I’d call this “too good to check,” but Donald Trump has a long history of complaints from aggrieved contractors and other associates over allegedly unpaid bills. Does that include his most prominent wingman, the attorney Trump personally selected to head his 2020 election challenges? And, not coincidentally, the man who has now become Trump’s co-defendant in a racketeering indictment in Georgia?

So says Trump’s favorite New York Times reporter, Maggie Haberman, who reports along with Ben Protess that Rudy Giuliani has tried for years to collect millions of dollars in owed legal fees. Now that his own legal fees are skyrocketing, Giuliani may go broke unless Trump pays up. More importantly, Giuliani may not have money to defend himself effectively in Georgia without it, the NYT sources suggest:

Still, for the better part of a year, as Mr. Giuliani has racked up the bills battling an array of criminal investigations, private lawsuits and legal disciplinary proceedings stemming from his bid to keep Mr. Trump in office after the 2020 election, his team has repeatedly sought a lifeline from the former president, according to several people close to him. And even as the bills have pushed Mr. Giuliani close to a financial breaking point, the former president has largely demurred, the people said, despite making a vague promise during their dinner at Mar-a-Lago to pay up.

Mr. Giuliani, 79, who was criminally charged alongside Mr. Trump this week in the election conspiracy case in Georgia, is currently sitting on what one person familiar with his financial situation says is nearly $3 million in legal expenses. And that is before accounting for any money that Mr. Giuliani, the former mayor of New York City, might be owed for his work conducted after Election Day on Mr. Trump’s behalf.

Mr. Trump’s political action committee, which has doled out roughly $21 million on legal fees primarily for Mr. Trump but also for a number of people connected to investigations into him, has so far covered only $340,000 for Mr. Giuliani, a payment made in late May.

Why won’t Trump pay his bills? Obviously, his other attorneys (including Michael Cohen!) have asked this, but Giuliani has been an inner-circle figure, one who has put himself and his livelihood at risk to do Trump’s bidding. According to the NYT’s sources — clearly all from Giuliani’s camp — Trump is sore that Giuliani didn’t deliver the presidency:

Over a nearly two-hour dinner, Mr. Costello pressed Mr. Trump to cover not only Mr. Giuliani’s legal bills, but also to pay him for the work Mr. Giuliani provided Mr. Trump in the wake of the 2020 election.

Mr. Trump resisted, noting that Mr. Giuliani did not win any of those cases. Mr. Costello, who did most of the talking for Mr. Giuliani, said that the money was not coming out of Mr. Trump’s own pocket, but rather the coffers of his PAC. By the end of the dinner, Mr. Trump agreed that Mr. Giuliani would be paid, one person said. But in the weeks that followed, neither he nor the PAC delivered. And Mr. Giuliani was growing more and more desperate.

Is this true? It certainly sounds like the authentic Trump, but don’t forget that we’re only getting one side of the story here, too. Even so, one has to imagine that attorneys that choose to represent Trump now and in the future will require large retainers and up-to-date payments as a condition of business.

Put aside the what of this report, for now, and consider the why. Why has Giuliani’s camp gone to the New York Times with this issue now? The timing of this leak, coming just a couple of days after the Fulton County indictment of Trump, Giuliani, and 17 others, cannot be coincidental.

The most immediate reason is the Fani Willis indictment that names Giuliani for the first time in a criminal indictment for the work he did for Trump. Giuliani considers it nonsense, and he may well be right, but it’s going to be very expensive nonsense for Giuliani and the other defendants. If Giuliani can’t get the back pay he’s owed, he won’t be able to properly defend himself against the racketeering charges. That has to be a clear motivation for Giuliani to go public as a means to shame Trump into paying his bills.

Of course, Trump has demonstrated an almost unique immunity to shame in his decades on the public stage. Giuliani knows this, too. So what other reason might there be to go public, other than sheer desperation? Might this be an attempt by Giuliani’s friends to remind Trump of just how much Giuliani knows about what happened inside “Stop the Steal” and of Trump’s state of mind during the election challenges? If Willis and/or Jack Smith could flip Giuliani, imagine what that might do for their prosecution of Trump and others in his orbit.

Haberman and Protess include a curious declaration from their sources on this point:

But people close to both Mr. Trump and Mr. Giuliani take it as an article of faith that the former mayor would never cooperate with investigators in any meaningful way against the former president.

Never? Is Trump sure about that? The mere mention of this suggests that the thought has crossed some of the minds close to Giuliani. Stiffing someone of millions of dollars after years of faithful and unpleasant service is a betrayal that may impact that “faith” in unexpected ways. Giuliani is on his way to being disbarred anyway, so at some point he might get past the attorney-client privilege issue if the client won’t pay the attorney for the privilege. Especially if he’s looking at both financial ruin and a potential prison term without the resources to fight Fani Willis effectively.

Perhaps Giuliani’s circle didn’t intend this as a nice business ya got there message, but that is what this looks like. And it might start looking like that to Trump, or at least the people around Trump, and that might get a check in the mail to Giuliani.