2016 PR PNP Governor and Resident Commissioner Primaries

Perceived as a lock for the nomination between November of 2012 and September of 2015—should Ricky Rosselló not run (Per Early Polling)—Pierluisi's second term as Resident Commissioner was widely seen as a success.

Here, he was the only Statewide PNP  reelected in 2012 got a plebiscite bill passed through the house, mountains of federal funds, and worked to get the Fiscal Adjustment Plan and PROMESA acts through the house of representatives

As a result of this, plus his earlier 1993-1997 Stint as Secretary of Justice under Ricky Rosselló's father Pedro Rosselló, Pierluisi ran on experience, noting that in the present fiscal crisis Puerto Rico needed a steady hand in order to put its fiscal house in order and attain statehood.

Rosselló on the other hand—originally signalling he would run for the Resident Commissionership—went directly for the governorship; coasting upon his name, his father's grassroots support, and the support of the person likeliest seen to succeed Pierluisi: Jenniffer González Colón to try and win the nomination.

Here, he ran a hope & change, populist-eske campaign—running as the front runner (he had 61% in the November 2014 ENDI Poll)—Dr. Rosselló highlighted his status as a political outsider with new ideas while opposing spending cuts or firing public employees

However, rather quickly his star began to fade; here, the institutional suport Pierluisi had as the leader of the PNP began to pay dividends. 

In holding most of the mayoral endorsements—and a large chunk of legislative endorsements—Pierluisi was able to cut Rosselló's 2014 share to 47% (with himself at 30%) by November 2015, and then tie Rosselló 47-47% in March

Announcing a few Days before Ricky Rosselló, and inmediately holding a Rally with him, Jenniffer was seen as a lock for the position throughout the campaign. 

Despite this, Pesquera thought he saw an opening to become resident commissioner by joining himself to Pierluisi as González Colón had done with Ricky, joining the race in September after the first big momentum shift against Ricky, should he get Pierluisi's support he thought he could beat Jenniffer

However, this was not to be, lacking in Pierluisi's institution advantages—Pesquera got significantly less institutional support than his ticket mate—all of it plus some people who were neutral in the governorship going to Jenniffer González.

As a result of this, he trailed Jenniffer throughout the Campaign—with the final poll placing the contest at Jenniffer with 76% to Pesquera's 19%.