Do we do it early or late?

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History shows that the earlier the better. Players get a full pre-season and time to bond with the squad and improve team chemistry.

Younger players in particular benefit from having that stability early on.

The later you leave it, the more the upper hand goes from the buyer to the seller

Not at all. Lloris is a great example of the opposite happening. We bid early they wanted more, we walked away, they came back saying they'd accept the offer and Levy stuck the boot in changing the conditions to be even more favourable to us. Every situation is different and a money club coming in and trumping you is always a risk as are many other factors in a long negotiation. So obviously it's preferable to get in early but when you're trying to catch up on teams who have greater resources than you, you have to maximise them and that means being patient and gambling on missing out on players rather than overpaying.
 
Unless the player has a year or less on his contract, no club ever has to sell, there are plenty that have to buy.
 
Again, what is overpaying? It can be very subjective. What a player is worth to one side can be very different to his value to another.

If a player is that missing piece that your side had been looking for - The one who brings the balance to your team that was missing, then who is to say that you overpaid?
 
Unless the player has a year or less on his contract, no club ever has to sell, there are plenty that have to buy.

Equally they don't have to buy that one player either.

Realistically though it's a balance and saying that no club has to sell unless the player is in the last year of his contract must mean you've been living under a rock :D

Again, what is overpaying? It can be very subjective. What a player is worth to one side can be very different to his value to another.

If a player is that missing piece that your side had been looking for - The one who brings the balance to your team that was missing, then who is to say that you overpaid?

I'd say you're overpaying if you pay more than what you deem a reasonable price. I'm sure economists can define what the meaning of "reasonable price" is and tell you that overpaying can't exist but if we've got our sensible heads on I'm sure we can all work out when a side has overpaid.
 
A marquee signing early doors signals our intent: It makes Bale think harder before leaving and also tells other agents/players that we are no longer ****ing about. Sadly I think, on the balance of probability, that we are still ****ing about.