Football League World
·22 mars 2025
Bolton Wanderers beat Burnley and West Brom to £10k transfer gamble - it flopped but still landed them a 10x profit

Football League World
·22 mars 2025
Bolton's gamble to sign Kaiyne Woolery proved to be a flop
Owing to the success of Jamie Vardy with Fleetwood Town and Leicester City, virtually every EFL club was scouring the non-league scene in the mid-2010s looking for the next big prospect working their way up the footballing ladder.
Bolton Wanderers thought they'd identified the next hidden gem in Tamworth's Kaiyne Woolery, but the curious case of his Bolton career proved his move was highly misjudged, although there was a huge silver lining to his failed transfer.
At the time, Bolton were stagnating in the Championship, struggling to get back into the Premier League, which was ultimately where they longed to be, and they took the unusual approach to try and bolster that quest by dipping into non-league rather than signing proven players.
That perhaps owed to the financial issues the club faced at the time, and although it could be deemed admirable that Wanderers were open to giving non-league players a chance, they learned the hard way with this deal that not every non-league striker will turn out like Vardy.
In August 2014, Bolton swooped to sign Woolery from non-league Tamworth for a fee of £10,000, and no, that's not a typo, the fee was believed to be £10,000.
He was a real coup at the time, as Bolton beat off competition from then-Premier League Burnley and West Brom.
Some people reading will probably think they could've bought Woolery themselves, but that is genuinely understood to be the fee Bolton paid to bring him to the EFL for the first time in his career and had him the break he'd longed for all these years.
Coming in with a fearsome reputation in non-league as a bit of a speedster and able to play up front or off the wing, there were certainly striking similarities to Vardy, but the footballing abilities ended up being incomparable.
Woolery only played 24 times for the Trotters in all competitions and scored a paltry three goals, giving him a strike rate of a goal every eight games, which falls well below what you'd expect of a striker at second-tier level.
That adaptation process from non-league football into league football proved to be a massive obstacle to overcome for Woolery, who soon found himself out of favour at Bolton, even after their relegation into League One.
Wigan Athletic boss Gary Caldwell obviously saw enough in Woolery to take a calculated gamble on him in August 2016, spending a rumoured £100,000 on him to bring him to Wigan from their bitter rivals.
That handed Bolton a handsome 10x profit on a man they'd invested £10,000 in two years prior, and although his on-field contributions certainly weren't up to standard, the deal was certainly a success from a financial standpoint.
Woolery's time at Wigan was a disaster too, making just a sole appearance for the first team, but like Bolton, the Latics turned a handsome profit on Woolery too, selling him to Swindon for a fee of £350,000.
The best football of Woolery's league career came at Swindon, where he contributed to 28 goals in 110 appearances,
He currently turns out for Cypriot side Anorthosis and has gone on to have a respectable career after Bolton took a huge gamble on him back in 2014.
Although he didn't deliver on the pitch, a 10x profit on a transfer certainly isn't to be sniffed at.