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Phillips was present in 1960 at the age of nineteen at the launching by [[William F. Buckley, Jr.]] of the group, [[Young Americans for Freedom]],  which drafted the "Sharon Statement" of unyielding conservative principles in Sharon,  [[Connecticut]]. In 1968, he managed the successful senatorial campaign of Moderate Republican [[Richard Schweiker]] in [[Pennsylvania]], later a member of the Reagan [[Cabinet]]. After working in nearly all facets for the Republican Party, Phillips switched to the Democrat label in 1974 and that same year established the nonpartisan grass-roots public policy organization, the Conservative Caucus, which he chaired from its inception until 2011. The caucus opposed the transfer of the [[Panama Canal]] to the Republic of Panama, a measure pushed to passage by U.S. President [[Jimmy Carter]]. It also fought the [[SALT II]] treaty with [[Leonid Brezhnev]], leader of the Soviet Union, which it claimed would weaken American defenses in the [[Cold War]]. The caucus supported [[Ronald Reagan]]'s [[Strategic Defense Initiative]] and the tax reductions of the 1980s.  In 1978, Phillips ran as an unsuccessful Democratic [[primary]] candidate for the [[United States Senate]] seat held by the Moderate Republican [[Edward Brooke]], the first [[African-American]] in the body since [[Reconstruction]], who supported the Great Society. Brooke was renominated but then unseated by the Democrat [[liberal]] Paul Tsongas, who later attracted national attention as an unsuccessful challenger to [[Bill Clinton]] in the 1992 Democratic presidential primaries.<ref name=nyt/>​

Phillips was present in 1960 at the age of nineteen at the launching by [[William F. Buckley, Jr.]] of the group, [[Young Americans for Freedom]],  which drafted the "Sharon Statement" of unyielding conservative principles in Sharon,  [[Connecticut]]. In 1968, he managed the successful senatorial campaign of Moderate Republican [[Richard Schweiker]] in [[Pennsylvania]], later a member of the Reagan [[Cabinet]]. After working in nearly all facets for the Republican Party, Phillips switched to the Democrat label in 1974 and that same year established the nonpartisan grass-roots public policy organization, the Conservative Caucus, which he chaired from its inception until 2011. The caucus opposed the transfer of the [[Panama Canal]] to the Republic of Panama, a measure pushed to passage by U.S. President [[Jimmy Carter]]. It also fought the [[SALT II]] treaty with [[Leonid Brezhnev]], leader of the Soviet Union, which it claimed would weaken American defenses in the [[Cold War]]. The caucus supported [[Ronald Reagan]]'s [[Strategic Defense Initiative]] and the tax reductions of the 1980s.  In 1978, Phillips ran as an unsuccessful Democratic [[primary]] candidate for the [[United States Senate]] seat held by the Moderate Republican [[Edward Brooke]], the first [[African-American]] in the body since [[Reconstruction]], who supported the Great Society. Brooke was renominated but then unseated by the Democrat [[liberal]] Paul Tsongas, who later attracted national attention as an unsuccessful challenger to [[Bill Clinton]] in the 1992 Democratic presidential primaries.<ref name=nyt/>​

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In 1982, Phillips and the [[Houston, Texas|Houston]] political activist [[Clymer Wright]]  urged Reagan to dismiss [[James A. Baker, III]], a Houston [[attorney]] and close ally of then Vice President [[George Herbert Walker Bush]]. Reagan rejected the Wright-Phillips request, and in 1985, named Baker as [[United States Secretary of the Treasury]], at Baker's request in a job-swap with then Secretary [[Donald T. Regan]], a former [[Merrill Lynch]] officer who became chief of staff. Reagan also rebuked Phillips and Wright for waging a "campaign of sabotage" against Baker.<ref>{{cite news|url=https://www.nytimes.com/1982/06/05/us/briefing-186924.html|author=Phil Gailey and Warren Weaver, Jr.,|title=Briefing|publisher=''The New York Times''|date=June 5, 1982|accessdate=January 27, 2011}}</ref>​

In 1982, Phillips and the [[Houston, Texas|Houston]] political activist [[Clymer Wright]]  urged Reagan to dismiss [[James A. Baker, III (DOS)]], a Houston [[attorney]] and close ally of then Vice President [[George Herbert Walker Bush]]. Reagan rejected the Wright-Phillips request, and in 1985, named Baker as [[United States Secretary of the Treasury]], at Baker's request in a job-swap with then Secretary [[Donald T. Regan]], a former [[Merrill Lynch]] officer who became chief of staff. Reagan also rebuked Phillips and Wright for waging a "campaign of sabotage" against Baker.<ref>{{cite news|url=https://www.nytimes.com/1982/06/05/us/briefing-186924.html|author=Phil Gailey and Warren Weaver, Jr.,|title=Briefing|publisher=''The New York Times''|date=June 5, 1982|accessdate=January 27, 2011}}</ref>​

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The fight against Baker was not Phillips' first clash with Reagan. The year before in 1981, he and his friend, the Reverend [[Jerry Falwell]] of Lynchburg, Virginia, opposed the fateful nomination of Moderate Republican [[Sandra Day O'Connor]] of [[Arizona] to the [[United States Supreme Court]] in order to fulfill Reagan's campaign promise that he would appoint the first woman to the high court.  According to Phillips, "People say you can't tell how a Supreme Court nominee will turn out once on the bench. I respectfully disagree. In most cases, it's very clear. I opposed the nomination of Sandra Day O'Connor because it was very clear that she had a pro-[[abortion]] record in the Arizona State Senate and as a state court judge. She was also allied with [[Planned Parenthood]]."<ref name=dflynn>{{cite web|url=https://web.archive.org/web/20120103215640/http://www.flynnfiles.com/blog/phillips/phillips1.htm|title=Interview with Howard Phillips|author=Daniel J. Flynn|publisher=Flynnfiles.com|date=January 3, 2012|accessdate=April 22, 2013}}</ref>

The fight against Baker was not Phillips' first clash with Reagan. The year before in 1981, he and his friend, the Reverend [[Jerry Falwell]] of Lynchburg, Virginia, opposed the fateful nomination of Moderate Republican [[Sandra Day O'Connor]] of [[Arizona] to the [[United States Supreme Court]] in order to fulfill Reagan's campaign promise that he would appoint the first woman to the high court.  According to Phillips, "People say you can't tell how a Supreme Court nominee will turn out once on the bench. I respectfully disagree. In most cases, it's very clear. I opposed the nomination of Sandra Day O'Connor because it was very clear that she had a pro-[[abortion]] record in the Arizona State Senate and as a state court judge. She was also allied with [[Planned Parenthood]]."<ref name=dflynn>{{cite web|url=https://web.archive.org/web/20120103215640/http://www.flynnfiles.com/blog/phillips/phillips1.htm|title=Interview with Howard Phillips|author=Daniel J. Flynn|publisher=Flynnfiles.com|date=January 3, 2012|accessdate=April 22, 2013}}</ref>