Chelsea, for the most part, have always been happy-go-lucky in the transfer market. Before the careless spending of the current Todd Boehly regime, former Russian owner Roman Abramovich regularly burnt holes in his pockets to fuel the Blues’ dominance throughout the 2000s and early 2010s.

While the current spending often feels like their American owner is simply throwing money at the problem, Abramovich’s extravagance was more calculated – spending big to cash in even bigger from a commercial standpoint. But that’s not to say the old ownership didn’t have its fair share of costly flops, too. One of the West London club’s biggest downfalls was not having enough faith in their own academy.

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Belgian aces Kevin De Bruyne and Romelu Lukaku are prime examples of talent Chelsea tried to steal from other clubs. But back in 2006, another young duo arrived, only to vanish just as quickly. Sixteen-year-olds Tom Taiwo and Michael Woods were snapped up from Leeds United in a bid to poach rival clubs’ unpolished gems.

But the plan spectacularly backfired when an out-of-court settlement forced the Blues to fork out a whopping £5 million for their signatures – an exorbitant price at the time that left Chelsea feeling the pinch. And now, their names are anything but familiar.

Leeds’ Fury At Chelsea After The Blues Stole Their Talent In 2006

Both players felt they made the move with their best interests at heart

Under Abramovich, Chelsea exploited something of a loophole in youth recruitment – rather than developing their own academy talent, they spent small fortunes poaching young prospects from other clubs, or sometimes, they wouldn’t even offer any compensation at all. As mentioned earlier, this approach didn’t sit well with Ken Bates, who had sold Chelsea and taken up the chairman role at Leeds United a year prior.

Bates saw the tactic as a misuse of power – one that dangled big promises in front of teenagers, only to discard them if they failed to meet expectations. The dispute became personal, The Athletic reflected in 2020. He held a press conference at Elland Road, urging the Premier League and FA to investigate alleged tapping-up by Chelsea.

The west London club took particular offence to him labelling their board “a bunch of Siberian shysters,” accusing him of racism – a charge Bates dismissed, saying: “Racism is the last card of a desperate man.”

After months of wrangling, Chelsea agreed in October 2006 to pay £5 million in compensation and review their recruitment policies. Bates withdrew his complaints, but his prediction – that the young duo wouldn’t handle the pressure of the West End and be better of honing their skills in Yorkshire for longer – proved all too accurate.

Michael Woods

Whitby Town

You’d be forgiven for mixing them up, as neither made a Premier League appearance for the West London side before moving on. Michael Woods, a central midfielder, did make two FA Cup appearances under Jose Mourinho, but his progress at Stamford Bridge was hampered by a series of injuries.

He had a short and unsuccessful loan spell at Notts County and was released by Chelsea when his contract expired in 2011. After seven months without a club, Woods signed short-term deals with Yeovil Town and Doncaster Rovers but failed to make a lasting impression. He then dropped out of the Football League, joining Harrogate Town in 2013 — a move that proved to be exactly what his career needed.

Woods scored nine times in 35 appearances for Harrogate, earning a return to the Football League with Hartlepool United in 2014, before a return to Harrogate in 2018 was followed by stints at the likes of York City, Dover Athletic, and Blyth Spartans.

Now, at 35 years old, he’s playing out his final years in the lower tiers of English football again, most recently signing for Northern Premier League Premier Division side Whitby Town in February. It’s a far cry from the glitz and glamour of the West End, but no doubt a picturesque spot to see out his playing days in the much-loved seaside town.

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Tom Taiwo

Retired

Highly-rated youngster Tom Taiwo suffered a terrible stroke of luck soon after signing for Chelsea that went far beyond the fault of his new club, breaking his leg two days before he was due to make his youth team debut. He recovered but was never given a chance in the first-team during his four-year stay in west London.

The midfielder struggled on loan at Port Vale but did impress at Carlisle United in the 2009/10 season and the Cumbrians rewarded him with a permanent contract. Taiwo then moved to Scottish club Hibernian in 2012, where he stayed for just two years before stints with Falkirk – where he featured over 100 times – and Hibernian Academical.

Taiwo was named as a substitute in all of England’s games at the 2007 European Under-17 Football Championship, though he didn’t feature in the final defeat to Spain. He did come off the bench in the 1-1 draw with Belgium and the 1-0 semi-final win over France.

Unfortunately, his time at Hamilton didn’t go as hoped. Manager Martin Canning judged him to be a poor signing, and Taiwo left the club by mutual consent in May 2019 after making 19 appearances in the 2018-19 season. He retired due to injury in June 2019 at just 29, but not before earning a reputation earlier in his career as a tough-tackling, wholehearted player.

He then went on to be an academy coach at several places where he helped other kids to make much wiser decisions than he did when he was younger, though his whereabouts now aren’t completely known.

All statistics courtesy of Transfermarkt (correct as of 03/06/2025)