LONDON — They call him “Failing Grayling.”
While the trials, tribulations and humiliations of Prime Minister Theresa May have occupied center stage in the carnival of British politics, Chris Grayling has starred in a black comedy sideshow of his own. He has bumbled his way from one government post to another, accused of making a hash of each, and becoming a byword for haplessness in a golden age of political blundering in Britain.
To take one of his most recent missteps, as transport minister trying to guard against the chaos that could accompany Britain’s withdrawal from the European Union, he awarded an $18 million contract for extra ferries to handle cross-channel trade — to a company that owned no ferries.
And it didn’t end there. This past week, the government was forced to cough up 33 million pounds, about $44 million, to settle a lawsuitbrought by Eurotunnel, which complained that it was unfairly prevented from bidding on the ferry contracts, which were negotiated in secret.
While the ferry fiasco was unfolding, Mr. Grayling organized a spectacularly ineffectual demonstration of Britain’s ability to deal with the backups of truck traffic expected in a no-deal Brexit. Those traffic jams could contain thousands of trucks, but for the test, he called for just 150, and only 89 turned up.
On Friday, the opposition Labour Party chimed in with a reportclaiming that Mr. Grayling’s various misadventures — 12 in all — had cost British taxpayers 2.7 billion pounds, or $3.6 billion.
“If anyone was to read the most rudimentary audit about the effects of his time in office on the things he’s supposed to be running, he’d have been out years ago,” said Ian Dunt, the author of “Brexit: What the Hell Happens Now.” “But that’s not the manner in which the country is currently being run.”
While Mr. Grayling’s survival in the leadership has baffled many Britons, the reason, analysts say, is simple: Brexit. He is a rare breed of Conservative politician, one who is both a loyalist of Prime Minister Theresa May and a strongly pro-Brexit campaigner, but without the ideological baggage of the far right. Until Brexit happens, the combination makes him virtually impossible to fire.
“The lot of Brexiteers who are willing to work with Theresa May and aren’t bonkers is quite small,” said Rob Ford, a politics professor at the University of Manchester. “And one can argue he’s incompetent, but he’s not a flaming ideologue.”
A former BBC producer and public relations consultant, Mr. Grayling got his start when the Conservative Party chose him in 2001 to run for a seat the party had held since 1885. Charlie Mansell, the sacrificial lamb put up by Labour to run against him, said that with victory assured, Mr. Grayling did not appear to see much reason to actually campaign for the seat.
“It was almost like, ‘This is a historically Conservative seat, and I’m inheriting it,’ ” Mr. Mansell said of Mr. Grayling. “He didn’t really pitch anything on his expertise or skill set at the time.”
Retelling the story of Mr. Grayling’s mistakes has become a cottage industry in Westminster political circles. At the 2009 Conservative Party conference, he called a major personnel choice by David Cameron, then party leader, a “political gimmick,” thinking that Labour had made the appointment.
Starting in 2012, as the first justice secretary in 400-plus years without a law degree, he introduced changes that threw the legal system into an uproar. He banned books in prisons, partly privatized probationand cut lawyers’ fees for criminal legal aid by nearly 18 percent, decimating the profession. His successor from the same party, Michael Gove, promptly reversed many of the measures.
But the horrid pay and huge caseloads scared off a generation of lawyers, said Richard Miller, the head of justice at the Law Society.
“We’ve not quite yet got to the stage where someone has asked for a lawyer in a police station and they haven’t been able to get one, but we’ve come very close,” he said.
At the Justice Ministry, Mr. Grayling did not show enough concern for principles like keeping some judicial matters in public view or giving people access to courts in their communities, said Simon Hughes, who worked for part of the same period as a justice minister from the centrist Liberal Democrats. His office endlessly delayed answering parliamentary questions while political advisers hashed out the right answers, Mr. Hughes said.
“He saw everything through a very party-political optic,” Mr. Hughes said.
His flagging political profile got a lift when, after backing Brexit in the 2016 referendum campaign, he ran Mrs. May’s campaign for party leader. Having the support of a Brexiteer was crucial for Mrs. May, who had backed staying in the European Union.
He was also popular on the right for comments disavowed by lawmakers of his own party, like saying in 2010 that Christian bed-and-breakfast owners should be able to refuse gay guests. Given Mrs. May’s political fragility, analysts said, she has decided not to fire Mr. Grayling and risk the upheaval of another cabinet reshuffle.
“It is the very old story of people’s government positions being defined by their function within the Conservative Party,” said Mr. Dunt, “rather than their capacity to deliver on the thing they’re ostensibly in charge of.”
As transportation secretary, he has been trailed by calls for his resignation. He introduced new railway timetables last spring, only for hundreds of trains to be canceled each day on certain lines. A review found that Mr. Grayling had been warned weeks in advance of the impending chaos, and yet “nobody took charge.”
Brexit created more difficulties. A no-deal Brexit would mean severing longstanding agreements controlling how trucks and ferries cross between Britain and the rest of Europe. The Transportation Ministry tried to prepare by putting out a call for contracts for backup ferry operators, but it got many fewer bids than it expected, among them one from the ferryless ferry company, transportation experts said.
Mr. Grayling insisted he was supporting a start-up British business, even after it came out that the company had copied its terms of service from a takeout food website. He had to cancel the contract last month after the company’s financial backer withdrew, leaving the government out the 800,000 pounds, around $1 million, it had paid consultants.
“If you’re planning for a no-deal scenario, you’ve got to take risks, I guess, and this is what happens,” said Andrew Forster, the editor of Local Transport Today. “I don’t see how you can blame Chris Grayling for that situation.”
“Once Chris Grayling comes in, you can sell almost any article on the basis of just, ‘Look at what this guy has monstrously messed up now,’ ” Mr. Dunt said. “People really enjoy disliking him.”