[1][2] With a penchant for performing weekly visits to impoverished rural sections of the country, President Medina finished his second term with a 65% approval rate.

Since he was 18 years old he was a student leader, founding the San Juan de la Maguana branch of the Frente Revolucionario Estudiantil Nacionalista at the UASD.

In 1990, Medina was elected member of the Political Committee of the Dominican Liberation Party (PLD) together with Leonel Fernández and Juan Temístocles Montás.

As president of the Chamber of Deputies in the National Congress (1990–94), he was a key figure in congressional negotiations that led to the resolving of the 1994 political impasse.

In that year, a close finish between Joaquín Balaguer and José Francisco Peña Gómez brought about a major conflict, as one side accused the other of fraud.

The agreement eventually worked in favor of the PLD, which won the presidential in the 1996 election, with Leonel Fernández defeating José Francisco Peña Gómez in a second round.

However, Medina concluded he had no chance of overcoming Mejía's nearly 25-point first-round lead, especially after third-place finisher Balaguer hinted some of his supporters would vote for the PRD in the runoff.

Since its foundation the PLD had maintained an implicit non re-election policy, but President Fernández changed that allowing him to campaign against Medina from the Presidential Palace and opt for a second consecutive term in power (his third).

[9] In the evening of 6 May 2007, Medina made a brief public appearance saying he had been "beaten by the state" (in reference to the fact that government resources had been used to suppress his candidacy and to promote that of Fernández).

[13] In the 2016 Dominican presidential election, Medina was re-elected for a second term, defeating the leader of the opposition and PRM candidate Luis Abinader with 61.8% of the votes.

He and other pro-US Caribbean leaders were summoned to a meeting with Donald Trump in March 2019 to define a common policy on the situation in Venezuela and China's "predatory economic practices".

[5] According to genealogist Sinecio Ramírez Suazo, Danilo Medina is allegedly descended from Francisco del Rosario Sánchez, founding father of the Dominican Republic.