Team of Vipers: My 500 Extraordinary Days in the Trump White House is a book-length memoir written by former Trump administration Special Assistant to the President and Director of Message Strategy[1] Cliff Sims who had previously operated the conservative Alabama news site Yellowhammer News.

[6] On January 29, 2019, President Donald Trump tweeted that the book is "boring" and "fiction" and that Sims was a "low level staffer" who "pretended to be an insider when in fact he was nothing more than a gofer".

Sims contends his book contained only information he gained as an employee of the federal government and hence any nondisclosure agreement is unenforceable and violates his First Amendment rights.

[11] After a short legal dispute, Trump realized that the book actually put him in a positive light while criticizing senior staff.

[12] In August 2020, it was reported by several outlets[13] that Sims was once again working for the Trump administration, performing speech writing duties for the 2020 Republican National Convention.