(CN) - Pop star Shakira's ex-boyfriend, Antonio de la Rua, filed a second lawsuit demanding $100 million, which he claims is his share of the singer's profits.
De la Rua, the son of former Argentine president Fernando de la Rua, sued the Columbian singer in Los Angeles Superior Court.
Shakira Isabel Mebarak Ripoll, the newest judge on NBC's 'The Voice,' has sold more than 70 million albums, had dozens of chart topping hits, and was appointed President Obama's Advisory Commission on Educational Excellence for Hispanics.
Shakira and de la Rua dated for 11 years, beginning in 2000. In 2006, the couple signed a prenuptial agreement agreeing to leave the relationship with only what they entered with, according to the complaint. But de la Rua claims the agreement only covered their personal belongings like homes and property.
De la Rua originally sued Shakira in November 2012, after the couple broke up, claiming she owed him $100 million for his work managing her career.
The pop star claimed de la Rua had never been more than a boyfriend and a trusted advisor and sought to have the lawsuit dismissed on the grounds that the New York County Supreme Court was not the proper venue.
On April 12, de la Rua sued Shakira again under identical claims, this time in Los Angeles Superior Court.
De la Rua claims Shakira asked him to manage her career after a 2004 world tour in which her former rep walked away with millions while the tour flopped.
He says he played a pivotal role in the development of "the Shakira brand" as that of a viable international pop star, and that she left him no choice but to sue after she terminated their partnership.
And he claims to be the architect of some of the most important decisions in her career, including talking her into recording "Hips Don't Lie" to appease record executives. That song turned out to be the biggest hit of her career at the time.
De la Rua says he has no proof that the two ever agreed to be financial partners, other than multiple emails from Shakira, detailing the state of the partnership and saying how much she appreciated his guidance.
Lisa Tsai with Reid, Collins, & Tsai in Austin, Texas and William Reid, Rachel Fleishman, Jeffery Gross and Gregory Schwegmann with the firm's New York office are representing de la Rua.