Twenty-second Amendment to the United States Constitution
As worded, the primary focus of the 22nd Amendment is on limiting individuals twice elected to the presidency from being elected again. Due to this, several issues could be raised regarding the amendment's meaning and application, especially in relation to the 12th Amendment, ratified in 1804, which states, "But no person constitutionally ineligible to the office of President shall be eligible to that of Vice-President of the United States". While it is clear that under the 12th Amendment the original constitutional qualifications of age, citizenship, and residency apply to both the president and vice president, it is unclear whether someone who is ineligible to be elected president could be elected vice president. Because of this apparent ambiguity, there may be a loophole in the 22nd Amendment whereby a two-term former-president could be elected vice president and then succeed to the presidency as a result of the incumbent's death, resignation, or removal from office (or even succeed to the presidency from some other stated office in the presidential line of succession).
2000 United States Senate election in New York
Giuliani and Clinton got another chance to battle each other during the 2016 U.S. presidential election, when she was the Democratic nominee and he was one of the few high-profile Republicans to enthusiastically campaign for that party's nominee, Donald Trump. As the "Washington Post" wrote, "Rudy Giuliani is finally running the race against Hillary Clinton that he first contemplated some 17 years ago: a brutish bout under a white-hot spotlight." His actions on behalf of Trump included not only fiery attacks on Clinton's record as Secretary of State but also charges that she was experiencing significant problems with her health. A Clinton spokesperson responded by pointing out that it was Giuliani who had left the 2000 senatorial race in part for health reasons, not Clinton. Giuliani said Clinton was "too stupid to be president" for having stayed married to her husband following the Lewinsky scandal. Clinton sent some mild barbs Giuliani's way during the Alfred E. Smith Memorial Foundation Dinner in October 2016, to which Giuliani responded to with stone-faced silence rather than the usual playing-along mirth. The former mayor also issued a false charge against Clinton's statements regarding her role following the September 11 attacks that he had to apologize for. And in the days leading up to the election, Giuliani implied, and then denied, that he had had inside knowledge of the FBI's late-in-the-campaign reopening of its investigation into the Clinton emails matter. Following Clinton's loss, Giuliani was considered to be on Trump's short list for both Attorney General – if picked, he said he would be open to prosecuting Clinton – and Clinton's past job of Secretary of State – where his potential conflicts from his post-mayoral consulting work, advisor roles, and paid speeches for foreign clients and corporations could have exposed him to some of the same charges that he had made against Clinton when she had held that position. In the event, he was not selected for either position.