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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. – user9790 Nov 4 '19 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 '19 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 '19 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 '19 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 '19 at 1:42
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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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Another partial answer based on Kurt Volker, who is the United States Special Representative for Ukraine Negotiations. While not serving under the president, he serves under the Secretary of State.

The Wikipedia article on United States Special Envoys characterizes these positions in general as:

Special Envoys, Representatives, Coordinators, and Advisors representing the federal government of the United States. These officials typically report directly to the United States Secretary of State. They normally require confirmation by the U.S. Senate. In some cases, when the incumbents have received earlier Senate confirmation to serve as an ambassador, that is not done. This can be particularly important when assigning an official to deal with a breaking crisis or conflict. In contrast to ambassadors who are responsible for the U.S.'s bilateral relations, many envoys oversee a portfolio that cover a broader goal or issue.

In his testimony before Congress on November 20th, 2019, he testified, according to a transcription by rev.com (emphasis mine):

Kurt Volker: (21:45) My last three positions before leaving the senior foreign service in 2009 were as director for NATO in West European affairs at the National Security Council, principal deputy assistant secretary of state for European affairs at the state department, and finally, as US ambassador to NATO. In the spring of 2017 then secretary of state, Tillerson, asked if I would come back to government service as US Special Representative for Ukraine negotiations. I did this on a part-time, voluntary basis with no salary paid by the US taxpayer simply because I believed it was important to serve our country in this way. I believed I could steer US policy in the right direction. For over two years as US Special Representative for Ukraine negotiations, my singular focus was advancing the foreign policy and national security interests of the United States.

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