"There were many various facets of harassment, with one common purpose: to threaten and frighten the complainant," he said.
During the trial, the court heard how that occurred when the man received threatening text messages, a sex toy in the mail, photos of himself defaced with phallic images and his phone number peppered around a gay meeting place.
But defence counsel Anne Stevens said it was not her client who was obsessive but the complainant, who also has name suppression.
"He has the obsession that [the defendant] is harassing him and has gone to extraordinary lengths to put him in that position," she said.
Stevens criticised the circumstantial evidence of the Crown and said some of it simply did not make sense.
The alleged animosity between the two men originated on June 14, 2012, when the defendant parked outside the complainant's workplace, blocking a rear entrance.
It led to a confrontation between the pair over a $40 ticket, however when giving evidence, each painted the other as the aggressor.
The state employee parked in a similar spot the next day which resulted in an angry text from the businessman - "clever parking dick head" - and a Facebook post related to the incident.
"The defendant took this entire parking dispute very seriously and this was the genesis of the offending. The defendant had become invested in his dislike of the complainant," McClenaghan.
But Stevens questioned why her client would feel aggrieved when he wrote to the Dunedin City Council which eventually waived the ticket.
In February 2015, police searched the defendant's property where they found a handwritten note in his car's central console.
"The smoking gun," the Crown called it.
On the paper was an email address very similar to one used to set up a fake homosexual internet dating profile using the complainant's photo.
There was also a phone number, from which the man had received abusive text messages, and the letters "NZD", which McClenaghan said referred to the website New Zealand Dating where the complainant's contact details were posted.
The forensic electronic data found on the defendant's computer was "the nail in the coffin", the Crown suggested.
On two occasions, the man had saved numerous Facebook photos of the business owner, some of which included his family.
"It was an unhealthy, obsessive and peculiar interest in a man he once had a parking dispute with," McClenaghan said.
Stevens cast doubt on the significance of the note found in her client's car.
If he was the supposed creator of the dating profile, why did he have the wrong email address and why would he have to write down his own phone number, she asked.
The defendant's explanation was that he had received the information in an anonymous text message and had written it down because he was unsure what it meant.
In reference to the photos on her client's computer Mrs Stevens noted that some of them had been deleted.
"It's not something he brooded on and kept, he just got rid of it," she said.
The trial also had heard about the defendant's work locker, wallpapered with hand-drawn pictures of penises.
The Crown said that could be linked to the fact the complainant had been sent a photo of himself covered with similar graffiti.
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Stevens pointed to the fact one of the defendant's friends had taken responsibility for the lewd artwork and rubbished the suggestion it linked her client to the alleged harassment.
"Such puerile and distinctly schoolboy antics were conducted in private spaces," she said.
It did not amount to circumstantial evidence against her client, Mrs Stevens said.
Judge Paul Kellar will deliver his verdicts on April 20.
"It's not going to be an easy task," he said.
