Once upon a time, when Gareth Bale was still plying his trade at left back and Aaron Ramsey was yet to burst onto the scene, Wales’ most exciting young attacking prospect was a striker named Freddy Eastwood.

In August 2007, the 23-year-old had just scored on his international debut in a 1-0 friendly win against Bulgaria.

The strike was impressive enough; Eastwood latched onto a long ball fourty yards from goal, cut inside near the edge of the box and drilled a powerful yet placed shot past the sprawling Dimitar Ivankov.

“It was a really special goal,” reviewed manager John Toshack. “Now we have got a player up front who knows his business. We have been aware of his goalscoring exploits and have worked hard to make sure he became a Wales international.”

Seven years (and just ten more caps) later, Eastwood retired at the age of 30 after being released by Southend United, the club where he had effortlessly and impressively crafted legend status.

On the surface this might resemble a tale of wasted potential, but it is one that features enough highlights to ensure that he remains fondly remembered in many circles.

Born in Epsom, Surrey, Eastwood moved to Essex to forge a youth career at Southend, although he rejected a scholarship there to join a West Ham youth team that boasted Jermain Defoe, Anton Ferdinand and Glen Johnson amongst its ranks.

He first strayed into the radar at Grays Athletic, scoring 37 goals in all competitions in 2003/04 and emerging as one of the standout performers in the Isthmian League.

His exploits caught attention rising through the leagues, starting with a rumoured £100,000 bid from Third Division Northampton Town, escalating with interest from Second Division Swindon Town and culminating with a trial at Premier League Charlton Athletic.

Ultimately Eastwood stayed at Grays, maintaining form with a further seven goals in the opening two months of the following season.

Southend manager Steve Tilson could offer two things Eastwood’s previous suitors couldn’t; proximity and the chance to resolve unfinished business.

He initially signed Eastwood on loan to strengthen an injury-riddled strike force and installed him straight into a team that had battled against relegation to the Conference during the previous two seasons.

It paid instant dividends; Eastwood scored a hat-trick in a 4-2 win against Swansea, the first of which was a header that nestled the back of the net after eight seconds and set an English league record for the quickest ever debut goal.

When further league goals against Scunthorpe and Oxford and a double in the Football League Trophy versus Shrewsbury quickly followed, Tilson had no choice but to make Eastwood’s move permanent the following month.

The 21-year-old was rapidly established as the focal point of a team that improved upon their prior campaign by thirteen places to surprisingly nab a play-off spot in fourth. He scored 20 goals in the league but saved his best for last.

After netting the lone goal in the Shrimpers’ 1-0 semi-final aggregate win against former flame Northampton, he opened the scoring in the 2-0 final victory contested against Lincoln.

If Southend’s promotion from League Two was a pleasant surprise, the following season their fans were in dreamland. Eight successive wins between August and October set the tone for the campaign and established them at the peak of League One, a position they rarely surrendered all season.

The rise to a new level didn’t faze Eastwood either and he improved his league tally with 23 goals that saw him finish as joint top scorer in the division and included Southend’s 5,000th league goal, a late winner against Blackpool. His total return of 25 in all competitions is yet to be matched by a Southend player since.

With so much attention geared towards Eastwood on the pitch, eventually some seeped away from it. The fans and media alike become intrigued with Eastwood’s life as a traveller; he was a proud member of a Romany ‘gypsy’ community that resided on Cranfield Park Avenue, a site near a dual carriageway in Basildon.

Supporters began to excitedly share stories of Eastwood exercising his horse on the A127 on the morning of matchdays and his dispute with Basildon Council when they questioned the legality of his property dominated local headlines. “The wheels on his house go round and round!” became a popular chant on the Roots Hall terraces.

A side effect of Eastwood’s heritage and strong family ties were that it increased Southend’s chances of keeping him. Despite increasingly intense transfer speculation, Eastwood stayed at the club for their adventures in the Championship.

Unsurprisingly for a team that had just enjoyed back-to-back promotions, Southend found themselves punching considerably above their weight. By the start of November they had recorded just two wins in the league and whilst Eastwood was not struggling for goals, he wasn’t maintaining his habitual one-in-two ratio either.

However, that month brought Eastwood’s most famous moment. The fourth-round draw of the League Cup secured Southend a glamour tie at Roots Hall against Manchester United, who lined up with the likes of Cristiano Ronaldo, Wayne Rooney and Darren Fletcher and anticipated minimal difficulty in progressing to the quarter-finals.

After an opening twenty-six minutes largely dominated by United, David Jones fouled Jamal Campbell-Ryce 30 yards from goal and Eastwood stepped up to take the resulting free kick against the team he supported as a boy.

After the ball left his boot, it smoothly glided over the wall and into the top right corner of Thomas Kuszczak’s goal and as Eastwood slid on his knees towards the television cameras, the cries of “Doo doo doo doo, Freddy Eastwood!” could probably be heard in Land’s End.

Southend held on for a famous victory but were cruelly denied League Cup glory by an extra-time exit against Tottenham in the next round and by the end of the season their inevitable relegation from the Championship had been confirmed.

The task of keeping hold of Eastwood, who finished the campaign with a respectable sixteen goals in all competitions, seemed nigh on impossible. The Seasiders fans’ worst fears were confirmed when Eastwood joined Wolves for £1.5 million in July 2007 and bid farewell to a club at which he had heavily contributed to arguably the greatest period in their history.

The early indications at Molineux suggested that Eastwood was ready to take yet another step up. He netted four goals in his opening three games and was declared Championship Player of the Month for August.

It was at this time he scored on his debut for Wales, having been finally able to earn his first cap after his previous call-up in May was curtailed by a back injury.

Despite his ‘Basildon boy’ reputation, Eastwood qualified to play for Wales through his grandmother and quickly established himself as both a fan favourite and John Toshack’s new protégé.

He earned plaudits for his shift in Wales’ next match (a 2-0 defeat against Germany) and netted their first goal in a 5-2 Euros qualifying win against Slovakia four days later.

Little did anyone know that would be the penultimate time Eastwood would score that season. He drifted in and out of the Wolves team, becoming a fierce source of debate amongst factions of fans who felt that he deserved more consistent starts and was overrated respectively.

Several reasons were offered to explain his downturn in form; homesickness, an inability to adapt to new tactics and the pressure of competing with the likes of Jay Bothroyd and Sylvan Ebanks-Blake for a starting spot.

He was more adept at keeping his place in the Wales starting eleven but initial fan excitement slowly turned towards frustration when he drew blanks against the likes of Norway, Ireland and Cyprus and only built upon his tally with a double against Luxembourg.

In total the 2007/08 season brought just ten starts in the league and by the time Eastwood had started to creep into ‘worst signing of the season’ compilations, both player and club agreed that a swift decoupling was the best course of action.

“It’s nothing personal, but it hasn’t worked out how either of us would have liked. He hasn’t fitted into my team but he wants to play and will do well elsewhere.” suggested manager Mick McCarthy.

Eastwood joined Coventry for £1.2million to begin a relatively uninspiring four years at the club. There were sporadic flashes of brilliance, most notably a league hat-trick against Peterborough, but he became a forgotten man in the realms of the Championship who appeared increasingly grateful just to get a game.

Appearances on the international front dried up too when Toshack’s replacement Gary Speed refused to exhibit the same level of patience. Eastwood’s final appearance for Wales came in 2011 with a twenty-three minute cameo in a 3-0 defeat against Ireland.

Towards the business end of the 2011/12 season he was struggling to even make the bench in a team that was rapidly deteriorating towards relegation. When Coventry said he was free to leave on loan that March there was only one place he turned to, although Eastwood’s reunion with Southend was built on more than just nostalgia.

As far as he was concerned, they were the catalyst to revitalise his career whilst Southend, by that time traversing near the top of League Two, felt he could lead the final push to secure a play-off spot.

A rusty Eastwood only managed two goals in nine appearances but the team finished 4th. Despite their promotion hopes being dashed in the play-off semi-finals, Southend offered him a two-year contract when he was released by Coventry and he returned to the club where he was universally adored in a full-time capacity.

Struggling for form after knee surgery in the summer, Eastwood found the net just four times in thirty-one appearances during his first full season back, although the supporters’ enthusiasm was unwavering and his goals appeared to be celebrated louder than anyone else’s.

The next campaign promised greater things when he began the season in typically blistering form with four goals in August, although as the games went by and his knee injury returned he increasingly found himself a castaway in the young squad Phil Brown was building for promotion.

Southend found themselves in an impossible situation and a deliberation on whether to lead with their head or heart; in the end they opted for the former and Eastwood was released at the end of the season.

Fans were divided over the move with some arguing that Eastwood needed to make way for younger prodigies and others adamant that he was unfairly cast side, but all agreed that the club’s then fifth all-time top goalscorer was a lovable legend.

Frustrated by his injuries and perhaps feeling that he had achieved all he could, Eastwood never joined another club and quietly retired. Despite enduring a career which featured an early peak followed by disappointing lows, his talents brought joy to thousands of football fans and featured moments which are still recounted to this day.

A passing mention of his name will likely prompt a smile from any Southend fan who firmly remembers his talismanic role in a team that achieved remarkable back-to-back promotions and claimed a cup scalp or two along the way.

Today Eastwood can often be seen cheering on Freddy Eastwood Jr, his son who turns out for the Southend Under 18s. Time will tell if one day there will be a second Freddy Eastwood Southend supporters rave about.


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Sam Pearce