The nickname was invented by those who believe that political mishaps seem to follow the transport secretary around.
So how does his record shape up?
While he was justice secretary, Chris Grayling oversaw the introduction of private probation contracts which were scrapped last year at a cost of £170m. He was also criticised for cuts to legal aid.
His two and a half years at the Department for Transport have been no less eventful.
The botched introduction of new train timetables caused disruption for tens of thousands of commuters.
Grayling sought to shift the focus onto industry, saying: "I don't run the railways".
But trains have proved a constant headache for the secretary of state.
There's been a lengthy industrial dispute with Southern Rail workers resulting in strikes that caused chaos for passengers.
In June last year, the East Coast Main Line was taken back into public ownership after the franchise owners ran into trouble.
The latest figures show train punctuality is now at a 13-year low, despite fares steadily increasing.
That said, sources close to the secretary of state say passenger numbers have soared in recent years and point to the rail review set up by Grayling in September.
On Brexit, Grayling has been heavily involved in contingency planning for a no-deal.
Last month his department paid lorry drivers almost £50,000 to take to the roads of Kent to rehearse what could happen if a no-deal caused backlogs at ports.
Some 150 vehicles were due to take part, but only 89 turned up - including one bin lorry.
The purpose of the exercise was to track flows of lorries around the county's roads and Grayling said, to that end, the rehearsal had been a success.
But that didn't stop accusations that the transport secretary wasn't even able to organise a traffic jam.
Given all this, many feared the worst when it emerged that one of the companies hired to provide extra ferries in the event of a no-deal Brexit didn't actually own any ships.
We've found out today that a big reason why the contract was approved with the relatively new firm Seaborne Freight was because they were being backed up by Ireland's largest shipping operation. When that company pulled the plug, Grayling axed the deal.
Sources in the Department for Transport insist no money was given to Seaborne and full due diligence was carried out prior to signing the contract.
But whichever way you frame it, today's events are not a good look for the often embattled transport secretary. Labour has called on him to resign, branding him "the worst secretary of state ever".
When, with devastating politeness, Sky's Sophy Ridge asked Grayling last month why it was that "misfortune seems to follow you", he said it was a "challenging time" for everyone in government.
There's no doubt the transport secretary has had to contend with factors that are out of his control - the impact of driver-only trains on the workforce, an increasing demand for services and the advent of drone technology.
Those close to the Surrey MP also point to Heathrow expansion as one of Grayling's successes. Others will wonder why so many "challenges" continue to land in his lap.