Stephen Hunt failed in his High Court campaign to retake ownership the Victorian pier at Colwyn Bay.
Mr Justice Morgan said the pier was unsafe, in danger of collapsing into the sea at any moment and had been valued at "minus" £600,000 to £1 million.
Hunt was in no financial position to restore the derelict pier and Conwy County Borough Council had already won planning permission to demolish it, the judge said.
Mr Justice Morgan said that granting Hunt ownership would be of little or no benefit to him, other than simply "nuisance value".
Hunt paid £100,000 for the pier in 2003 with the intention of restoring it.
However, it was transferred to the Crown following bankruptcy proceedings against him and Conwy said it had bought it for £36,000 in 2012.
Hunt - whose attitude to Conwy, the judge said, was "deeply hostile" - nevertheless argued that the pier, or at least part of it, should now be 'vested' in him.
Before the pier was shut to the public in 2012, he had a "dwelling house" in the corner of its pavilion and there was no dispute that that gave him rights.
Mr Justice Morgan accepted that he had the power to award ownership of the pier, or at least the dwelling house, to Mr Hunt.
But he added that, by 2012, the dwelling house was probably already "infested by pigeons" and in a very poor condition.
Unoccupied, it was likely to have deteriorated further since then and was now probably uninhabitable, he added.
Even if Hunt was declared its owner, he could not live in it and could only get access to it via the dangerous pier.
And the judge said that, if the pier collapsed, the businessman would be left owning nothing more than "part of the airspace many feet above the beach".
Most of the pier's steelwork had already failed by 2010 and it was now "in a dangerous condition and could collapse at any moment", the court in London heard.
Conwy was spending £100,000-a-year keeping it safe and, having obtained planning consent, all it needed now was listed building consent before demolition could go ahead.
Granting the businessman what he wanted would bring him only "nuisance value" and the judge said that would not be in the public interest.
And the judge ruled: "I therefore conclude that there are good reasons for refusing to make a vesting order of either the dwelling house alone or of the whole of the pier.
"The pier is now on the point of collapse. Conwy has clear plans to demolish it. Mr Hunt has in effect no plans of his own for the pier or the dwelling house."
Hunt v Withinshaw. Case Number: OCJ 70015/ 15 of 2008