Of the dozens of speeches at the Republican National Convention last week in Milwaukee, none perhaps was as surprising — or as immediately divisive— as Teamsters President Sean O’Brien’s on the conclave’s first night.

Business groups recoiled. Many rank-and-file union members were furious. And within the labor movement’s leadership, O’Brien’s words — both soothing and challenging to the Republican Party — are still reverberating. Was the head of a union 1.3 million members strong actually flirting with former President Donald Trump, or was he surreptitiously sticking it to the party of Big Business?

Probably both.

“I, like others, wondered what he was doing,” Randi Weingarten, the president of the American Federation of Teachers and a staunch Democrat, said in an interview Thursday, “but I listened to the speech, and I was impressed that he gave not only such a pro-worker speech, but at its foundation, he said these greedy corporations are hurting us, and you can’t have it both ways, Republican Party. If you want labor’s support, you can’t just pander at election time. You have to walk the walk and give workers a chance to thrive.”

That’s not how others in unions saw it.

“O’Brien wants kinder, gentler, more patriotic bosses, and anyone that thinks he’s preaching class war is a mark,” fired back C.M. Lewis, president of the Seven Mountains AFL-CIO in Central Pennsylvania, on social media. “He heaped praise on Trump, a silver spoon-fed caricature of the corporate elite — utterly clownish.”

In response to the criticism, Teamsters officials encouraged people to read the speech. In it, O’Brien began by extending a respectful hand to Trump, who stocked his Labor Department and National Labor Relations Board with anti-union lawyers and backed a series of court cases to weaken collective bargaining.

“In light of what happened to him on Saturday, he has proven to be one tough SOB,” the Teamsters leader said, referring to the July 13 assassination attempt. He then praised other Republicans like Sen. Roger Marshall of Kansas and Sen. Josh Hawley of Missouri, who is running for reelection this year against a Democrat, Lucas Kunce, who has most of the state’s unions behind him.

Calling out big business

But once O’Brien softened the skeptical crowd, he turned to the labor part of his speech, castigating companies that stand against union organizing and that fire labor leaders for union activism. He called out Republican mainstays like the U.S. Chamber of Commerce and Business Roundtable as hypocritical: They oppose workers uniting to bargain collectively for wage and benefit improvements, he said, but they are functionally unions for big business, colluding against their workers.

And he singled out companies by name.

“Massive companies like Amazon, Uber, Lyft, and Walmart take zero responsibility for the workers they employ,” he told a hushed audience. “These companies offer no real health insurance, no retirement benefits, no paid leave, relying on underfunded public assistance. And who foots the bill? The individual taxpayer.”

The response from the Republican attendees was not good. Most stood in silence. Some walked away. Business groups were none too pleased.

“The partnership between employers and employees in the United States has produced the strongest and most resilient economy in the world,” said Michael Steel, a spokesperson for the Business Roundtable, which represents the CEOs of the nation’s largest corporations. “Attempts to pit American business and labor against each other for partisan gain make it harder for America to succeed.”

Having it both ways?

The fallout from O’Brien’s speech captures the dilemma facing organized labor as Trump emerges from his convention, and his brush with an assassin’s bullet, confident he will recapture the White House. After he stepped down from the stage, O’Brien said on CNN that President Joe Biden “is definitely the most pro-labor president we’ve ever had.” The president pushed for and then invested $36 billion in rescuing the Teamsters’ pension plan.

But that might be beside the point if Biden loses or drops his reelection bid, so do labor leaders attempt cooperation with Trump, or do they dig in and fight?

Weingarten’s answer contradicted O’Brien’s stance.

“Presidential elections are not times for games,” she said. “They are serious, and this is particularly serious. We face a choice: democracy or autocracy.”

Not an endorsement

The Teamsters are the last major union not to endorse in the presidential race, and O’Brien’s words could be parsed to either side’s advantage. Most union leaders fear that long after the substance of the speech is forgotten, the image of a burly, truck-driving union president will be heaped with others, from former pro wrestler Hulk Hogan to aging rocker Kid Rock, to attest to Trump’s working-class appeal.

“It gave the Republicans credibility,” Randy Bryce, a Wisconsin iron worker who runs a pro-union super political action committee, said of the O’Brien speech.

Still, most union members panned O’Brien’s speech. A Teamsters-owned social media account this week appeared to have gone rogue, posting, “Unions gain nothing from endorsing the racist, misogynistic, and anti-trans politics of the far right.” The post was quickly taken down, and the Teamsters declined to comment on the matter.

Trump criticizes UAW

And Trump’s call in his acceptance speech Thursday night for the United Automobile Workers to fire its aggressive and popular new president, Shawn Fain, for backing Biden and his administration’s effort to get more Americans to transition to electric vehicles underscored his contempt for labor, UAW officials said.

“America’s autoworkers aren’t the problem,” Fain declared Friday. “Our union isn’t the problem. The working class isn’t the problem. Corporate greed and the billionaires’ hero, mascot, and lap dog Donald Trump, are the problem.”

He added, “Don’t get played by this scab billionaire,” using slang for a strikebreaker.

Bryce said before the speech that he had been supportive of O’Brien’s appearance at the Republican convention, arguing to friends that the labor movement needed to take its message to people of all political persuasions. Afterward, he said that though he appreciated some of the messages, he thought it was a bad idea. Under Wisconsin’s former Republican governor, Scott Walker, public-sector unions were gutted, and mandatory union dues at union-organized employers were ended.

With Republicans favored to take control of all three branches of the federal government, “this was not the time,” Bryce said. “You have to pick one side right now. They’re out to get us.”

O’Brien’s performance has Democrats in something of a bind. O’Brien, who declined to comment, has said publicly that he requested speaking slots at both the Republican and Democratic conventions. At Trump’s insistence, the GOP agreed. The Democrats have not.

Democratic convention and Biden campaign aides said they have not yet invited any speakers for the August convention in Chicago. And unlike the Republicans, the Democrats have numerous labor leaders who would love a slot. If they gave one to O’Brien, they would feel pressure from dozens of other union presidents.

For now, Biden is confident that unions are staying with him, perhaps among the last bulwark publicly calling for him to stay in the race.

“Joe Biden knows unions built this country and the middle class,” Julie Chavez Rodriguez, the campaign manager for Biden and Vice President Kamala Harris, said in a statement. “Donald Trump will always choose big greedy corporations and anti-union extremists over the working men and women of America.”