However, it's unlikely that he has ever had to deal with a caller like Jeffrey, who on Monday refused to believe that the ferry contract given to a company with no ferries was still intact despite it being cancelled on Saturday.
The government had handed out the £13.8 million deal to Seabourne Freight in January but it collapsed in just over a month after the company's major backer had withdrawn its support, leading to calls for transport secretary, Chris Grayling to resign.
However, when calling the station, Jeffrey had seemingly managed to avoid or ignore that story and argued that the deal hadn't 'fallen apart.' Before he got to that point, O'Brien asked Jeffrey why Grayling had agreed to the deal.
He [Grayling] had done the deal because any prudent and proper government, be it Labour, Conservative, Lib Dem, whoever is in government has to do what is called a 'contingency'.
O'Brien then interjects and asks that if Grayling was "prudent and proper, then why has the deal fallen apart?" An adamant. Jeffrey replies:
It hasn't fallen apart, James, it's purely and simply...
O'Brien has to stop him there and asks him to refer to the evidence that the deal is still in place and hasn't 'fallen apart.' This didn't go too well.
I don't know what sort of education you got James but you clearly don't have any manners. I haven't interrupted you once.
Just refer me to the evidence that the deal is still in place?
An already flustered and aghast Jeffrey replies:
Excuse me, Sir?
O'Brien then has to lay out exactly what has happened in regards to the story:
You're excused. Now tell me where you're getting the evidence from. You just said the deal was still in place, the one that was announced on Saturday morning to no longer be in place.
I've been on air for two hours I might have missed the news. Where did you get the information that the deal was still in place?
O'Brien reiterates this question numerous times throughout the call and Jeffrey simply cannot give him an answer and replies by telling him that he is 'rude' and that he cannot wait until the UK leaves the EU so that people like him 'will stop moaning.'
Eventually, Jeffrey gets so bored with being asked the question he calls O'Brien "a muppet" and hangs up live on air.
O'Brien then tries to sum up the conversation in the best way that he can.
That my friends is Brexit, so by now, by all means, conclude that Jeffrey has been selected for his appalling inability to process even the simplest of facts.
Conclude that Jeffrey is possibly Matt Lucas or Sir Ben Kingsley in disguise, deploying his unparalleled thespian skills to come in and fit my agenda of proving that all people like Jeffrey aren't really good at anything.
Except, as he said, looking forward to other people's misfortune. In this case, I will be upset if we crash out of the European Union because poorly educated people, who haven't got the insulation of financial security are going to get absolutely crucified.