De Castro Font was also a member of the United States Army Reserve, and served briefly with the Puerto Rico National Guard.

The elections resulted in a "mixed" government with PPD's Aníbal Acevedo Vilá as governor, and the PNP dominating both the House of Representatives and the Senate.

De Castro did not recognize the party's decision to expel him and continued to identify himself both as a supporter of statehood for Puerto Rico as well as a member of the PNP.

The Supreme Court of Puerto Rico, in the case McClintock vs. Rivera Schatz, annulled De Castro Font's expulsion from the party in a 5–1 decision.

On July 8, 2008, it was reported that De Castro Font was under investigation for fraud and corruption by the FBI, which was based on testimony by witnesses interviewed regarding a second case.

[6] On August 23, 2008, the Federal Bureau of Investigation raided the Senator's Capitol office, a San Juan, Puerto Rico gas station at which he was a client and his Hato Rey apartment after obtaining a search warrant from U.S. District Court Judge Francisco Besosa.

To this, Senator De Castro Font responded aggressively and threatened to reveal information that could link many members of the party in illicit activities, including Fortuño and his wife.

[citation needed] On September 9, 2008, De Castro Font voluntarily arrived at the Federico Degetau Federal Building in San Juan to "turn himself in" after allegedly receiving a phone call that morning from a close friend of Fortuño's, advising him that he was to be arrested that day.

[citation needed] On September 10, 2008, San Juan District Court rejected the pleas of the PNP to expel Jorge De Castro Font from the ballot for the upcoming elections.

The judge determined that once a candidate has been elected in a primary by the people and has been officially certified by the Comisión Estatal de Eleciones, "he or she cannot be removed for reasons other than those specified by law".

[9] The case is prosecuted by the Criminal Division's Public Integrity Section headed by Chief William M. Welch II, and investigated by the FBI's San Juan Field Office.

On December 4, 2008, de Castro was arrested and jailed indefinitely for violating his bail conditions when, according to Federal District Court Judge Francisco Besosa he has at least three improper contacts with government witnesses.

[14] On December 21, 2008, in a letter to PNP President and Governor-elect Luis Fortuño, he announced that he was resigning the seat to which he was elected in the upcoming Senate scheduled to take office on January 2, 2009.

[22] In 2011, as a result of De Castro's legal troubles and incarceration, it was speculated that his ex-wife, Lisandra, could either be charged with him locally for tax evasion, or serve as a witness against her ex-husband.