Jordan angrily claimed his UK insurance policy allowed him to drive the English-registered Mercedes when stopped by Gardaí.
But Judge Desmond Zaidan threw out the argument, calling it "embarrassing" and saying the documents provided "do not under any circumstances provide any insurance for Troy Jordan."
Called to the witness box, Jordan had told the judge: "With all due respect, I pay taxes and insurance like everyone else."
He said the policy had been accepted by other Gardaí but this time when he went to Naas garda station to show his documents the officers just wanted to make fun of him.
Jordan said there were four Gardaí at the hatch and they would not accept the paperwork he brought in.
"They were there for entertainment. They were waiting for a reaction from me," he claimed.
He insisted his open insurance policy was valid and allowed him to drive any car in both the UK and the Republic of Ireland.
At one point he apologised when the judge told him to answer the questions being put to him by the prosecuting garda, Inspector Paul Reilly.
"Keep your apology, just answer the question," said Judge Zaidan.
Jordan explained he had borrowed the English-reg Mercedes because there was a problem with his own car.
Garage owner Philip Johnson said he loaned the car to Jordan because he thought he would be insured on it through his own UK policy.
He was asked by the judge if he had come to court to "help a friend in need" and asked if he was trying to pervert the course of justice.
Johnson said "no" and that as far as he was concerned, Jordan's insurance policy had provided him with cover.
Judge Zaidan later said he was asking Gardaí to look into this issue.
When Jordan was stopped in the car at Prosperous Road in Clane, Co Kildare on May 19, 2020, he told Garda Darren Moulton that a man based in the UK was the owner of the Mercedes 350.
In court this week, Jordan said his good friend Glen Donoghue had in fact bought the car, and in turn had sold it on to Philip Johnson whose business is based in Bluebell, Dublin.
There was no address on the insurance policy handed into court, but he had given his address at the time as River Road, Allenwood, Co Kildare.
He said he had been staying there at the time when the country was in lockdown, but asked: "What has that got to do with my insurance?"
After the two-hour trial, Judge Zaidan said that during Jordan's "ranting" he may have said something to keep him out of prison when he had said he believed himself to be insured.
"The whole thing does not add up," the judge said.
He convicted Jordan for driving without insurance and failing to produce documents at a garda station within the required time period.
Counsel for Jordan, Ms Aisling Murphy, described him as a father of two, now back living in Ireland, and said he is not working.
Jordan recently suffered a heart attack and had to have a stent inserted.
Ms Murphy added that he is living with his partner and they "co-parent" their children.
Judge Zaidan said while he was treating Jordan as a first-time offender with regard to having no insurance, it was "not a carte blanche not to go to prison."
The judge imposed a five month sentence and disqualified Jordan from driving for four years.
After paying a bond of €400 ahead of an appeal against the sentence, Jordan walked free from the court.
Jordan has previously been closely linked to some of Ireland's most notorious criminal figures, including John Gilligan and Martin 'The Viper' Foley.
He was twice arrested by gardai investigating the murder of Latvian woman Baiba Saulite in Swords in 2006, but he was never a suspect in the case.
Along with his old pal Foley, Jordan started The Viper Debt Recovery and Repossession Services in 2005, although he resigned as a director in June 2010.
During her unsuccessful legal battle with the Criminal Assets Bureau (CAB), Geraldine Gilligan told the High Court in 2008 that her only income was €5,000 a year she received from Jordan "for grass".
Previously, Jordan has described himself as a horse breeder in his own legal battles with the CAB.
He is currently challenging a €800,000 demand from the Bureau and has taken his case to the Supreme Court.
Jordan also filed for bankruptcy in the United Kingdom in 2013 but this was later annulled, allowing creditors, including CAB, to go after his assets.
He applied for bankruptcy in England again and court records show he was successful in November 2014 in which he listed his occupation as a horse trader and horse breeder.
Despite being linked to various underworld figures, Jordan has never been convicted of any serious crime.
Among his 14 convictions listed in Naas District Court this week were illegal parking, drinking after-hours and having no tax displayed on a vehicle.