Last summer, as several of President Trump’s former adversaries attempted to mend fences, he held a meeting with one of his most entrenched enemies: his former personal attorney and fixer, Michael D. Cohen.

According to anonymous sources familiar with the matter, the two held a brief but significant conversation at the president’s exclusive golf club in Bedminster, N.J. This meeting ended a years-long estrangement defined by public hostility and intense legal battles.

This encounter, which had not been previously reported, gave Mr. Cohen a way back into Mr. Trump’s inner circle and initiated a broader effort to reconcile. This outreach included a second, more extensive meeting earlier this year, as well as several phone calls to the president’s closest confidants.

Mr. Cohen’s public rhetoric has shifted dramatically. Two years after serving as the key witness in the New York criminal trial that led to Mr. Trump’s conviction for falsifying business records, Mr. Cohen has now begun publicly criticizing the prosecutors involved in that case.

In a recent interview, Mr. Cohen stated that his relationship with the president has improved in recent months, noting that Mr. Trump took notice of the liberal backlash following Cohen’s criticisms of the prosecution.

“If Donald Trump and Michael Cohen can rekindle and reconcile their past relationship, then anyone should be able to,” he remarked.

The rapprochement offers clear professional benefits for Mr. Cohen. With the apparent blessing of the White House, he is launching a radio show on WABC, a Trump-friendly station in New York. Filling the summer time slot previously held by former Gov. Andrew Cuomo, Mr. Cohen has expressed ambitions for the show to eventually be syndicated.

While other high-profile critics who sparred with the president have faced potential prosecution from the Justice Department—including former F.B.I. director James Comey and New York attorney general Letitia James—Mr. Cohen has not. Since returning to office, Mr. Trump has ceased his public attacks against him.

The White House did not respond to requests for comment.

This truce marks a surprising final act in a volatile relationship. Both men, known for their aggressive personas and tendency to lash out at opponents, have transitioned from partners to betrayers and may now return to public cooperation. While promoting his new program, Mr. Cohen suggested that Mr. Trump might appear as a guest in the coming weeks.

If his recent comments are any indication, Mr. Cohen may use his platform to undermine his previous role as a star witness. During the Manhattan district attorney’s hush-money investigation, Mr. Cohen claimed he cooperated because Mr. Trump needed to be held accountable for his “dirty deeds.” Now, Mr. Cohen, who served prison time for his role in that same deal, claims he felt “compelled and coerced” into providing the information the prosecutors sought.

Mr. Trump, who has privately expressed sympathy for Mr. Cohen’s time in prison, could leverage these new admissions to challenge the legal cases against him. His legal team has already cited Mr. Cohen’s recent remarks in court filings as part of a strategy to reshape the narrative of the last decade, including the president’s challenges to the 2020 election results.

However, the reconciliation remains precarious. Mr. Cohen has already publicly admitted that he does not agree with the president on all issues, suggesting he may not always adhere to the president’s talking points.

Their two-decade relationship began with real estate disputes rather than politics. After purchasing apartments in two of Mr. Trump’s New York buildings, Mr. Cohen gained the president’s attention during a mid-2000s conflict with the condo board at Trump World Tower.

For Mr. Cohen, who had idolized Mr. Trump since his youth on Long Island, the relationship offered a mentor; for Mr. Trump, Mr. Cohen was an ideal “bulldog” enforcer.

Mr. Cohen fulfilled that role, acting as Mr. Trump’s “designated thug” by threatening adversaries and occasionally managing real estate projects. Though he held no formal role in the 2016 campaign, he remained politically indispensable.

Most notably, Mr. Cohen managed the cover-up of a potential scandal involving porn actress Stormy Daniels, paying her $130,000 to remain silent about a sexual encounter with Mr. Trump.

In 2018, Mr. Cohen pleaded guilty to several federal crimes related to the payoff, maintaining that he acted under Mr. Trump’s direction. He was the only person to serve prison time for the arrangement. After being released during the pandemic, he was briefly re-incarcerated when he refused to sign a non-disclosure agreement regarding a potential book—a move a judge later called “retaliatory.”

Upon his release, Mr. Cohen became a fierce critic, authoring the books “Disloyal” and “Revenge” and launching the “Mea Culpa” podcast. He collaborated extensively with the Manhattan district attorney’s office, which eventually indicted Mr. Trump, and testified in a civil fraud case brought by Ms. James.

Mr. Trump responded by labeling Mr. Cohen a “rat” and a “liar,” even filing a lawsuit that was dropped shortly before the president was scheduled for deposition.

For years, Mr. Cohen remained defiant, boasting of his cooperation with Congress and law enforcement to ensure Mr. Trump was held responsible, even likening the president to a mobster on social media.

Despite his public stance, some associates suggest Mr. Cohen never truly wanted a break from Mr. Trump and would have preferred his former orbit over the accolades of the political left.

Following Mr. Trump’s return to office last year, Mr. Cohen began seeking a way back. This effort culminated in the Bedminster meeting. While Boris Epshteyn, the president’s top legal adviser, was present, it remains unclear who arranged the meeting.

The Bedminster meeting served as an icebreaker. By late summer, Mr. Cohen’s public tone began to soften, culminating in a January Substack essay where he argued that his testimony was involuntary and that prosecutors used “inappropriate leading questions” to steer his answers.

Mr. Cohen claims that the liberal backlash to this essay caught Mr. Trump’s attention. A Trump associate relayed the president’s sympathy, prompting Mr. Cohen to text the president expressing a desire to end their “exhausting feud.” According to Mr. Cohen, this led to a subsequent meeting in Florida about six or seven months ago.

“We rekindled our relationship because of a shared experience of betrayal,” Mr. Cohen explained.

Mr. Cohen also reached out to allies like Lara Trump, who hosted him on her podcast, where he defended Mr. Trump regarding past associations with Jeffrey Epstein.

Ultimately, this path led to his new role at WABC. The station’s owner, John Catsimatidis—a long-time Trump supporter—confirmed he consulted with the White House before hiring Mr. Cohen, though he declined to provide further details.

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