WASHINGTON — Joe Walsh, a conservative radio show host and a former Tea Party congressman from Illinois who is expected to announce a long shot primary challenge to President Trump in the coming days, is wooing the husband of Kellyanne Conway, Mr. Trump’s former campaign manager, for a senior role in his campaign — a signal of his intent to troll Mr. Trump into engagement with him.
Mr. Walsh met on Thursday with George T. Conway III, the prominent conservative lawyer who is married to Ms. Conway, one of Mr. Trump’s longest-serving aides. During the hourslong conversation, the two discussed strategy going forward, according to two people familiar with the conversation, and Mr. Walsh asked Mr. Conway if he would join his nascent campaign in a leading formal role.
Mr. Conway, who has gained a large following on Twitter for his increasingly virulent critiques of Mr. Trump and his mental state but who has never worked on a political campaign before, did not commit to anything, telling Mr. Walsh he would think about it, the two people said.
Mr. Walsh has virtually no chance of wresting the Republican presidential nomination away from Mr. Trump, whose poll numbers with Republicans remain consistently in the high-80s. But as a former supporter and media-trained radio show host attacking him from the right, he has an opportunity to rattle Mr. Trump with his television criticisms, and with audacious moves like trying to work with Mr. Conway, whose denunciations have personally enraged the president and his family members.
In recent days, for instance, Mr. Trump has engaged with Anthony Scaramucci, his White House communications director who lasted 11 days in the job, who has turned against his former boss and encouraged other Republicans to take a stand against him.
“I think Walsh’s plan to attack Trump for his dishonesty, amorality, instability and incompetence is absolutely the right approach, and I’ll do whatever I can to help,” Mr. Conway said in an interview, though he declined to say whether he would formally join the campaign.
Mr. Conway has been criticizing his wife’s boss for more than a year, after having supported him during the 2016 campaign, when Ms. Conway worked as Mr. Trump’s campaign manager. Now, with a re-election campaign at hand, Republicans like Mr. Conway, who view Mr. Trump as a threat to democracy and the rule of law, are facing a new reality: Rather than just hurling criticisms at Mr. Trump from the sidelines, they now have the option to support or work for a primary challenger, or a Democrat, in order to help defeat him.
It’s still not clear if Mr. Conway will leave his more comfortable perch as an armchair critic to help Mr. Walsh, whose own history of calling President Barack Obama a “Muslim” and a “traitor” have made some of his followers uncomfortable, even those who are encouraging him to challenge Mr. Trump.
In March, when Mr. Conway raised new questions about the president’s mental health and said he was a “malignant narcissist” suffering from narcissistic personality disorder, the president took the bait, responding on Twitter by calling him a “stone cold LOSER & husband from hell!”
Mr. Trump’s son Eric and his campaign manager, Brad Parscale, have also singled out Mr. Conway online for criticism. Mr. Trump and his close aides have spent less time focused on Mr. Conway in recent months, aides said, tuning him out as his criticisms that have continued unabated.
Earlier this month, Mr. Conway criticized Mr. Trump’s staff on Twitter, writing: “I love how these people who work for a rapist have no compunction about making accusations of abuse by someone who criticizes the rapist.”
Mr. Trump’s re-election campaign has dismissed Mr. Walsh’s bid as a “certain failure” and declined to comment its interest in Mr. Conway.
On the same day that Mr. Conway was meeting with Mr. Walsh, Ms. Conway headlined a “Women for Trump” event in Tampa, Fla., which drew hundreds of female supporters.