[10] As manager of Bloomberg's 2005 re-election campaign, Sheekey was given 'free rein' to build a coalition of support for the mayor that included "unions, Democratic officials and liberal activists like NARAL Pro-Choice New York.

Following re-election in November 2005, Bloomberg had "declared war on the National Rifle Association, come out publicly against key elements of the plan for ground zero [the original World Trade Center site] of his fellow Republican, Gov.

George E. Pataki, and, through intermediaries, threatened to help Democrats take control of the State Senate from his fellow Republicans if they do not provide more money for city schools."

[15] Sheekey played a prominent role in developing projects such as PlaNYC and obtaining billions in school construction funds for New York City from state legislators.

[19] Sheekey serves on the board of the ONE Campaign, alongside the likes of U2's lead singer Bono, Sheryl Sandberg, John Doerr, Lawrence Summers, and Susan Buffett.

Tech:NYC is a non profit organization that represents the interest of New York City's technology sector through the support of member companies like Google, Bloomberg L.P., Uber, and Facebook.

[26] Bloomberg formally announced he would not run on March 7, 2016, stating that there was too high of a risk his candidacy could lead to the election of Donald Trump or Senator Ted Cruz.

In 2017, Sheekey proposed that Bloomberg Philanthropies cover the gap created when Donald Trump withdrew the U.S. from the Paris climate accords.

[34] Sheekey had previously said that Bloomberg would have an advantage as a candidate — and would work to ensure any Democratic nominee would defeat the incumbent — because of his business acumen and technological knowledge.

"[35] Sheekey discussed the reasoning behind entering the race in a December 2019 interview with David Plouffe, who ran President Obama's 2008 campaign.

Thank you, Kevin, for the ways in which you promote Franco-American friendship and collaboration, notably for your dedication to the causes of climate, health and the fight against inequalities" (Tweet) – via Twitter.

Sheekey's political philosophy is compared to the military doctrine of former U.S. Secretary of State Colin Powell: "Use overwhelming force.