After pulling strings to get his daughter into Walter Payton College Prep, Bruce Rauner, a Republican candidate for governor, became one of the elite Chicago public high school’s biggest benefactors.

The Rauner Family Foundation gave $250,000 to the Payton Prep Initiative for Education on Dec. 14, 2009 — about a year and a half after Rauner called then-Chicago Public Schools CEO Arne Duncan to overturn his daughter’s rejection for admission, records examined by the Chicago Sun-Times reveal.

Rauner’s gift was the largest the not-for-profit foundation had received up to that point. It amounts to nearly 30 percent of all the money the group has gotten during its first five years, according to records the Rauner and Payton charities have filed with the state.

Rauner’s gift to the Payton Prep Initiative came two months after his foundation gave $500,000 to the Chicago Public Schools Foundation, run by the school system’s top administrators. His foundation previously had given money to that organization.

Rauner, a venture capitalist, called Chicago school officials in early 2008. Within days, his daughter was admitted to Payton for the 2008-09 academic year by the school’s principal, according to a source familiar with the matter.

The gubernatorial hopeful has said little about his daughter’s admission to Payton, dismissing it as “stuff that doesn’t matter.”

On Saturday, Rauner’s aides declined to elaborate on specific questions about his daughter’s admission to Payton. Two weeks ago, Rauner’s campaign spokesman Mike Schrimpf said Rauner’s daughter “was admitted off the principal’s list, the same way many students have been admitted.”

Rauner has never publicly discussed his donation to the Payton Prep Initiative, whose board members included Payton’s then-principal, Ellen Estrada. She has since retired and couldn’t be reached for comment.

“The contribution to the Payton Prep Initiative was made more than a year and half after the Rauners’ daughter was admitted to the school and was intended to fulfill both current needs as well as to help solidify the endowment,” Schrimpf said. “The Rauners always generously contribute to the schools their children are attending.”

Rauner and his wife run the foundation. They raised their six children in Winnetka, where students typically attend prestigious New Trier High School.

BIGGEST GIFTS

Here are the largest donations the Rauner Family Foundation has made between Jan. 1, 2009, and Dec. 31, 2011. The foundation had assets of $50.7 million as of the end of 2011.

1. $500,000 to Donors Trust, Alexandria, Va., 2011

2. $500,000 to Children First Fund: The Chicago Public Schools Foundation, October 2009

3. $400,000 to Stand For Children Leadership Center, Oregon, 2010

4. $300,000 to Teach for America, Chicago, 2011

5. $250,000 to Dartmouth College, Hanover, N.H., 2011

6. $250,000 to Teach for America, Chicago, 2010

7. $250,000 to Payton Prep Initiative for Education, Dec. 14, 2009

8. $250,000 to Teach for America, Chicago, 2009

9. $250,000 to Dartmouth College, 2009

10. $200,000 to the Family Taxpayers Foundation, Carpentersville, 2010

Sources: Illinois attorney general, Internal Revenue ServiceRauner called Duncan, and a top Duncan aide reached out to Estrada, the Payton principal who admitted Rauner’s daughter, according to the source.Rauner’s daughter didn’t make the cut. It isn’t clear which Chicago address she listed on her application. Rauner owns residential property in Chicago.For reasons Rauner has never explained, his daughter applied in 2008 to attend Payton — a selective-enrollment CPS school that rejected most white applicants unless they had straight ‘A’ report cards and scored very high on the entrance exam.

It was one of dozens of admissions to CPS’ selective-enrollment high schools that were made based on “political clout, favoritism, preferential treatment and violations of selection and enrollment practices and policies,” a 2010 investigation by the Chicago schools’ inspector general found. As a result, principals were given less influence over the enrollment process.

Estrada also served on the board of the Payton Prep Initiative, which raises money for the school with another not-for-profit — the Friends of Payton Association, a parent-run organization created when the school opened in 2000.

Before the Rauner foundation’s gift, Friends of Payton had more money than the newer Payton Prep Initiative.

Rauner’s gift allowed the Payton Prep Initiative to triple its spending, to $223,772, in the 2009-10 school year, according to state records. Those records do not show how the money was used, but the Payton Prep Initiative’s website says it spent $100,000 on computers for the school around that time.

“I wasn’t at Payton when the donation was made, so I have nothing to offer in way of commentary,” says Estrada’s successor, current Payton Principal Timothy Devine.

Devine, a son of former Cook County State’s Attorney Richard Devine, also is now on the Payton Prep Initiative board.

Other Payton Prep Initiative board members declined to comment or didn’t return messages.

The Payton Prep Initiative is aiming to create a $3 million endowment for the school, according to its website. It had assets of $557,855 as of June 30, 2012.

Friends of Payton had $87,406 in assets as of that date. That group raises money to support extracurricular programs, including athletics and student travel.

Rauner, who has never previously run for public office, made $53 million in 2012, according to his tax return. He is president of the Rauner Family Foundation, which had $50.7 million in assets as of Dec. 31, 2011, according to the most recent records filed with the state.

Since 2008, the Rauner Family Foundation has contributed $872,000 to the CPS Foundation, also called the Children’s First Fund. That includes the $500,000 donation in October 2009, about two months before the donation to the Payton Prep Initiative.