One reason is he doesn't always pay his bills (another trait his base endorses). Another reason is he isn't a good client, he can't keep his mouth shut.
Everyone knows most criminals talk their way into jail.
George Conway: Why Trump had to hire this legal odd couple
"This is what happens when you don’t pay your legal bills.
President Trump, whose businesses and now campaign have left a long trail of unpaid bills behind them, has never discriminated when it comes to stiffing people who work for him. That includes lawyers — which is part of the reason he found the need to make some curious last-minute tweaks to his team, announcing the addition of the legal odd couple of Alan Dershowitz and Kenneth W. Starr.
The president has consistently encountered difficulty in hiring good lawyers to defend him. In 2017, after Robert S. Mueller III became special counsel, Trump couldn’t find a high-end law firm that would take him as a client. His reputation for nonpayment preceded him: One major Manhattan firm I know had once been forced to eat bills for millions in bond work it once did for Trump. No doubt other members of the legal community knew of other examples.
Of course, being cheap wasn’t the only reason Trump struck out among the nation’s legal elite. There was the fact that he would be an erratic client who’d never take reasonable direction — direction as in shut up and stop tweeting. Firms also understood that taking on Trump would kill their recruiting efforts: Top law students of varying political stripes who might be willing, even eager, to join a firm that provides pro bono representation to murderers on death row, want nothing to do with Trump.
That left Trump to be personally defended in the Mueller investigation by a random patchwork of counsel, including Jay Sekulow, a lawyer specializing in religious liberty cases, and John Dowd, a Washington solo practitioner who, according to Bob Woodward, viewed Trump as a “f---ing liar.” (Dowd denies that.) Last but not least, Trump had the assistance of Rudolph W. Giuliani — who has done more than anyone other than Trump himself to get Trump impeached.
Contrast that unimpressive crew with the team assembled by President Bill Clinton, who had not one, but two, top-notch law firms defending him: global powerhouse Skadden Arps, with heavy-hitterBob Bennett, to handle the Paula Jones case; and the elite Washington defense firm, Williams & Connolly, led by the brilliant David Kendall, to handle the Whitewater investigation, its Monica Lewinsky spinoff and impeachment.
Precisely because he never had a defense team truly suited for the task at hand, Trump found the need now to add to the mix. But the mix still makes no sense. On the team, as of Friday, are the legal odd couple of Harvard Law School professor emeritus Dershowitz and former federal appeals court judge Starr.
It’s hard to see how either could help.
Dershowitz may be a genius in some ways, but he’s not necessarily the advocate you want on your side. Judges have told me they find him condescending in manner and tone — not the approach you want before a court consisting of 100 U.S. senators. And he’s wont to make off-the-wall arguments. As his former Harvard colleague Professor Laurence Tribe has put it, Dershowitz “revels in taking positions that ultimately are not just controversial but pretty close to indefensible.” Dershowitz’s recent assertion that the Supreme Court could order the Senate not to conduct an impeachment trial illustrates the point. Not only is that claim indefensible— it’s also ridiculous.
And then there’s Starr. I know and like Starr, but I can’t comprehend what he’s doing here. He’s best known as the independent counsel whose investigation led to the impeachment of Clinton. That’s hardly helpful for Trump, because Clinton was a piker compared with Trump.
Clinton’s core offense was to obstruct a private civil action about pre-presidential conduct and cover up sexual misconduct — none of which had involved abuse of presidential power. From a constitutional standpoint, that’s a trifle compared with extorting a foreign nation by cutting off federal military funds in an effort to interfere with an upcoming U.S. presidential election.
As if that were not enough, in the Clinton case, Starr argued that Clinton had committed an impeachable offense by blocking witness testimony and documents. Oops.
Any litigator will tell you that adding to your legal team on the eve of trial most likely will not produce better lawyering but, rather, chaos. In that sense, at least, Trump will be getting the representation he deserves."
https://www.washingtonpost.com/opini...rr-dershowitz/
A billionaire who doesn't pay his bills. There's a good indication of character that trumpys admire.
They must. They defend everything he does.