Nicholas Birch had been out of prison less than three weeks when the lies started again.
The 29-year-old's criminal history featured nearly 100 convictions, most of which were for serious dishonesty, stretching back to his teens.
But this was the first time he had lied to a judge.
Indeed, the Dunedin District Court heard yesterday that what Birch did had never happened before.
On March 31, 2015, the defendant stood in the Alexandra District Court claiming to be the representative of a ''successful businessman, horse trainer and philanthropist'' vouching for the criminal in the dock.
The man being sentenced by Judge Michael Crosbie at the time was Fletcher Dennis, facing a long jail term for burglary.
But in stepped Birch, offering to pay $30,000 the man owed in fines and reparation, with a job waiting for him when his sentence ended.
He told the judge he and the mystery benefactor had communicated with Dennis by letter in prison and the company saw ''great potential'' in him.
Birch explained his boss' son had been assisted in similar circumstances years earlier and wanted to help someone in the same way.
The heart-warming story resulted in Judge Crosbie shaving six months of Dennis' sentence.
But there was one problem. It was all a lie.
''What you did was you conned the judge,'' Judge Kevin Phillips said yesterday
''There was no benefactor, no employer, no hope of [the money] being paid as you promised.''
What Birch did not tell the judge was that he and Dennis had been cell mates at Otago Corrections Facility until 19 days before the incident, when the defendant was released at the end of a previous sentence.
Judge Phillips said the spiel in Alexandra was clearly premeditated.
''This is not something that he just thought up on the day ... It looks like it was done in the cells at OCF,'' he said.
''There was a deliberate lie to a district court judge. It strikes at the very heart of the process.''
Counsel Len Andersen said in researching the case, he had come up with nothing comparable.
Judge Phillips had also looked to higher court decisions for guidance in the sentencing hearing and had been stumped, too.
''I can't find any authority where someone has bareface lied to a judge,'' he said.
''There hasn't been someone such as you who had the temerity to stand in front of a sentencing judge and shamelessly lie and lie and lie.''
Birch was also convicted of three counts of driving while disqualified, all of which came within a six-week span from August last year.
Mr Andersen told the court the defendant had hired a driver to get him around while he was banned but on one trip to Christchurch in October the chauffeur allegedly deserted him.
Birch was stopped while driving back to Dunedin.
Judge Phillips said that excuse did not match up with what he told police when he was pulled over.
Birch gave a false name and claimed he had never previously been involved with the police.
His letter to the court apologising for his behaviour was treated with a similar scepticism by the judge.
''I doubt whether much of that is true,'' he said of its contents.
Birch was jailed for one year 11 months with the prospect of home detention swiftly quashed by Judge Phillips at the hearing's outset.
He was also banned from driving for 15 months.
''You hold the judicial system and the court up to ridicule,'' he said.