[1] A graduate of Evanston Township High School (1975) and Stanford University (1980), he served on the White House staff under both Ronald Reagan and George H. W. Bush and on each of their presidential campaigns from 1980 to 1992.

In the past, he was a senior fellow at both the Free Enterprise Fund and the New America Foundation, a lecturer at the Graduate School of Political Management at The George Washington University, a member of the Board of Advisors at the National Federation of Republican Assemblies, and a contributing editor of The American Conservative and USA Today.

In 2011, he became the co-chair of the RATE Coalition, a bi-partisan group of 35 companies and associations dedicated to corporate tax reform.

[3] Although he is a Republican with views broadly in sync with the GOP, he has sometimes divergent ideas: For example, in a Bloggingheads discussion with economist Glenn Loury, Pinkerton described his political ideology as "Hamiltonian".

[5] Leaked emails obtained by Buzzfeed News showed that former Donald Trump Campaign Manager and then Breitbart Executive Chairman, Steve Bannon, sent Pinkerton an article due to be published on far-right website on the taxonomy of the alt-right.