As Michael Bloomberg edges closer to entering the Democratic race for president, he faces deep skepticism on the left over his Wall Street background and his record as New York City mayor. Those problems might be exacerbated in Pennsylvania.

In the last two federal election cycles, Bloomberg helped two high-profile Republicans win critical races in the Keystone State.

Gun-control groups backed by Bloomberg endorsed U.S. Sen. Pat Toomey in 2016 and U.S. Rep. Brian Fitzpatrick in 2018, lending weight to their pitch to voters that they were independent voices who could collaborate across the aisle. In both races, the lawmakers were trying to win over moderate swing voters, and each narrowly squeaked to reelection.

They are two of a handful of Republicans who have supported expanding background checks for gun purchases, a top Democratic priority and one Bloomberg has made a central part of his work since leaving the mayor’s office.

Still, Bloomberg’s aid for Republicans has left some Pennsylvania Democrats with a bitter taste.

“I don’t think there’s any flavor for him here,” said Philadelphia party chair Bob Brady, an ally of former Vice President Joe Biden. “He’s for Republicans. We’re not for Toomey, naturally.”

Bloomberg, who has long cast himself as a centrist who can appeal to a wide swath of moderates in both parties, was in Arkansas on Tuesday to file paperwork to ensure he gets on the primary ballot there.

His potential entry comes less than three months before the first votes in the nominating contest, in Iowa, and as some Democrats fret that Joe Biden is fading and leaving liberal Sens. Elizabeth Warren and Bernie Sanders as the party’s most likely nominees. More moderate Democrats fear those senators can’t beat President Donald Trump, prompting renewed interest from Bloomberg and former Massachusetts Gov. Deval Patrick.

Bloomberg’s endorsements and cash behind Pennsylvania Republicans "will present its problems,” said John Cordisco, chairman of the Democratic Party in Bucks County, where Fitzpatrick’s district is based. “There’s going to be a core of Democrats that are going to need to understand what prompted him to do that, and it just doesn’t remain within the borders of Bucks County. Other groups throughout Pennsylvania are going to be asking those same questions.”

Bloomberg wasn’t alone in praising Toomey and Fitzpatrick, two of the rare Republicans to support tougher gun laws. Former Democratic Rep. Gabrielle Giffords, who was gravely wounded in a mass shooting, also backed both men, along with endorsing a number of Democrats.

Gun-control groups know that bipartisan support will almost certainly be required to pass any new measures and have sought to reward the few Republicans who have crossed party lines on the issue. More broadly, Bloomberg’s political groups, Independence USA and Everytown for Gun Safety, have mostly supported Democrats, including Pennsylvania Gov. Tom Wolf and four Democratic House candidates in Pennsylvania swing districts in 2018.

“As a single-issue, nonpartisan organization, Everytown is committed to working with lawmakers who support passing stronger gun laws regardless of political party," spokesperson Taylor Maxwell said in an email. "Gun safety isn’t a right or left issue — it’s a matter of life or death.”

Ed Hozza, chairman of the Lehigh County Democrats, said he took no issue with Bloomberg’s GOP endorsements, given their connection to gun-control legislation. When he was the mayor of Whitehall, Hozza said, he joined Bloomberg’s Mayors Against Illegal Guns coalition to push for a ban on assault weapons.

“Mayor Bloomberg is known to be a consensus-builder, and [gun control] is one of the major issues coming up next year," Hozza said. "And God knows we need that today.”

But several Pennsylvania Democrats said Bloomberg would face tough questions about endorsements in highly competitive races that could have altered the broader dynamics in Congress.

After the Fitzpatrick endorsement, a Bucks County group aligned with Everytown for Gun Safety disbanded in protest.

Lt. Gov. John Fetterman, who unsuccessfully sought the Democratic nomination to challenge Toomey in 2016, sarcastically suggested that Republicans should offer to help Bloomberg.

“Here’s hoping Pat returns the solid,” Fetterman wrote in response to an Inquirer question. “Currently unaware of any other PA Democrats considering joining a potential Toomey-led groundswell.”

Bloomberg’s burgeoning campaign did not respond to requests for comment Tuesday.

Independence USA, a Bloomberg super PAC, endorsed Toomey in 2016, along with two Pennsylvania Democrats, Attorney General Josh Shapiro and Treasurer Joe Torsella. Independence USA spent almost $6 million backing Toomey, though that was a relatively small amount in the most expensive Senate race in the nation.

In 2018, Everytown endorsed Fitzpatrick in a tight Bucks County race.

Toomey won by 1.5 percentage points and Fitzpatrick won by 2.

If he does run, Bloomberg might become a natural rival to Biden among the party’s donor class, but he carries some major liabilities with the party’s base. His presence could underscore the wealth inequality and concentration of power that activists rail against. Bloomberg also oversaw controversial stop-and-frisk policing in New York that has become a symbol, for many liberals, of overly-aggressive law enforcement that has targeted minorities.

At the same time, Bloomberg has also spent heavily to support a number of major liberal goals, including tougher gun laws and fighting climate change.

In Pennsylvania, he donated $10 million to help battle the opioid epidemic. And in Philadelphia, he spent almost $845,000 to build public support for a soda tax as City Council studied it and passed it in June 2016.

Despite the tight races Toomey and Fitzpatrick won, Cordisco downplayed the impact Bloomberg might have had. He doubted most outside endorsements mean much to voters.

And he said Bloomberg’s bipartisan credentials could help him win over moderate Republicans looking for an alternative to Trump. “But he’s got to get through a primary to get the benefit of those voters,” Cordisco added.

Neil Oxman, a longtime political consultant based in Philadelphia, said most Democrats who would take issue with Bloomberg’s endorsements were never going to back him in the first place. Same for the criticism of some of his more moderate stances on criminal justice reform.

“He’s not going to get votes from the far left from people who care about that,” Oxman said.

Instead, Oxman stressed there are moderates in the Democratic Party and independents who might be intrigued by Bloomberg, who was elected as a Republican, became an independent, and currently is a registered Democrat.

Among them might be Vaughn Slater. Voting in Mount Airy last week, Slater said there are “like 100 candidates” on the Democratic side, but that he was unenthused by all of them.

Asked who he would have liked to see get into the race, Slater named Bloomberg: “He was mayor of New York City. Yes, he’s a billionaire but I think overall skill set-wise, temperament-wise, ability, he’s a guy that is just very successful in his own right and I think he would build a team of people that would basically represent the country in the best light.”

Bloomberg’s interest in a late-stage campaign emerged two days later.