In 1996, he moved to Chicago to work for a real estate investment trust, General Growth Properties, where he eventually became senior vice president for marketing and communications.

[3] President Obama nominated Brewster for the post of Ambassador to the Dominican Republic on June 21, 2013,[5] to replace Raul Humberto Yzaguirre, who resigned in May citing health reasons.

[9][10] On the evening of that day, Brewster married his partner of 25 years, luxury real estate executive, author and social activist, Bob J. Satawake.

During a July 2013 press conference, Cardinal Jesús López, referred to Brewster as a maricón, equivalent to "faggot" in American English.

"[15] On November 25, 2015, speaking during a Thanksgiving Day luncheon at the American Chamber of Commerce in the Dominican Republic, Brewster discussed joint efforts at improving education and public safety and in supporting investments in small business.

In words that do not appear in the transcript of the remarks, he was quoted as inviting his critics to match their rhetoric by cutting off their own ties to the U.S., saying they could "go to the [U.S.] embassy and turn in their visas".

[20] After the announcement, USAID director Alexandria L. Panehal appeared to reference LGBT candidates for public office when discussing her agency's grants.

The petition asked President Obama to remove Brewster as ambassador "for primarily promoting in his official duties an LGBT agenda inconsistent with the Christian cultural values and tradition of the Dominican Republic."

Ambassador Susan Rice commented: "He has the full support of this President, this White House and the entire U.S. government and I know he will continue to advocate tirelessly for the interests of the United States in the Dominican Republic.

[14] A lawsuit seeking a court order to prevent Brewster and other embassy staff from visiting schools along with the ambassador's husband was dismissed on 5 April 2016.

[26] In late April, Auxiliary Bishop Victor Masalles said that Brewster's support of LGBT rights in the DR was an instance of "ideological colonization", a term used by Pope Francis, and that he suspected the U.S. government was pressuring Santo Domingo to modify its constitution.

He said Brewster showed "an inability to distinguish his activism with his role as an ambassador" and that: "...we're suffering [from] him as a nation, as a culture, as a country that has its own uses and customs, and its own laws.

Among them, to quash the efforts that we as Dominican LGBT civil society activists have undertaken to defend ourselves against the hateful, violent and stigmatizing discourse orchestrated by hierarchies within the Catholic and Evangelical churches and the conservative individuals who support them.For his work against corruption and defending Human Rights, Ambassador Brewster received numerous awards including 2016 Foreign Policy Magazines 100 Global Thinkers, 2016 OUT 100 and finalist for the Susan Cobb Award presented to top diplomats by the US State Department.