Roosevelt relied heavily on his advisor "Wild Bill" Donovan in much the same way as Trump does on Rudy Giuliani. Both were personal envoys. And Vernon Waters served as a roving diplomat for Reagan. None of these are official Article 2 officers, but are they considered then White House staff and paid from that budget, or other taxpayer provided budget, for the work they are doing on behalf of the president that would be considered public?

I wouldn't expect Giuliani to be paid for the work he is doing as the President's lawyer to be considered part of that. So just the public work please.

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    This question was inspired by @phoog 's points on a related question. – K Dog Nov 4 at 19:05
  • I don't know about pay, but Donovan and Roosevelt were from different political parties (Donovan was Republican), although both were what today would be called "war hawks". Different times. Also the US had basically no intelligence agency at the time of Donovan's trip to the UK. Roosevelt would create the OSS and appoint Donovat to lead it a bit thereafter. – Fizz Nov 4 at 19:41
  • And a lesser known fact is that Donovan had personal business connections with Churchill before the war nps.gov/articles/… – Fizz Nov 4 at 19:55
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    And Churchill sent William Stephenson to the US, who again apparently had no official function at the time (and over the objections of UK intelligence chief Menzies). Stephenson had worked as Churchill's personal spy on German rearmament in the interwar period. – Fizz Nov 4 at 20:16
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    There was a entire group of Wall Street lawyers, accounts, etc that worked for a $1 a year for the US Government. Wild Bill was a Medal of Honor recipient who also a lawyer who headed the OSS which was the predecessor to the CIA. – GB - AE7OO Nov 5 at 1:42

Partial answer for Rudy Guiliani, he claims his work for Donald Trump is pro bono and nobody is paying him.
This includes travel arrangements to Ukraine for the in-person talks:

In an interview with The Daily Beast this week, Giuliani steadfastly denied that he was paid for any work he did in Ukraine, saying that he helped Trump on a “pro bono” basis. He said that the costs of his travel were covered by private clients for separate work that happened to correspond with his Ukraine portfolio.
-- Dems Want to Know: Who Paid Rudy - The Daily Beast (2019-10-11)

Another publication trying to dig into his financial situation is the Washington Post, with articles like:
We have no idea who is paying Rudy Giuliani (2019-10-10)

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    Happy to be the accepted answer, but if anybody feels like adding more detail about Donovan and Waters it could make for a more comprehensive picture. – Mara Nov 5 at 11:21

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