John “Sly” Sylvester, a radio commentator and Democratic operative in Madison, Wis., was dining at a Mexican restaurant in Washington with then-Wisconsin Sen. Russ Feingold about 20 years ago when a young Paul Ryan walked up.

“He was our waiter,” Sylvester said. Feingold knew Ryan’s late father and, as they chatted, Ryan “said he even used to listen to my show when he was a kid,” Sylvester recalled.

Examples like that have helped Ryan, soon-to-be the GOP’s vice presidential nominee, burnish his credentials as a youthful working-class guy.

“I don’t know about you, but when I was growing up, when I was flipping burgers at McDonald’s, when I was standing in front of that big Hobart machine washing dishes, or waiting tables, I never thought of myself as stuck in some station in life,” Ryan recently told a crowd at a high school in suburban Denver. “I thought to myself, I’m the American dream on the path or journey so that I can find happiness however I define it myself.”


It drew big applause.

And yet Ryan, 42, was born into one of the most prominent families in Janesville, Wis., the son of a successful attorney and the grandson of the top federal prosecutor for the western region of the state. Ryan grew up in a big Colonial house on a wooded lot, and his extended clan includes investment managers, corporate executives and owners of major construction companies.

The seeming contradiction appears to have its roots in a family crisis in 1986, when at the age of 16, Ryan discovered his father dead of a heart attack.

The death of Paul Murray Ryan forced the family to make adjustments. Ryan’s mother went back to work. And Ryan took up jobs, as well.


After graduating in 1992 from Miami University, a public college in Ohio, he went to work as an intern and then as a committee professional staffer on Capitol Hill for Sen. Bob Kasten, a Wisconsin Republican, who was defeated that same year by Feingold. When Kasten was voted out, Ryan lost his job. He went to work at the Tortilla Coast restaurant on Capitol Hill, where he ran into Feingold. In 1993, he left behind his hourly job and began as a speechwriter at Empower America, the think tank formed by former congressman and George H.W. Bush Cabinet secretary Jack Kemp and other conservatives, according to a Ryan campaign spokesman.

The spokesman said people could interpret the candidate’s messages about his youth “however they like, but I don’t know that I’d say it’s a message of humble beginnings. Rather a message of hard work and upward mobility. And, of course, work was also important as a young man with the passing of his father while still in high school.”

But there was also more to it than work. Ryan’s rise to political power and financial stability was boosted by family connections and wealth. The larger Ryan family has repeatedly helped the candidate along in his career, giving him a job when he needed one and piling up tens of thousands of dollars in campaign contributions.

In the year after his father’s death, Ryan’s maternal grandmother set up the Ryan-Hutter Investment Partnership, which remains an important part of Ryan’s finances with assets of up to half a million dollars, according to the congressman’s 2011 financial disclosure statement. Ryan continues as the general partner running the entity for the family.


Court records indicate Ryan’s father left a probate estate of $428,000, though the number of assets existing outside the will or the probate remains unknown. Ryan was to receive $50,000 when he turned 30. The will leaves the bulk of the estate to Ryan’s mother, who now lives in an oceanfront condo in Florida.

In addition to the Ryan-Hutter Investment Partnership, Ryan also benefits from another family entity, Ryan Limited Partnership, which was established in March 1995 by an aunt. Ryan’s share of that is worth up to $500,000. Ryan makes no investment decisions in either partnership, the campaign spokesman said.

By the time Ryan had entered Congress in 1999 at the age of 28 and filed his first disclosure statement, he reported assets between $167,000 and $1.3 million, owned a home and had three rental units.

The next year, Ryan married Janna Little, a tax attorney, and his income skyrocketed. (Ryan reported gross income of $323,416 in 2011.)


Of the Ryans’ maximum estimated assets of $7.6 million, Janna’s holdings account for about $6.5 million. She is the daughter of Dan and Prudence Little, two lawyers in Madill, Okla., who over the years have overseen a vast network of land and oil and gas mineral rights in the Red River area straddling southern Oklahoma and northern Texas.

The wealth derived from Janna’s grandfather, Reuel Winfred Little, a self-made millionaire several times over in oil and gas interests and other ventures. He arrived in Madill in 1927 after graduating from the University of Oklahoma law school, with just $25 and a second-hand typewriter. He invented and patented a type of injector used to poison trees, the Little Tree Injector. He made separate fortunes in legal work and redeveloping former military housing.

Meanwhile, the Ryan extended family was building up its own empire in construction, starting with Patrick Ryan, the congressman’s great-grandfather. Ryan’s branch of the family did not stay in the construction business, and Ryan has no financial interest in it today, the campaign spokesman said. But in 1998, when Ryan returned to Janesville to begin his first run for Congress, he briefly took a job with Ryan Inc. Central, a Wisconsin-based road grading company.

The Ryan roots run deep in Janesville.


Patriarch Patrick Ryan sent Ryan’s grandfather, Stanley M. Ryan, to the University of Wisconsin law school, and he was named U.S. attorney for the western district of Wisconsin when he was 24 by President Harding. He rose to prominence in Janesville as a private attorney, serving on a bank board and as chairman of the fire and police commission. When he died, judges from all over the state came to his funeral. Ryan’s father was also a prominent attorney, practicing in Janesville until his death.

Ryan and his family now live in a Georgian Revival home in Janesville that was once owned by the president of the Parker Pen Co. and former chairman of the state Republican Party. The congressman’s aunt, uncle, cousin and brother all live within blocks of his home in the historic Courthouse Hill district.

Since first running for Congress in 1998, Ryan has brought in at least $40,000 in contributions from cousins, second cousins and others in the Ryan Inc. construction business. And that’s not counting money received from his siblings and many other cousins. Ryan’s brother Tobin, an private equity firm executive, has given him $4,250; Stanley, another brother, has given $4,000; and Janet Ryan Rock, a sister, has given $4,000.

ralph.vartabedian@latimes.com


richard.serrano@latimes.com

ken.bensinger@latimes.com

Vartabedian and Bensinger reported from Los Angeles, Serrano from Washington. Times staff writer Alana Semuels in Denver and Marie Rohde and Robert McCoppin in Janesville, Wis., contributed to this report.