Jacob Windle was locked up for two and a half years after a court heard he was involved in a police chase in a stolen van during a separate incident.
The 24-year-old was also caught with three stolen motorbikes on an another occasion when police went to his home in Middleton, Leeds.
David Ward, prosecuting, told Leeds Crown Court how a Mercedes Sprinter van was stolen from outside a business premises on Dewsbury Road, Ossett, in November 2018.
Mr Ward said the van involved in a raid on HGV which was parked up overnight near to junction 21 of the M1 in Leicestershire in the early hours on December 6, 2018.
Thieves slashed through a side curtain as the driver was asleep and helped themselves to the cargo of cases of wine.
A total of 5,736 bottles were loaded onto the Mercedes van.
Windle was stopped by police in the northbound carriageway of the M1 later that day.
Windle arrested but continued to offend while on bail.
He was spotted driving another stolen Mercedes van on false number plates on the M62 in June last year.
Windle failed to stop for police officers and drove the wrong way along the westbound slip road at Junction 32 of the motorway at Castleford.
Other vehicles had to take evasive action to avoid a collision.
He was found in possession of cannabis when he was arrested.
Three stolen motorbikes worth around £7,000 were found in the garden of Windle's home when police went to his address on September 4, 2018.
The prosecutor said the vehicles had been stolen a month earlier in Bradford and Leeds.
Windle told officers he had bought the machines from a man who brought them into his street on a truck.
He claimed he had bought them because they had been offered to him at a cheap price.
He said he did not think it was suspicious despite the motorbikes not coming with any documentation.
Windle, of Acre Road, Middleton, pleaded guilty to three offences of handling stolen goods, dangerous driving, driving while disqualified, taking a vehicle without consent and possessing a class B drug.
He has previous convictions for drug and vehicle offences.
Graham O'Sullivan, mitigating, said: "He is determined to turn over a new leaf in his life."
Describing the theft of the wine from the lorry, Judge Simon Batiste said: "It had all the hallmarks of professional criminality."