How unusual is Rudy Giuliani's involvement in government?

Question

Recently Rudy Giuliani's name has been all over the news, and my understanding is that he has been deeply involved in negotiating US foreign policy in Ukraine. From Wikipedia's article on the Trump–Ukraine scandal:

Since at least May 2019, Giuliani has been pushing for Volodymyr Zelensky, the newly elected president of Ukraine, to investigate Burisma, as well as to check if there were any irregularities in the Ukrainian investigation of Paul Manafort.

[...]

As early as May 2019, Trump had instructed State Department officials attempting to set up a meeting with Zelensky to work with Giuliani. Establishing Giuliani as a gatekeeper in this fashion circumvented official channels.

How common is it for the president's lawyer to take such an active role in official government business?

Answer 1

Short answer? Very uncommon.

Official government business tends to be performed by government officials.
Rudy Giuliani does not hold an official cabinet position in the way that, to give a random example, an Attorney General would.
There is no apparent reason that the role Giuliani is playing couldn't be covered by an established position.

Official overseas negotiations are performed by appointed diplomats and ambassadors. Almost every country has at least one US embassy or consulate, including Ukraine (list of US embassies).

National legal matters are covered by the lawyers of the federal government (headed by the attorney general).

Legal issues concerning the administration are usually taken care of by the White House Counsel, a presidentially appointed position.

Personal lawyers to a president, like Giuliana, are normally only involved in matters that involve the president as a person and there is no historical precedent that I could find of anything close to this level of policy involvement.

Answer 2

Rudy Giuliani is a first.

As a little history, US security clearances began in 1939 via the Hatch Act, which required that government employees not be a member of organizations that desired to overthrow the US government.

There have been no non-cleared, non-elected people since 1939 that have served in such an important role as Giuliani. Even those that served before 1939 were thoroughly vetted by the military or Congress, and the vast majority had been specifically confirmed as a cabinet post by Congress.

As central policy-making by the White House carries security issues with it, all those who negotiate on behalf of the US government must be cleared to deal with the secrets, tactics, and desired results that such a role would naturally require.

As one cannot adequately prove a negative, I will disprove several other offered examples.

1. Wild Bill Donovan had major military posts, was the assistant Attorney General of the United States to Harlan Stone, then John Sargent, serving in the antitrust division of the DOJ. This is a man with the highest of security clearances when he was an adviser to FDR.
2. Vernon Walters served as official interpreter for Truman, receiving a very high security clearance to do so, as he was having to translate detailed treaty language. When he smuggled Kissinger in and out of North Vietnam, he was doing so as a military attache, utilizing his high military rank as security clearance for his diplomatic work. Later, Congress confirmed Nixon's appointment of him as Deputy Director of the CIA, which obviously is well beyond any need to justify clearance-wise.
3. James Monroe was a founding father, involved in high levels of both state government, a position as a Senator, and a Senate-confirmed minister (diplomat) to France before he assisted Livingston in the Louisiana Purchase. While there were no security clearances back then, he was approved by Congress as a lawful official of the US government.
4. Sidney Blumenthal was a senior adviser to Bill Clinton, and thus had to receive Top Secret security clearance to do so. He left government in 2001 in disgrace, and has not served in any sort of ambassadorship or diplomatic role since that point. As a member of the Clinton Foundation in 2011, he sent one-way memos (that turned out to be extremely bad intel) about Libyan president Gaddafi to Hillary Clinton, but there was no evidence that Clinton provided him with intelligence or gave him responsibility for negotiation of anything.

These were all men who had either undergone strict security checks via the US military or the US government for their roles long before they were asked to serve their country in less-formal settings. Rudy Giuliani has absolutely no security clearances, nor has he ever at any point in his life, even immediately following 9/11.

Answer 3

Nothing in the Constitution, law, or precedent obliges any president regarding any channel whatsoever through which to carry on foreign affairs, and not surprisingly presidents have utilized this blanket authority to carry out foreign affairs in a manner of their choosing. There is certainly some precedence for use of "special or personal envoys", "roving ambassadors" and the like, which Rudy Giuliani could so be considered. There are no requirements, Constitutional or otherwise, for these roles, and serve as trusted advisers to the President in sensitive matters. For example, FDR relied heavily on Wild Bill Donovan in much the same way as Trump does Giuliani.

Also Vernon Waters served in a similar capacity over a few administrations, but most notably as a roving diplomat for Reagan. Later Waters became a formal ambassador in several capacities.

This practice most likely started when James Monroe assisted the U.S. French ambassador Robert R. Livingston to negotiate the Louisiana Purchase in Paris, representing President Thomas Jefferson. While Monroe was an ambassador to France previously under Washington, he was actually just assisting Livingston, but played the more commanding role. Jefferson also sent Monroe to negotiate west Florida with Spain.

Do not confuse Ambassadors-at-large, with roving ambassadors or personal envoys. They are commissioned officers of the United States as defined under Article 2. However there is some conflation of the term with "roving" ambassador.