Representing Trump: A rotating cast of counselors

From a 1973 encounter with the Department of Justice over his claims of housing discrimination to the recent battles over Trump University and alleged efforts by his attorney to silence a porn star, President Donald Trump is no stranger to the American legal system.

Now, the newest additions to Trump’s legal team may not be a done deal, with Trump’s lawyers citing “ongoing process of conflict review” referring to other clients Joe diGenova and his wife, Victoria Toensing have had or currently represent.

Trump, his companies and members of his family have been involved in thousands of lawsuits over decades and he has personally given dozens of depositions. His history of unorthodox legal strategies and friction with his some of his own lawyers offer clues about his chaotic effort to fend off Special Counsel Robert Mueller’s investigation into possible ties between the Trump campaign and Russia.

In less than one year, he has faced two shake-ups of the legal team defending him in the special counsel’s probe. Trump’s longtime personal attorney Marc Kasowitz, whom he had retained as his lead lawyer to represent him in all matters related to the Russia investigation, was pushed from that role. While he remains on the legal team; he is no longer the lead lawyer.

Kasowitz was replaced by John Dowd, who abruptly resigned on Thursday.

And last week Trump retained diGenova, famous for his fierce defenses of the president on cable television and his insistence that Obama-loyalist factions within the FBI and DOJ are biased against the president. DiGenova and Toensing are veterans in the Washington legal scene.

Sources close to Dowd tell ABC News that he resigned in large part because President Trump was increasingly ignoring his legal advice over the last several months. There’s also growing friction with White House counsel Ty Cobb. Trump has discussed with the closest advisers potentially firing Cobb, the White House lawyer responsible for Russia matters, but has privately assured him his job is safe, sources say.

While some of Trump’s past lawyers have described their client as compliant and easy to work with, sources close to those currently representing the president have described a compulsive side of him that at times can be difficult to manage, say sources with direct knowledge.

Jay Goldberg, who represented Trump personally from 1990 to 2005, recalled to ABC News a client who was at the time “very easy to control” and “very careful in his answers and followed direction all the time.” He insisted Trump is a very different client than how he appears on television.

“People think he shoots from the hip and sometimes he is too lippy,” Goldberg said of the president. “But behind it is a very organized person who knows what he’s doing.”

Michael Wildes, the managing partner at Wildes & Weinberg PC, represented the Trump Organization on immigration matters for more than a decade, as well as Trump Models, the Miss Universe Organization and Melania Trump and her family. He told ABC News that “as a proud Democrat” he profoundly disagrees with Trump on policy matters, but his experience representing him was generally positive.

Trump has the ability to “aptly cut through legal issues, to break things down to rudimentary elements, in matters that often got complicated. And he has a quick wit to boot,” Wildes said. “The people I dealt with in his inner circle were all highly talented, responsible and professional,” Wildes said about his working relationships that predate Trump’s presidency.

There’s no question Trump is a demanding client, who expects only the best results from his lawyers.

Goldberg recalls the often-used phrase from Trump: “Don’t tell me that it can’t be done,” Trump would say. “Your job is to tell me how it can be done. You get it?”

Legal experts have been alarmed by what they consider questionable behavior in connection with some of the cases he has faced such as when he repeatedly blasted Judge Gonzalo Curiel, who presided over a case against the now-defunct Trump University.

“Everybody says it, but I have a judge who is a hater of Donald Trump, a hater. He’s a hater. His name is Gonzalo Curiel and he is not doing the right thing,” Trump said at a 2016 campaign rally. “So what happens is, the judge, who happens to be, we believe, Mexican, which is great; I think that’s fine. You know what? I think the Mexicans are going to end up loving Donald trump when I give all these jobs, OK? I think Judge Curiel should be ashamed of himself.”

And his lawyers are facing a range of legal challenges with a client who makes no secrets of how he wishes to handle them.

He’s given contradictory messages about the standing of those currently representing him, tweeting just days ago that reporting he was going to add another lawyer to his legal team was “wrong” insisting he is “VERY happy with my lawyers, John Dowd, Ty Cobb and Jay Sekulow.”

Since that tweet just twelve days ago, Dowd has resigned and Trump hired diGenova.

He tweets frequently about the special counsel probe, even as his lawyers and close advisers have strongly advised against it. That came to a head this week when Trump for the first time called out Robert Mueller by name — attacking his investigation and the political leanings of the team he has assembled.

According to sources Dowd had been at odds with Trump for months over the whether President Trump would meet with members of Mueller’s team for an interview and had advised the president against it. Immediately following Dowd’s resignation on Thursday, Trump declared: “I would like to. I would like to,” when asked if he would like to answer questions from the special counsel.

Goldberg — who believes the ongoing investigations into the Trump campaign's possible contacts with Russia should end — says he still speaks to the president regularly.

He says he received a phone call from the president a recent Saturday morning and advised the president that it would be a mistake to sit for an interview with the special counsel.

Advisers also fear the president could contradict himself during a potential wide-ranging interview with Mueller, sources have told ABC News.

With John Dowd gone, it’s unknown who will take the lead on negotiating a potential interview with Mueller’s team, but one thing is clear — the president says he still wants to speak with him.