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Is Daniel Levy about to take the biggest transfer gamble of his Tottenham stewardship?

The way we reward our best players with upgraded contracts virtually every year, it beats me why Alderweireld didn`t go down this line years ago when he was first offered a new contract, he`d have been quids in by now. Either his advisers are morons, or he`s gambling on getting one almighty big signing on fee, and it will have to be massive to compensate for what he`s already lost. That said, I suggest we work out what we`ve already saved and offer it to him to sign a new contract.