Run for resident commissioner

Rosselló began his political career in 1988 when he ran for the office of Resident Commissioner of Puerto Rico, (the island's non-voting observer/representative in the United States Congress) losing to incumbent Jaime Fuster of the Popular Democratic Party (PPD). Nevertheless, he was the candidate from the New Progressive Party (PNP) for whom the most votes were cast in the 1988 elections. This positioned him well to become the party's next leader.

After leading a "Statehood Crusade" throughout the islands of Puerto Rico, in 1991 he became president of the PNP, successfully leading an opposition to a referendum sponsored by the then Puerto Rico's Governor Rafael Hernández Colón. In 1992 he successfully ran for Governor of Puerto Rico, defeating Victoria Muñoz Mendoza of the PPD.

Governor (1993–2001)

As governor, Rosselló launched an anti-crime campaign known as "Mano Dura Contra el Crimen" (literally, "Strong hand against crime") in which the Puerto Rico National Guard was used to assist state police in deterring the ever-increasing crime wave that had begun in the late 1980s. This crime-fighting initiative supposedly managed to reduce violent crimes in half by the time he left office in Jan. 2001, but the figures are disputed due to poor recordkeeping and extensive juking of crime statistics by Puerto Rican police. The U.S. Department of Justice would document these problems with Puerto Rico's police force in a 2011 report. There were also widespread incidents of police brutality, as Rosselló and Police Superintendent Pedro Toledo aggressively deployed riot police against political protests. These protests arose over litany of controversies that marred Rosselló's government, including the privatization of the island's utilities, massive cost overruns and contract disputes on development projects, and several corruption scandals involving top cabinet officials. After Rosselló left office, crime rates either returned to pre-Mano Dura levels or successive governments simply reported more accurate crime statistics. Violent crime declined by a similar extent across the US during that period, but Puerto Rico's crime rate blew past pre-Rosselló levels throughout the 2000s and 2010s.^[6] He also worked to eradicate drug traffic in Puerto Rico Publics School on his campaign "Zona Libre de Drogas" (Drug-Free Zone). The Rosselló government was never able to address the extensive penetration by narcotraffickers of the police and local government, and by 2010 Puerto Rico had one of the highest gun homicide rates in the world, a figure largely driven by drug crime. His administration was also characterized for investing in large-scale, controversial infrastructure projects which included a train system, dubbed Tren Urbano, and a new convention center in San Juan, now officially named^[7] the Pedro Rosselló Convention Center. His policies also included a push towards reducing the size of government and taking government out of areas in which it should not act as a direct competitor of the private sector. His administration reduced the unemployment to less than 11% in 2000 creating thousands of jobs during his 8 years of government. Most of these government and private sector jobs disappeared in the 2000s as the island's debt problem, largely unaddressed during Rosselló's administration, spiraled out of control and forced later governments to purge civil service rolls and resort to regressive tax measures to raise revenue. Some other large-scale infrastructure projects were the Coliseum of Puerto Rico, the Museum of Art of Puerto Rico, Highway 66, and the SuperAcueducto.

Under his administration, a healthcare reform bill was approved. Rosselló's Health Reform made Puerto Rico one of the few jurisdictions in the entire world to have had virtually 100% of its population covered by health insurance. Additionally, under this Reform, Puerto Rico became the only jurisdiction in the US to have nearly 100% of its infants under the age of 2 vaccinated. He led two campaigns for Puerto Rican statehood in 1993 and 1998 in which locally enacted plebiscites were held to consult the Puerto Rican electorate on the political status with the United States. He supported the congressional Young Bill, which sought to carry out a referendum in Puerto Rico to define the political status of the island. However, the bill died in committee in the Senate of the United States. Nevertheless, Rosselló carried out a non-binding plebiscite in 1998 which gave electors four options and a fifth None of the Above column. The opposing Popular Democratic Party led a campaign to boycott the plebiscite and called the electorate to vote for the None of the Above column. The boycott was successful, as the None of the Above column – which did not represent any kind support for any status option – garnered 50.3% of the total votes.^[8]

In the 1996 elections he defeated rivals Héctor Luis Acevedo (PPD) who was mayor of San Juan at the time, and Representative David Noriega (PIP), winning a second term after obtaining more than one million votes and the largest victory margin since 1964.

In 1998, a 45% stake of the state-owned Puerto Rico Telephone Company (PRTC) was sold to a consortium led by GTE (now Verizon) and Banco Popular de Puerto Rico, with another stake set aside to benefit all of the company's employees. This sale led to a general strike organized by several labor unions. A similar attempt to privatize PRTC in 1988, under then Governor Rafael Hernández Colón, led to a similar strike which doomed the sale. The Telecommunications Act of 1996 deregulated the monopolies many regional telephone and cable television companies held. From then on, PRTC's telecommunications monopoly would no longer be able to properly compete in the environment and the losses to the government would have been onerous. The sale price was 2 billion dollars, which union leaders described as "ridiculously low" (PRTC generated about a 100 million dollars of yearly profit at the time of the sale). The privatization of PRTC led to the 1998 Puerto Rican general strike.

Rosello's last term as governor (1998-2001) was plagued with numerous political scandals, many of them related to the use of public funds for personal gain by government officials as well as by members of Rosello's PNP political party. Among the charges was the use of government funds that had been allocated for treating Puerto Ricans suffering from AIDS which were instead used to finance Rosello's political campaign. Some funds intended for public education were also diverted for personal or party gain. After a new governor took over in 2001 (Sila María Calderón Serra) more evidence of Rosello-era scandals was still coming to light.^[9]

Vieques controversy

In April 1999, a U.S. Navy bomber misfired its missiles at a practice range and struck the main watch-post on the island of Vieques, killing David Sanes, a civilian employee of the Navy. The protests that followed on the small island gathered international attention (see Navy-Vieques protests). Governor Rosselló supported the immediate exit of the Navy, appearing before the Senate Armed Services Committee pressing the Senators, among them John Warner and James Inhofe, to immediately take action so that the Navy could withdraw its troops from the island. In 2000, Rosselló and then President Bill Clinton signed an agreement that the Navy would withdraw from Vieques by the year 2003, if voters in Vieques ratified the agreement in a referendum. The agreement included $40 million in public works in Vieques. After Clinton and Rosselló left office, the administration of the next Governor of Puerto Rico, Sila Calderón, rescinded this agreement. Despite political grandstanding from the Calderón administration calling of an earlier withdrawal, the Navy left Vieques on May 1, 2003, the same date President Clinton and Governor Rosselló had agreed upon.

After finishing his term, amid controversy over the growing number of corruption cases involving members of his party and administration, Rosselló moved to the Boston area where he taught on the faculty of the Harvard Kennedy School at Harvard University. He later moved to Virginia, where he first served as a fellow at the Woodrow Wilson International Center for Scholars and later taught public health at George Washington University in Washington, D.C.

In 2003, Rosselló returned to politics and won his party's nomination for the gubernatorial candidacy in a primary election against his successor as PNP leader, Carlos Pesquera. In the 2004 Puerto Rico Elections the PNP won majorities in both houses of the Legislature, the mayorships of 42 of the island's 78 municipalities and the Resident Commissioner post in the U.S. Congress. However, the position of governor was given then to incumbent Resident Commissioner Aníbal Acevedo Vilá who won by razor-thin margin in a highly controversial PR Supreme Court decision that many still hold was politically motivated.

Senator (2005–09)

Prior to assuming office as Senator, Rosselló had announced his intention to remove Senate President Kenneth McClintock and be elected to replace him. An internal power struggle within the New Progressive Party between Rosselló and McClintock led to a split within the NPP Senate delegation in May 2005. After a caucus meeting, eleven of the seventeen senators elected by the New Progressive Party voted for Rosselló, with the other six boycotting the meeting. McClintock and five other senators, Orlando Parga, Luz Arce, Migdalia Padilla, Carlos Díaz, and Jorge de Castro Font, refused to follow the caucus' decision, denying the unanimous consent required by Senate Rules 2 and 6 to remove a president, thus permitting McClintock to remain as Senate president. The party directorate subsequently recommended that McClintock, Parga, and de Castro Font be expelled from the Party, and that Arce, Padilla, and Díaz be censured and prohibited to run for re-election under the party's flag or logo. However, in August 2005 the party's General Assembly only took action to expel de Castro Font, leaving the status of McClintock and the other four senators in limbo after approving in August 2006 a generic censure resolution that did not name any officeholders by name. The sanctions were nullified by San Juan Superior Court Judge Oscar Dávila Suliveres on May 8, 2007. The Supreme Court of Puerto Rico, in a 5-to-1 decision, affirmed the lower court decision. Three of the disciplined senators (De Castro, Arce, Padilla) who ran for renomination, except for Díaz Olivo, were renominated in the March 2008 primary and were re-elected in the general elections.

Rosselló was able to gain a seat in the Senate of Puerto Rico when Victor Loubriel, an elected first-time district senator representing Arecibo, decided to resign his seat two days after being sworn in. The senator's resignation gave the New Progressive Party a seat it could fill, so Rosselló announced his intentions of filling the vacancy and was selected to the post through an internal party procedure. Rosselló officially assumed duties as a Senator of Puerto Rico on February 13, 2005.

On January 16, 2007, Rosselló led the party caucus in the Senate to a reprimand of two more NPP senators, fellow Arecibo senator José Emilio González and Bayamón senator Carmelo Ríos for voting in favor of a concurrent resolution proposing a constitutional amendment that would turn Puerto Rico's bicameral legislature into a unicameral legislative system, increasing the number of reprimanded caucus members to eight of the total of sixteen elected in 2004. Both González and Rios expressed their lack of concern over the reprimand and were handily renominated in the March 2008 primary and reelected in the November 2008 general election.