Can a GOP Candidate, Who Supported Trump and Democrats, Be New York’s Next Attorney General?

Growing up on Buffalo’s rough and often neglected East Side, Keith H. Wofford recalled many crisp autumn Sundays spent with his father bonding over the Bills, following the team’s losses and wins on the radio.

Tickets to football games were not in the family’s budget: His father, John Wofford, worked at the nearby Chevrolet factory for 32 years, and his mother, Ruby, picked up odd jobs in retail to bring in extra income. But what the Woffords lacked in money, they made up for in expectations for their two sons.

“They always had an incredible amount of confidence in us,” Wofford, 49, said in an interview. “They made very clear that they didn’t see any limitations.”

Wofford held tight to that ideal as he left high school as a 17-year-old junior to attend Harvard University on a scholarship. Seven years later, he graduated from Harvard Law School. Last year, Wofford earned at least $4.3 million as a partner overseeing 300 lawyers and 700 employees at the New York office of international law firm Ropes & Gray LLP, according to financial disclosure forms.

Now he’s the Republican nominee for state attorney general in New York, vying to become one of the most powerful law enforcement officials in the country. “How many guys who work at a white shoe law firm had dads who had a union job?” asked C. Teo Balbach, 50, chief executive of a software firm who grew up in Buffalo and played intramural rugby at Harvard with Wofford.

“He’s a real hard worker and grinder, and that comes from that upbringing where you come from a middle-class family in a difficult neighborhood and you don’t take anything for granted,” Balbach added.

In many ways, Wofford, who, with his wife Marla, has a 14-year-old daughter and an 11-year-old son, is somewhat of a study in contradictions.

He’s the first black candidate to receive the Republican nomination for attorney general in New York, yet his parents were lifelong Democrats. Wofford is the only statewide Republican candidate who would admit to voting for President Donald Trump but he has also donated money to Democrats, including Kenneth P. Thompson, the former Brooklyn district attorney, and Mayor Bill de Blasio. (Wofford now says that he regrets making the donation to the mayor.)

His campaign staff is stocked with well-known Republican operatives, and wealthy donors have filled his campaign’s coffers with enough money to fund a $3 million statewide television and digital ad buy. Despite the publicity push, Wofford was unknown to 86 percent of voters in a recent Siena College poll.

With a quick shove of his glasses above the ridge of his nose, Wofford, who described himself as a nerd while growing up, dismisses it all. “I don’t want to be limited by whatever someone else’s preconception is about what I’m supposed to be doing,” he said.

If he expects to defeat the heavily favored Democratic nominee, Letitia James, the New York City public advocate, Wofford must ignore the presumption that he’s likely to lose on Election Day. Democrats outnumber Republicans in New York by a more than 2-to-1 margin, and a Republican has not won statewide office since Gov. George E. Pataki was elected to a third term in 2002. James has a 14-point lead, according to the Siena poll.

Adding to those difficulties is Wofford’s lack of a political identity.

Bijoy Datta, chairman of the Broome County Republican Committee, heard Wofford’s name floated as a potential candidate just weeks before the Republican convention in May. They didn’t meet in person until the night before the convention — a fact that does not deter Datta from supporting Wofford.

“We live in a time when not being a politician is a good thing,” Datta said.

Opponents of James accused her of being too close to Gov. Andrew M. Cuomo, criticism that Republican strategists say will hurt her. All three of James’ primary opponents have since endorsed her, but some Democrats and independent voters may be looking for a different option, Datta said.

Wofford is neck and neck with James in terms of fundraising, especially after she spent heavily to win the primary. And Wofford’s upstate roots and his experience working and living in the city give him statewide appeal, Republican strategists say.

James portrays Wofford as a wealthy, out-of-touch and ardent Trump supporter in a state where the president and his policies are deeply unpopular. As in the Democratic primary, James has made standing up to Trump a central campaign plank. Wofford has taken a different tack, focusing on efforts to root out corruption at the state level so that taxpayer money can be spent more effectively.

“You have people who are intent on suing the president from the moment he took office,” Wofford said. “We’ve had 12 years of people being led off in jumpsuits and the people of the state government have not lifted a finger.”

Wofford said he would need to see the underlying evidence before deciding whether Attorney General Barbara D. Underwood’s lawsuit accusing Trump of using his charitable foundation for political and business purposes is worth pursuing. He “doesn’t have a view” on The New York Times’ investigative piece showing that Trump engaged in “dubious tax schemes” and “instances of outright fraud” in the transfer of his father’s wealth, but “you have to look,” Wofford said, because of the millions of dollars in taxpayer money at stake. Democratic candidates criticized James for saying that she did not want to be known as the “Sheriff on Wall Street,” a sobriquet earned by Eliot I. Spitzer, the former attorney general and former governor of New York, for using the Martin Act, an expansive state law, to prosecute financial fraud.

Wofford said he believes that overzealous prosecutors are using the Martin Act to drive businesses out of New York. An attorney general in Texas should not be “hostile” to the energy industry, Wofford said by way of example.

“You enforce the law against the banking and investment management industry but you also have to be cognizant that they’re paying huge taxes in this state,” Wofford said.

This month, top Republican donors, including Maurice R. Greenberg, former chief executive of American International Group, held a fundraiser for Wofford. Greenberg, who paid a $9 million civil settlement for accounting fraud last year, is seeking to curtail the Martin Act.

“Just like Trump and congressional Republicans,” Wofford wants to let “Wall Street off scot-free,” said Jack Sterne, a spokesman for James.

Other issues facing Wofford should he win are potential conflicts of interests from his law practice. His firm has represented Purdue Pharma, a maker of opioids. Underwood and Cuomo announced a lawsuit against the company in May over its marketing of the pain drug.

Wofford was also the lawyer for Knighthead Capital Management, LLC, a hedge fund that was criticized for its handling of Puerto Rico’s debt after Hurricane Maria. Cuomo has also threatened to sue the federal government over its response to the hurricane.

Wofford said that he has never personally represented Purdue Pharma and said he will sever all ties with his firm if elected. He has announced a plan that would use money from any opioids lawsuit settlements to fund addiction treatment. Wofford said the criticism about him is indicative of James’ “hyperpartisan” attitude, and he sought to distinguish himself from her by characterizing himself as an outsider.

“Being on the wrong side of the tracks in Buffalo,” Wofford said, “is about as far from insider as you can get.”

His success as a lawyer, however, did allow him one heartfelt opportunity: In his father’s last years, Wofford returned to Buffalo, and during football season, they would bond again over Bills games — but in person, at the stadium, as a season-ticket holder.