Jim Justice, the businessman-turned-politician governor of West Virginia, has been pursued in court for years by banks, governments, business partners and former employees for millions of dollars in unmet obligations.

And for a long time, Mr. Justice and his family’s companies have managed to stave off one threat after another with wily legal tactics notably at odds with the aw-shucks persona that has endeared him to so many West Virginians. On Tuesday, he is heavily favored to win the Republican Senate primary and cruise to victory in the general election, especially after the departure of the Democratic incumbent, Joe Manchin III.

But now, as he wraps up his second term as governor and campaigns for a seat in the U.S. Senate, things are looking dicier. Much like Donald J. Trump, with whom he is often compared — with whom he often compares himself — Mr. Justice has faced a barrage of costly judgments and legal setbacks.

And this time, there may be too many, some suspect, for Mr. Justice, 73, and his family to fend them all off.

“It’s a simple matter of math,” said Steven New, a lawyer in Mr. Justice’s childhood hometown, Beckley, W.Va., who, like many lawyers in coal country, has tangled with Justice companies.

Mr. Justice and his scores of businesses would be able to handle some of these potential multimillion-dollar judgments in isolation, Mr. New said. But “when you add it all up, and put the judgments together close in time, it would appear he doesn’t have enough,” he said.

The son of a coal magnate, Mr. Justice took over the family business in 1993 and expanded its interests beyond coal, with acquisitions in agriculture and high-end hospitality. Like many sprawling enterprises, the Justice companies have taken on prodigious debts. But they have also taken on a reputation for not paying them — and that may be catching up to them.

A bank in neighboring Virginia that has served the Justice family for decades has begun the process of collecting on more than $300 million in defaulted loans. Some of the family business’s prized assets, chief among them the 246-year-old Greenbrier resort, are in the bank’s sights, and collections on the governor’s personal bank accounts and even his house are now a possibility. Efforts have already been underway in Virginia to seize properties belonging to Mr. Justice’s son, James C. Justice III, the president of the family companies.

In West Virginia, the tax authorities have placed liens on Greenbrier properties for millions in unpaid taxes, only months after auctioning off tax-delinquent properties owned by the governor elsewhere in the state.

Collecting on such substantial debt has pitted creditors against one another, at times to the Justices’ benefit. One bank sued Mr. Justice along with a number of banks last month after discovering that the collateral for one of its loans, some land near the Greenbrier, had also been pledged to a host of other lenders.

In a separate case, a federal judge forced the Justice-owned coal business to hand over a company helicopter to one creditor owed millions of dollars, which in turn agreed to share the proceeds of the helicopter’s sale with another creditor, also owed millions. And still, the suits, judgments and collection efforts keep piling up.

Neither the governor’s office nor lawyers for the Justice companies responded to questions. When asked about the growing mound of business troubles, Mr. Justice has repeatedly said that the daily operations of his companies are overseen by his children, and that he is focused on his duties as governor.

“There’s no way on earth that I’m going to take one second of focus off of what my job has been since day one,” he told reporters in February. “I’ve put up with this nonsense the whole time I’ve been here and everything. But absolutely, there’s no way I’ve taken my eye off the ball.”

The most serious of Mr. Justice’s troubles concerns Carter Bank and Trust, a regional bank based in southern Virginia. Carter Bank had been lending to the Justice family for decades, at one point extending roughly $775 million in loans to the Justice businesses, more than a quarter of the bank’s total net loans at the time.

Justice companies had been steadily paying that down, but in April, they defaulted on the remainder of that debt — $302 million in loans that had been personally guaranteed by the governor and members of his family. The bank demanded immediate repayment.

For the Justices, this was — as described in a deposition last summer by Mr. Justice’s son — a “mega crisis.” In November, the governor, his family and more than a dozen of their businesses sued the bank in federal court for a billion dollars, claiming that Carter Bank had engaged in unfair and coercive tactics that made it impossible to pay off the loans.

The suit against the bank did not slow things down. In January, a judge in a Virginia state court sided with Carter Bank, and the bank wasted no time starting the collections process.

The Justice companies took the case to the Court of Appeals of Virginia, saying that they could not pay the security bond, which could range from $25 million to well over $300 million and would stop the collections process. The court said it could not halt the collection effort.

In the meantime, the bank announced that it was auctioning off the Justice-owned Greenbrier Sporting Club, much to the shock and consternation of the club’s members, many of whom own multimillion-dollar homes near the club’s golf course.

That auction is being challenged in court, and an April hearing was postponed as discussions continue “in an effort to reach a resolution that might address all parties’ concerns,” a lawyer for Carter Bank said in a filing.

But the prospect of losing the sporting club portended a threat to the Justice empire’s crown jewel: the Greenbrier Resort. Mr. Justice’s decision to buy it out of bankruptcy in 2009 made him a state hero, and since then, the resort, which is appraised at well over half a billion dollars, has hosted Republican congressional retreats, pro football training camps and big-money golf tournaments, including one for LIV Golf, the league created by Saudi Arabia’s sovereign wealth fund.

It is also among Carter Bank’s collateral, and not just Carter’s: A loan for up to $50 million from JPMorgan Chase to Mr. Justice is also partially secured by the Greenbrier. Legal matters involving the Justice businesses often reveal a tangle of overlapping liabilities, and the fight with Carter Bank is no exception. In February, the Justice empire’s biggest creditor, Credit Suisse, stepped in and sued Carter Bank. Credit Suisse, which is owed about $850 million, says in its suit that Carter Bank’s collection efforts have made it harder for Credit Suisse to collect its own debt from the Justice businesses.

Lawyers for Justice-owned businesses have frequently claimed that companies being sued can’t pay because they simply have no money. But an array of plaintiffs have argued that this is a feint: that Justice officials quietly empty company accounts being targeted by creditors and move the funds to other accounts, frustrating efforts to collect on debts.

A federal magistrate in Kentucky, where one company has for years been trying to collect on a judgment in the tens of millions, has called the Justice companies’ moves to avoid turning over financial information “the most egregious litigation misconduct” he has ever encountered on the bench. The federal district judge overseeing that case is now weighing whether to hold senior Justice company officials in contempt.

As these threats pile up, Mr. Justice insists that this is all a distraction. On his federal candidate disclosure form, he listed assets valued up to around $2 billion and liabilities at less than $110 million; this list, however, does not include any Carter Bank or Credit Suisse loans, where his companies were the borrower and he was a guarantor.

Routinely, he says that all will be right in the end.

“Our family’s built an empire of stuff that employs lots and lots of people,” Mr. Justice said in a news briefing. “At the end of the day, it all seems to work out.”

His creditors might not agree with that.

Thomas Link, 59, who owns a small excavating business, was hired to perform some work for Justice-owned businesses in 2021. People told him he would regret doing business with the Justices, but, he said, he was approached by the governor himself. Several months later, Mr. Link was broke.

“‘I told you so’: that’s all I heard,” he said.

On April 24, after a year and a half of litigation, the Justice company settled with Mr. Link, agreeing to pay him a fraction of the hundreds of thousands he says he was owed. The company defaulted on the first settlement payment.