Premier League Transfers: 10 Worst Deadline Deals That Could Happen and Why

With the world football transfer window nearing closure, clubs will be involved in last-minute deals that with hindsight may prove to be nothing short of unacceptable or absolutely brilliant.

The good will always exist with the bad and without further ado, here are the 10 worst deadline deals that could happen and why they would be the worst.

Raul Meireles

Transfer Type: Transfer

Proposed Destination: Chelsea

Worse For: Liverpool

Reason: Sending Raul Meireles is not the kind of move Liverpool FC will want to make.

Not only would it strengthen Andre Villas Boas' hand at Chelsea, i.e. bringing in Portuguese talent a la Jose Mourinho, it would strengthen Chelsea's midfield even more.

If Liverpool are true league title contenders, then they'd know that rivals refrain from allowing moves like that. Besides, £8 million plus Yossi Benayoun is money they don't really need, to be honest.

Andre Santos

Transfer Type: Transfer

Proposed Destination: Arsenal

Reason: There is no doubting Arsene Wenger's love for obscure players, but is Bolton Wanderers' Gary Cahill bad enough that Wenger must reach so far as Fenerbahce in Turkey for an alternative, of who very little —at best— is known of? 

Okay, he's Brazilian. What else?

Or, Wenger could just get someone with a known and proven track record of winning?

Romelu Lukaku

Transfer Type: Loan

Proposed Destination: Stoke City

Worse For: Chelsea

Reason: With Didier Drogba injured and Salomon Kalou and Nicholas Anelka already practicing their anonymity roles just in case of a rainy day, Chelsea cannot afford to let Romelu Lukaku go.

More importantly though, and with all due respect, Stoke City is not the place to go to polish a gem like Lukaku. If you want to produce a mid-table striker like Kenwyne Jones, okay. If you want a world beater, keep him at Chelsea.  

Park Chu-Young

Transfer Type: Transfer

Proposed Destination: Arsenal

Reason: I can quite tell head from tail in this one.

Arsene Wenger rarely plays 4-4-2 nowadays, he rarely has two strikers on the field at the same time (except for when his side is losing), and in Chamakh (no comment on him) and Bendtner (no comment on him, either), he has two strikers he doesn't even play.

I fear that this transfer may just be a facade to distract from the club's failure to land big players so far this summer. The move, though, won't hurt Arsenal branding in Asia.

Owen Hargreaves

Transfer Type: Transfer (Free)

Proposed Destination: Manchester City

Reason: This reported move by City for Owen Hargreaves is a bit of a strange one. The former United player has hardly played a competitive match in three years and has a history of contracting unfortunate injuries.

Add to that, City already have a wealth of defensive midfield talent in Nigel De Jong, Yaya Toure and Gareth Barry. If your biggest rivals let him go willingly, do you really want him? 

Yossi Benayoun

Transfer Type: Transfer

Proposed Destination: Arsenal

Reason: The former Liverpool midfielder is hard-working, skillful, and at times brilliant.

However, the big question for Arsene Wenger to try to answer is why Benayoun failed to hold down a place at Liverpool and now at Chelsea.

Florent Malouda

Transfer Type: Transfer

Proposed Destination: Arsenal

Worse For: Arsenal

Reason: This proposed deal reminds me of the Andrei Arshavin situation. In buying Arshavin, Arsene Wenger believed he was getting a seasoned match winner who would bring his young side together, giving them an edge in the title race.

Well, Arshavin has failed to launch, and I fear the same would happen to Florent Malouda. Malouda's temperament is a bit suspect, he will deflect blame onto his teammates (Arsenal and their young squad most certainly do not need that), and he is 31 years old.

Long-term solutions Arsene, not short-term fixes.

Giovani Dos Santos

Transfer Type: Transfer

Proposed Destination: Wigan

Reason: You don't go from Barcelona to Ipswich Town in less than two years unless there's something very wrong somewhere.

Not favored by Harry Redknapp at Tottenham, Dos Santos has been sent anywhere and everywhere on loan. Now, Wigan Athletic have emerged as suitors for the Mexican.

Niklas Bendtner

Transfer Type: Transfer

Proposed Destination: Everton

Worse For: Everton

Reason: Everton's money woes have been all over the news lately and so have reports of manager David Moyes' interest in Arsenal's Niklas Bendtner.

I say save whatever money you have, David.

Joe Cole

Transfer Type: Transfer

Proposed Destination: Lille, QPR or Tottenham.

Reason: While it may turn out to be a great move to land a "lauded" player like Joe Cole, it's hard to do anything but doubt just how good the player really is.

Remember Jermaine Pennant? I think the same applies here. Cole is currently in talks to join French side Lille on a season-long loan, and the proof of the pudding will be in how many games he plays for them.

My guess is very few.