond widely praised for a composed performance in midfield. He even played a part in the opening goal, nicking the ball away from Andriy Voronin before Fran Merida fired in an absolute rocket from long range. “You can call it an assist if you want,” he laughs. They all count, in fairness.
Asked what it was like to make his bow for the club he supported, Eastmond says: “I’d always wanted to play for Arsenal and getting a home tie for my first game, obviously it was incredible walking out. The main thing was what Mikael Silvestre said, because he was captain: ‘Look, when you go out there, you won’t hear the fans, you’ll just hear the players on the field. Just enjoy it, take it all in, don’t be star-struck in front of the fans. Don’t complicate it, start with five-yard passes… just do what you can and remember that we’re here to help you if you do muck up.’”
Silvestre doesn’t get much credit for his time at Arsenal, but Eastmond still appreciates those quiet words of encouragement in the tunnel. He would go on to make 10 appearances over the next 12 months and, on the surface, everything seemed to be going well. Slowly, though, he started to feel that he was missing something. “It’s always hard to break in when you’ve got world class players, international players and all that in the team. It was like: ‘Do I stay here, and keep trying, keep trying, keep trying?’
“When you’re young, you’ve still got time on your hands and it’s alright playing reserve [football], but you want to be doing what they’re doing. After a while it kicks in that you want to just play week in, week out.”
A year after his debut it dawned on him that, if he wanted consistent game time, he might have to leave the club. “I was getting a taste of the training, but obviously I wasn’t playing,” he says. The long journeys for Champions League games started to sap his morale when they ended in 90 minutes on the bench and, when he finally got a start against Shakhtar Donetsk, he scored an unfortunate own goal and was brought off early in the second half. “I was travelling abroad with them and all that. Basically you just want to be a part of the team, not train with them for a bit and then not play.”
Eastmond got the chance to go on loan to Millwall later in the season, but it was there that his luck started to turn. He suffered a broken fibia and, as he was returning to full fitness, he found that he had been crowded out of the Arsenal squad by the new academy intake. “The whole process where I was out took four months and that’s where I was unlucky with injuries,” he says. “I was nearly back fit, but by then they were playing other youngsters. If I was fit and didn’t get injured, I could have been playing. It was frustrating, but it’s part and parcel of football really.”
Despite a loan at Colchester United which was hampered by a fractured metatarsal, Eastmond was offered a permanent move and decided to take it, joining former teammate and fellow FA Youth Cup winner Sanchez Watt at the club. He established himself in Essex but, after a change of management and several more injuries, he found his minutes dwindling. After a spell at Yeovil Town where he made just one appearance, he found himself without a club in the summer of 2015. “Obviously when you’re not playing for a while, you’re back in pre-season and you ain’t got a club, it’s difficult,” he says. “All your friends are back in training and you’re just at home, in the gym or whatever.”
That was when he got the call from Sutton United, then in the National League South. “I was like: ‘Yeah, that’ll be a good stepping stone and I can keep working on it and hopefully get a move,’” he admits. “But since then, it’s worked out well. Sutton have looked after me, I’ve been playing week in, week out and just enjoying my football again.”
Eastmond has now been at Sutton for five years, making over 150 appearances for the club and winning promotion to the National League along the way. Why has he settled down at Gander Green Lane, in Sutton’s sleepy corner of south London? “It’s a good club, it’s local for me. Obviously I’d still like to play higher, if I can. But here I get game time and, if you go to another club, you can play one week and end up out for a while… I’m at that age where it’s all about playing games.”
While it may seem a world apart from Arsenal, Eastmond has made a name for himself in non-league. It’s been a memorable few years for Sutton, with the club recording their best ever league finish three seasons ago and, in 2017, hosting Arsenal in the fifth round of the FA Cup. Eastmond played the full 90 minutes and helped to frustrate his former employers for much of the game, though the visitors eventually ran out 2-0 winners.
“Obviously we knew it would be hard to win, but we gave it all we got,” he says. “That’s all you can do really against a team like Arsenal.”