"[13] In his book, Winning Right, Gillespie described himself as someone who "all but had 'Democrat' stamped on his birth certificate," but had become increasingly uncomfortable with the leftward tilt of the national party and believed it wasn't taking the threat of Communism seriously.

As he saw it, he and Ireland were classic Reagan Democrats who became Republicans–"a southern conservative and a young northeastern ethnic Catholic who no longer felt comfortable in the party of their heritage.

[16] In 1999, Gillespie worked as the Press Secretary for the Presidential campaign of John Kasich until his withdrawal from the race and endorsement of George W.

[13] In 1997, Gillespie joined the lobbying firm BGR Group (Barbour, Griffith & Rogers), and advised Senate Republicans during the impeachment of Bill Clinton.

[19] The conservative government watchdog Judicial Watch said that Gillespie's ties to corporations may pose a conflict of interest for him as governor, and that this is a "nonpartisan concern".

[19] In 2003, Gillespie was selected as Chairman of the RNC, serving in that role through the 2004 elections that saw President Bush win re-election and Republicans retain control of the House and Senate.

[26] A later Post article described Gillespie's role orchestrating a PR unit dedicated to "selling the surge to American voters and the media.

After Gillespie was announced chairman the RSLC is reported to have laundered $1.5 million from the Poarch Band of Creek Indians to Alabama Speaker Mike Hubbard and a group associated with Jack Abramoff.

[34] In December 2013, Gillespie told Politico that he was considering a first-time political run in 2014 against Mark Warner, a popular Democratic incumbent U.S.

[42][43] According to The New York Times in July 2017, Gillespie "sought to strike a delicate balance when pressed about Mr. Trump, who is highly unpopular here.

He refused to say Mr. Trump's name, but warned that Mr. Northam, a Democrat, risked hurting Virginia's economy—which relies greatly on the federal government—by attacking the president so fiercely.

[47] In August 2017, The Washington Post reported that Gillespie hired Jack Morgan, an operative in the Trump 2016 campaign for president.

[48] Morgan has made controversial statements, such as saying that the country is on the brink of civil war and that communists are behind efforts to remove confederate monuments.

[47] In October 2017, former president Barack Obama took what The Washington Post described as "the unusual step" of criticizing Gillespie over his use of ads on Latino gang violence which he said sowed fear and were "as cynical as politics gets".

[49] After the Unite the Right rally in Charlottesville, Gillespie condemned the far-right protestors, saying, "[We] reject the people who came in, largely from outside our Commonwealth, and brought their hate, their white supremacism, their neo-Nazism with them.

"[50] After Donald Trump's controversial comment that there were "fine people on both sides," Gillespie said there was "no moral comparison between white supremacists and 'those that show up to condemn them for espousing that kind of hate-filled speech.

'[50] Gillespie criticized Northam for casting the deciding "no" vote to stop a Republican bill which would have banned sanctuary cities in Virginia.

During the campaign, Gillespie and Trump accused Northam of being responsible for the increased activities of the MS-13 gangs and of being "in favor of sanctuary cities that let dangerous illegal immigrants back on the streets"[51][52] and that this contributed to the surge in MS-13 violence; a notion that FactCheck.org found to be "misleading".

[55] In October, the Latino Victory Fund, which supported Northam, released an ad in which a pickup truck, adorned with a Gillespie bumper sticker, a "Don't tread on me" license plate, and a Confederate flag, chases down minority children and corners them in an alley—one of the children in the ad then wakes up, revealing the scene to have been a nightmare.

"[58] The ad was pulled the following day in the hours after a terrorist attack in New York City, in which a man killed several people by running them over with a truck.

"[58] FOX 5 DC reported that the Northam campaign had accepted $62,000 as an in-kind media contribution from the Latino Victory Fund.

[65] Gillespie said he would support a ban on late-term abortions after 20 weeks in Virginia, with exceptions for cases of rape, incest, or pregnancies that endanger the life of the mother.

Gillespie at first dodged the question but when pressed again, answered, "I believe there is ample scientific evidence that contributes to climate change but I'm not entirely dismissive of those who have a different point of view.

"[73] In September 2017 Gillespie supported President Trump's decision to withdraw the United States from the Paris Climate Agreement.

[77] In response to criticism of his lobbying history, Gillespie's campaign said he and his wife would place their assets in a blind trust and that he would be "an honest, ethical, principled, hard-working, faithful servant-leader worthy of Virginia.

[68][79] In 2014, Gillespie said that he was opposed to the 2010 Affordable Care Act (commonly called Obamacare), criticizing it for its "negative impacts" and stating that he would "repeal and replace it.

[68] In July and August 2017, Gillespie said that he opposes "sanctuary cities", which adopt policies designed to not prosecute people solely for being undocumented.

[86] In September 2017 he said he would oppose any legislation that would dictate which bathrooms that transgender individuals could use, such as the controversial North Carolina Public Facilities Privacy & Security Act.

[87] Earlier, in January 2017, Gillespie did not take a firm position when the Virginia General Assembly was considering a bathroom bill, opting instead to criticize the Obama administration for mandating that public schools allow transgender students to use the restrooms of their choice while saying that localities should decide on the issue.

[90][91] In the final weeks of the 2017 gubernatorial campaign, Gillespie began running an ad criticizing Democrats for restoring voting rights to more than 200,000 felons, including John Bowen, whose rights were restored based on his completing sentence for an earlier conviction while he was awaiting trial on a new charge of possessing one of the largest child pornography collections in Virginia's history.