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In light of President Trump's allegations against the Obama administration: Is it legal for the President of the United States to order a wiretap and/or other federal surveillance of a citizen of the United States?

Are there any qualifications needed to be met in order to request such surveillance?

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"Any federal surveillance" is too broad to address (it could involve agents watching a person while at Starbucks, which is currently legal), but the question of wiretapping can be answered with reference to specific law. 18 USC 2511 is the federal wiretapping statute, which generally outlaws "wiretapping" – i.e., recording a conversation where neither party consents to the recording. (If at least one party consents, it is allowed, though some states require all parties to consent.) There are a number of special cases, starting in subsection (2), where party consent is not required. Court orders would be one of those conditions. Another is if the Attorney General certifies in writing that the tap is legal and necessary to catch a spy. (2)(e) says, in particular:

it shall not be unlawful for an officer, employee, or agent of the United States in the normal course of his official duty to conduct electronic surveillance, as defined in section 101 of the Foreign Intelligence Surveillance Act of 1978, as authorized by that Act.

where electronic surveillance is defined (partially) as

the acquisition by an electronic, mechanical, or other surveillance device of the contents of any wire or radio communication sent by or intended to be received by a particular, known United States person who is in the United States, if the contents are acquired by intentionally targeting that United States person, under circumstances in which a person has a reasonable expectation of privacy and a warrant would be required for law enforcement purposes

This seems to satisfy the circumstances described in the question – the act would be "electronic surveillance" as defined in that section of the law. But the wiretap law also says "as authorized by that Act", so now we have to turn to authorization (without court order). 50 USC 1802 says

Notwithstanding any other law, the President, through the Attorney General, may authorize electronic surveillance without a court order under this subchapter to acquire foreign intelligence information for periods of up to one year if the Attorney General certifies in writing under oath that...

There are three conditions that have to be met. The second, (B), is that

there is no substantial likelihood that the surveillance will acquire the contents of any communication to which a United States person is a party

which would rule out the use against US persons asked about. Condition (A) likewise limits surveillance to

the acquisition of the contents of communications transmitted by means of communications used exclusively between or among foreign powers

So wiretapping without a court order is not authorized against a US person (which includes US citizens plus numerous other non-citizens with a "connection" to the US, including and not limited to permanent residents).

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