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SAN ANTONIO — When Henry Cuellar’s district was redrawn in 2021, it picked up tens of thousands of more people in San Antonio, giving the city more influence in his hotly contested South Texas primary.

And the city spoke, with Bexar County picking his progressive challenger, Jessica Cisneros, by massive margins in the primary and runoff. Even as he narrowly defeated Cisneros overall, Cuellar acknowledged to reporters on the night of the runoff that he needed to “go spend time in the areas that need to get to know me better.”

He has appeared to make good on that promise, especially when it comes to organized labor in San Antonio. After labor groups vocally supported Cisneros, Cuellar has been working to repair a relationship that was strained at best in some cases.

“I take full responsibility and I’ve said this more than once: I should’ve done a better job at outreaching,” Cuellar said during a meeting with labor leaders here this month. “I think after several good meetings of having very frank discussions … we’re now moving [forward] and I’m trying to find ways I can be of assistance.”

Cuellar’s latest overture came last week, when he introduced a bill to provide child care stipends for union apprenticeship programs. The legislation is endorsed by a host of building trades unions.

It’s one of several moves Cuellar, known as one of the most moderate Democrats in Congress, has made in the past year in an attempt to show unions he is listening to them more, even if they still do not see eye-to-eye on every issue.

“Like any relationship, there’s disagreements, but I think the disagreements have gotten far fewer, and ears on both sides have started to open up,” said Charles Fuentes, legislative director for the Communications Workers of America in San Antonio.

Fuentes was among four labor leaders that Cuellar convened earlier this month in downtown San Antonio to discuss the child care legislation. CWA vocally backed Cisneros in both her challenges to Cuellar, arguing at the time that Cuellar “votes with corporations and Wall Street time and time again.”

“We’d like to see more compromises on each side so that we can meet our goals,” Fuentes added, “but I look forward to this working out.”

With just under three weeks left until the end of the candidate filing period, Cuellar has not drawn a primary opponent for 2024. Cisneros has not publicly ruled out a third run, but few believe she is inclined to try again.

To be clear, there is a diverse range of labor groups in San Antonio — the state’s second most populous city — and Cuellar seems to be especially focused on the building trades unions. And whatever the group, they still do not agree on a major issue: the Protecting the Right to Organize Act, or the PRO Act, which would impose new limits and penalties for companies opposing union organizing efforts and add new protections for workers seeking to unionize.

Cuellar was the only House Democrat to vote against it in 2021.

Cuellar’s business-friendly credentials are well-known. The U.S. Chamber of Commerce backed him in both his battles against Cisneros and even aired TV ads for him in 2020 — the first time it spent significantly on behalf of a Democrat in six years.

Cuellar’s new outreach started in earnest after the 2022 primary runoff, when he was entering the general election as a new target of national Republicans. They were intent on blazing new inroads in South Texas, and Cuellar knew he needed every Democratic vote he could get out of San Antonio despite getting crushed there against Cisneros.

Bob Comeaux, a longtime labor leader in the city, said the Bexar County results “put the scare” into Cuellar and “kind of forced him to come talk to us and beg for our support.” While many of his peers remained angry at Cuellar over the PRO Act, Comeaux said he believed they had to be practical — the House Democratic majority was on the line, and Cuellar’s seat was looking pivotal to that fight.

“Some of us who have been around the block more than once, while we were not happy with him for that vote, [we] understood that we don’t punish ourselves at the same time we’re punishing him,” Comeaux said.

Cuellar ended up beating his Republican opponent, Cassy Garcia, by a wider-than-expected margin — 13 percentage points — and carried Bexar County by 16 points.

Comeaux said Cuellar’s staff has also become more receptive to labor concerns. Cuellar said he now has a staffer who “will work with not only the local unions but with the state [and] national unions.”

Cuellar has continued the outreach this year. In June, he held a roundtable with more than 60 members from over a dozen South Texas Unions. In September, he gave the keynote address at the San Antonio Central Labor Council’s Labor Day Breakfast. And last week, he introduced the bill on child-care stipends for apprenticeships, along with three Democratic colleagues.

The Apprentice-Related Child Care Act would set up a two-year, $200 million pilot program that would award grants to 10 states to provide stipends to apprentices. The stipends would be paid directly to child care providers who serve apprentices and would be at least $500 a month per child.

At the recent meeting with labor leaders, Alejandra Lopez, president of the San Antonio Alliance, said Cuellar’s support for apprentices could have a “profound impact for his district.” Fuentes said the child-care stipends would be especially meaningful, calling child care a “very, very large hurdle” for a lot of workers currently.

Dale Hanson, representing the International Brotherhood of Electrical Workers Local Union 60, said child care is a “major economic hindrance” for his fellow workers.

“A lot of us, our job sites, we start work at seven o’clock in the morning,” Hanson said. “Good luck finding a child-care place that’s going to accept infants at seven o’clock in the morning.”

As the conversation broadened, it was not long before the PRO Act came up. Fuentes said the proposal — or something similar to it — could strengthen a burgeoning labor movement and “rebalance those scales of employers and employees.”

Cuellar said he was hoping U.S. Rep. Bobby Scott, D-Va., the ranking member of the House Education and the Workforce Committee, would allow Cuellar to “make a few adjustments” to the bill and he could support it.

“We gotta find balance,” Cuellar said. “I try to find balance between labor and business.”

“If I think business is overdoing it,” Cuellar added, he will say so. Cuellar noted he signed on to a July letter supporting UPS workers’ right to collectively bargain with their employer. He said UPS was not pleased with him, but it was “the right thing to do.”

Hanson also mentioned the need for the PRO Act.

“I get it. Mr. Cuellar’s in a very tough district, and you know, balance is important,” Hanson said.

The 28th District is heavily Hispanic and stretches from the Rio Grande Valley north through Laredo to the northeast suburbs of San Antonio. It used to include about 197,000 people in Bexar County; now it has roughly 252,000, growing to a third of the district’s total population

So far, Cuellar’s only opponents for reelection are Republicans. One of them is a former staffer, Jose Sanz.

Laura Barberena, a San Antonio Democratic consultant, said she thinks Cuellar’s outreach to unions is one reason he could have a smoother primary next year. While Cisneros was a “very strong candidate,” Barberena added, her races showed how costly and personal it can be to challenge Cuellar. And the consultant noted Cuellar prevailed in 2022 despite some uniquely strong headwinds, including a still-unexplained FBI raid on his Laredo home.

“Really, if you’re gonna bring his numbers down, what more could you do?” Barberena said, adding it would be “very, very difficult” to beat Cuellar in a primary at this point.

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