In March 2014, then-House Budget Chairman Paul Ryan stepped onstage at the Conservative Political Action Conference in National Harbor, Maryland. It wasn’t a great speaking slot, one of the first on that chilly Thursday morning. But Ryan made the most of it, urging his fellow Republicans to embrace new ideas and attempting to repair divisions between its establishment members and Tea Party conservatives.

“There’s a fine line between being pragmatic and being unprincipled,” the Wisconsin congressman said. “And sometimes it’s hard to tell who’s here to start a career and who’s here to serve a cause.”

At the time, Ryan was referring to ongoing battles within the GOP over political strategy, such as whether to raise the debt ceiling or force President Barack Obama’s government into a shutdown. Yet Ryan’s words have taken on new meaning as he attempts to navigate the candidacy of Donald Trump.

Ryan’s actions toward Trump have been puzzling to the celebrity-turned-politician’s supporters, and also his own: At certain times, Ryan, now the speaker, has offered himself to Trump as a willing partner, a bridge to the Republican mainstream. At others, though, Ryan has seemingly gone out of his way to cause trouble for the presumptive GOP nominee, flagging Trump’s comments on a Mexican-American federal judge and adding fuel to the firestorm over his latest allegedly anti-Semitic tweet just as it seemed to be dying down.

Is Ryan being principled or pragmatic?

The answer, friends say, is decidedly the latter.

All of Ryan’s twists and turns and odd gyrations on Trump are in the service of one overriding goal: advancing his own, carefully cultivated agenda of tying the GOP to a series of small-government solutions that would roll back liberal New Deal and Great Society programs — an achievement that has eluded decades of conservative reformers.

This week, the Republican Platform Committee is meeting to formally spell out its policies and principles, and Ryan has a lot riding on the result. He has positioned himself as his party’s intellectual leader with a ready-made agenda for the next Republican president. The House GOP has spent the past six weeks laying out a six-part plan, called “A Better Way,” that touches on everything from taxes to health care reform to defense spending. If Trump wins the White House, he’ll likely have a Republican Congress waiting to pass legislation for him to sign into law. Much of that legislation will likely be found in the GOP platform, making this week a decisive moment for Ryan and his big ideas.

Ryan holds himself up as a quintessential policy wonk — a disciple of Jack Kemp, the happy warrior of supply-side economics — but at his core, he is a politician. In the ongoing battle between pragmatism and principle, Ryan has frequently sided with pragmatism.

No matter who would be the Republican nominee, Ryan always faced a challenge of laying out a governing agenda from the House. But Trump’s allergy to public policy and hesitance to engage on entitlement reform have only exacerbated that task. Ryan will certainly spend the next few months trying to box Trump into an agenda that resembles “A Better Way.” Yet Trump, no fan of in-depth policy plans this campaign, has so far shown little interest in it.

For Ryan, the perils of a Trump presidency extend far beyond his impolitic remarks. In fact, the threat doesn’t even come from Trump himself. Instead, it comes from the millions of conservatives who have supported the real estate mogul, despite his refusal to entertain such Ryan capstones as entitlement reform and extending to his hostility to free trade and immigration.

“He's certainly a threat to what Jack Kemp stood for and to what a lot of us have stood for over the years,” said Peter Wehner, a former George W. Bush White House speechwriter who is close with Ryan and a frequent critic of Trump.

With just a week before the Republican National Convention kicks off, Ryan’s long-term political strategy may be reaching a climax. Through a series of pragmatic political decisions, he has persuaded his House GOP colleagues to back his ideas. But he now must persuade the national electorate to do so as well—all while his own presumptive nominee has shown little interest in supporting the House Republican agenda.

And for Ryan and scores of conservative intellectuals, the rise of Trumpism raises an even scarier question: What if a significant portion of conservative voters aren’t actually interested in his entitlement reforms and don’t subscribe to supply-side economic theory?

Where do they go from there?

Ryan’s ideology has a number of roots — Ayn Rand, Milton Friedman and National Review — but people who know him well will invariably point to his first mentor in Washington — Kemp, the longtime Buffalo-area congressman.

The affable former pro football quarterback was one of the leading supporters of supply-side economics, the theory that cutting taxes would boost the economy so much that tax revenues would actually rise. Kemp first won a House seat in 1971, and his landmark legislative achievement came a decade later with the passage of the 1981 Reagan tax cuts, which cut individual tax rates by 23 percent, including dropping the top marginal rate from 70 percent to 50 percent.

Kemp continued to preach the gospel of supply-side economics in his long-shot 1988 presidential bid, where some Republicans criticized the congressman for focusing too much on growth and not enough on the budget deficit, a divide inside the GOP that would only grow in the years ahead.

After his presidential campaign wilted, Kemp joined his rival George H.W. Bush’s cabinet as head of the Department of Housing and Urban Development, where he dedicated his attention to using monetary incentives to fight poverty, particularly among African-Americans. Kemp championed the idea of “urban enterprise zones,” designated areas that would receive federal incentives to encourage business investment, and he warned about work disincentives in the welfare system, a theory that has been a focal point of Ryan’s own antipoverty efforts.

When Bill Clinton took over the White House in 1993, Kemp joined with fellow former Republican Cabinet member Bill Bennett to co-found the Empower America think tank. Ryan, at 23, landed a job as a speechwriter and staffer there, watching as the former football star gained new battle scars by battling Democrats on taxes and conservatives on fiscal issues, an area where the future speaker would sharply break from his mentor.

In 1994, Kemp came under fire on his right by opposing a California ballot initiative that prohibited undocumented immigrants from accessing the state’s health care and public education systems. He even had names for the growth and austerity wings of the GOP: Like-minded supply-siders were “New Testament Republicans” and deficit hawks like Kansas Sen. Bob Dole, who would pick Kemp as his 1996 vice-presidential running mate, were “Old Testament Republicans.”

In 1995, Ryan went to work as legislative director for then-Rep. Sam Brownback, putting him in the middle of fights over welfare reform and the budget. The Republican-controlled Congress was at odds with Clinton over funding for Medicare, education and public health, leading the government to shut down over 27 days.

Two years later, Ryan got an opening. The Republican incumbent representing his home district gave up his seat to run for the Senate, and Ryan moved back to Wisconsin for a private-sector job and to lay the groundwork for a congressional campaign.

Back in his hometown of Janesville, Ryan developed a platform around fiscal and personal responsibility, pulling freely from his experiences with Kemp, Bennett and Brownback.

“Kemp is a happy pro-growth guy, interested in what happens in our cities, and Bill Bennett [is focused] on the moral agenda and the need for a healthy culture,” said Brownback, now the governor of Kansas. “I think they influenced him dramatically.”

The 1998 election proved disappointing for Republicans hoping the Monica Lewinsky scandal would result in big congressional gains. Instead, voters gave Clinton a small boost and the GOP ended up losing four seats. House Speaker Newt Gingrich quickly stepped down.

Out in Wisconsin’s 1st District, though, Janesville had a new Republican congressman: 28-year old Paul Ryan cruised to victory by 14 points. He would be the second-youngest member of the House.

As a freshman in the Republican-led House, Ryan hewed close to the regime of a back-bencher: He introduced bills on a variety of mostly small-ball issues. Most of them went nowhere.

One of his resolutions honored fallen firefighters. He wrote bills that died in committee to suspend tariffs on air fresheners, bathroom cleaning supplies and motorcycle wheels. He tried to specify how the Census Bureau should list the home addresses of active-duty military service members and their dependents. He offered an amendment to change the rules regarding federal milk prices that failed in the House by a nearly 3-to-1 margin.

But unlike many backbenchers, Ryan also showed a taste for wading into the biggest challenges facing the country. In 2001, he introduced a bill to make George W. Bush’s tax cuts permanent. In 2003, Bush and congressional Republicans were pushing legislation to create a Medicare prescription-drug benefit for seniors. Ryan supported the so-called Medicare Part D proposal but he also signaled his interest then in reforming the entire program to ensure its long-term sustainability.

“This is the only chance we have to make sure we can modernize this benefit for seniors, give them prescription drug coverage that they so desperately need and make sure it is still there for those of you who I see on this panel who are baby boomers when you retire,” he said at a committee hearing that spring.

To Ryan’s critics, his vote for Medicare Part D was perfect evidence of his hypocrisy. How could a fiscal hawk, a man warning about the U.S.’ long-term debt, vote for a new unfunded drug benefit, on top of two new wars and the Bush tax cuts? How could a conservative ideologue vote for a new entitlement?

But for Ryan, the vote was emblematic of another motivation: pragmatism. The new Medicare benefit included an option for seniors to purchase a private drug plan, which Ryan saw as a model for reforming the whole program. “It wasn’t ideal,” Ryan explained in his book, "The Way Forward," about his Medicare vote, “but it moved the ball forward toward broader conservative goals.”

“Long ball is what Paul likes to play, so he’ll make strategic and tactical choices that [build] the ability to make that bigger thing happen,” said John Murray, founder of the Conservative Reform Network, who has worked closely with Ryan over the years.

By the mid-2000s, Kemp’s influence on Ryan was becoming more apparent. Ryan introduced a bill in 2004 mirroring his mentor’s push for national enterprise zones, providing tax breaks for some of the country’s poorest communities. He also co-sponsored dozens of other tax bills overhauling the corporate tax code and permanently repealing the estate tax.

In 2004, Ryan undertook his most ambitious legislative effort yet: privatizing Social Security. His bill would allow Americans to invest about half their payroll taxes in private accounts. At the same time, Ryan was working furiously to make the issue a key plank of Bush’s reelection platform. He succeeded — in part. Bush ran on Social Security reform but adopted a more cautious plan with smaller private accounts.

Even so, the public proved unready for any proposal. “Bush Plan Greeted With Caution,” read a Washington Post headline published just a few months after the president’s second term began. Democrats tore into the idea, and Bush started hemorrhaging political capital from the Iraq War and a botched response to Hurricane Katrina. Democrats picked up 31 seats in the 2006 midterms, flipped control of the House, and Social Security privatization was off the agenda.

Looking back on that experience during the 2012 campaign, Ryan wrote in his book that he told Mitt Romney, “Having lived through the failed Social Security push in 2005, I knew that the next president would need a mandate, not just a victory.” His actions have been driven by that lesson ever since.

By 2007, Ryan’s persistence on Social Security had earned him the reputation as a policy wonk and won him the confidence of leadership, which bucked the GOP’s seniority system in rewarding him the party’s top spot on the House Budget Committee. From this new perch, he had a megaphone to unveil his conservative governing vision. But unveiling that vision and getting Republicans to line up behind it were two different things. It required a pragmatic touch.

He introduced the first of his soon-to-be-famous budgets that March, a document notable both for what was in it and what wasn’t. The bill balanced the budget in five years, but in a section titled, “POLICY OF THE UNITED STATES CONGRESS ON TAXATION,” it included just a single, vague sentence. The policy section on entitlements was equally sparse in the details department.

Politically, Ryan’s first budget made sense. Democrats controlled the House and, as the minority’s proposal, Ryan's blueprint got scant media attention. When it came up for a vote in the House, he lost 40 Republicans.

But Ryan’s wasn’t just a one-act show. He went to work proposing other big ideas, including a health care overhaul that would offer a refundable tax credit for Americans to purchase health insurance and a supply-side tax plan that cut the number of tax brackets from seven to two and reduced tax rates to 10 percent and 25 percent.

A year later, Ryan’s budget had more substance. Now dubbed the “Roadmap for America’s Future,” Ryan folded in his new health care and tax reform plans atop his proposals to change the corporate tax code, block grant Medicaid and privatize Social Security. He was still in the political minority, though, and his resolution garnered just eight co-sponsors and never received a vote.

In 2009, Ryan tried again with his third budget: “Path to Prosperity.” For the first time, his big idea to reform Medicare made it into his fiscal plan with a call to change the program so that beneficiaries could use their government benefits to buy private insurance, an option known as “premium support.”

Even among Ryan’s fellow Republican policy wonks, Medicare reform was considered a politically risky idea. He had met that year to plot out next steps on entitlement reform with House Majority Leader Eric Cantor and several leading GOP thinkers, including National Review’s Ramesh Ponnuru, National Affairs’ Yuval Levin and the Ethics and Public Policy Center’s Peter Wehner. Ponnuru and others argued that reforming Medicaid would make more sense politically. Ryan had other ideas.

“One of the first things Ryan said at the meeting, he described the view he was arguing against as the Ramesh Ponnuru-Dick Morris’ view," Ponnuru said. “And I said, ‘Well, Paul everyone thinks you’re such a nice guy.’”

As expected, Ryan generated controversy by putting premium support in his budget. Democrats argued that Ryan was “ending Medicare.” During the 2012 presidential campaign, one progressive group produced an ad that depicted Ryan rolling a person in a wheelchair off a cliff. Republicans at the time of the debate were politically hesitant to embrace it too. When Ryan introduced his budget for fiscal year 2011, again including the premium support language, just 14 Republicans agreed to co-sponsor it.

Austan Goolsbee, the former chairman of Obama’s Council of Economic Advisers, admired Ryan’s persistence. "He didn’t have to include a plan for Medicare vouchers in his budget,” Goolsbee said. “It has little impact on the 10-year budget. He could have just done a budget that forwarded less controversial Republican priorities and dumped on the Democratic ones."

As Ryan’s stock grew, his proposals garnered more scrutiny, as did his reputation as a deficit hawk. Increasingly, Ryan realized that his ideas were politically scary for his Republican colleagues; getting them on board required deft political maneuvering — what his critics would call lies.

His final budget as the chairman of the Budget Committee, unveiled in 2014, would have slashed government spending by more than $5 trillion, with more than two-thirds of the cuts coming from programs for low-income Americans, according to the left-leaning Center for Budget and Policy Priorities. It also included some broad ideas for reforming the tax code: reducing the number of tax brackets to two (10 percent and 25 percent), lowering the corporate tax rate from 35 percent to 25 percent, and simplifying the tax code, although it didn’t specify further measures.

Ryan held up the document as a picture of fiscal responsibility, but independent observers were less convinced. His broad tax ideas would almost certainly increase the deficit, they said, and Ryan appeared to misdiagnose the underlying source of the U.S.’s long-term debt problems — which is the unrestrained growth of Medicare, Medicaid and Social Security. Instead, the plan slashed nondefense discretionary spending — funding for items like education, housing, health care, the EPA and the IRS — to 1.7 percent of GDP. (It averaged 3.8 percent of GDP from 1974 to 2013.) Of the more than $5 trillion in cuts, less than $900 billion came from Medicare, Medicaid and Social Security.

It was a quintessential Ryan document, a collection of political compromises in service of his larger agenda, enough spending cuts to entice his colleagues but not enough policy details to scare them away.

“When I was working on the Ryan budget, we always had policy assumptions behind everything I did,” said Chauncey Goss, Ryan’s former Budget Committee deputy staff director. “But we didn’t always share those policy assumptions. The confusion — I wouldn’t say [it’s] by design, but there’s opacity there by design.”

That pragmatism also caused his budgets to contradict his other policy proposals. In 2014, for instance, Ryan released an anti-poverty agenda that would expand the earned income tax credit and create a pilot program to combine the funding streams from 11 federal anti-poverty programs into one block grant to the states. It was hailed, even among liberals, as a serious proposal — a conservative agenda for streamlining government and helping the poor, something out of the Kemp playbook. But his proposed budgets would make large cuts to antipoverty spending, including $137 billion to food stamps alone. Ryan’s antipoverty plan, which, as deficit-neutral, made no cuts to programs like foods stamps, was thus incompatible with his budget.

For his strongest critics on the left, that was further evidence that Ryan’s whole reputation as a fiscally rigorous budget wonk is a deliberate charade.

“The dishonesty he sells is closing the budget deficit, but that’s not even smoke and mirrors. It’s imaginary savings,” Paul Krugman, the liberal economist and New York Times columnist, said in an interview. “There’s no evidence at all that he is an actual budget expert that he poses as.”

To Ryan’s associates, there was no contradiction, just a political calculation. “He's got to throw the conservatives some red meat, of course,” Goss said about Ryan’s budgets. “If it's a question of defense or labor, defense is going to get [the money].”

Through his nearly two decades in Congress, Ryan has espoused tax and entitlement ideas that are further-reaching than a lot of his colleagues, even on the right, are comfortable with. And he has steadily recalibrated politically to be sure he’s tugging them along — but hasn’t leaped too far ahead.

In his first budget, for instance, Ryan included Social Security privatization. But with Republicans still scarred from Bush’s ill-fated attempt to privatize the retirement savings entitlement, Ryan removed it. That move wasn’t because Ryan no longer believed in it. Sources close to him explained that it was because Ryan understood that getting his colleagues to vote for a budget that included Social Security reform would be too difficult politically — and would set back his other ideas, including premium support.

“He is an idea-driven politician, and both the noun and adjective should be kept in mind,” Ponnuru said.

The Ryan budget has garnered lots of attention for its spending cuts, but the document wasn’t really about the specific spending cuts; as Ryan writes in his book, it’s a “philosophical document.” At its core, only one policy truly mattered: premium support. There, Ryan succeeded. Republicans eventually rallied around his budgets, some in support of the cuts to nondefense discretionary spending, some for his tax ideas, and others for his reforms to Medicare and Medicaid. But regardless of the reason, Ryan has gotten the majority of his party to support a reform that was once considered politically untouchable. His last budget passed the House, 219-205, with just 12 Republicans in opposition.

“The way he went from his original idea where he had a handful of supporters for his premium support plan to basically every Republican in the House caucus supporting it, that was an amazing achievement,” said Wehner. “Everyone [was] feeling this is the third rail and this is going to kill him. And [even] the handwringers, he got them to go along.”

For all his single-mindedness in pursuit of Medicare reform, Ryan’s actual record in office has been marked by a pragmatic streak in other areas as well. He brokered a face-saving budget deal with Sen. Patty Murray (D-Wash.) in 2013 that helped avert a government shutdown. He’s worked with Democrats on immigration reform. Last year, Ryan shepherded through Congress legislation that made it easier for Obama to pass the Trans-Pacific Partnership trade deal. Only weeks after becoming speaker, he was able to pass bills signed by Obama covering two issues that had stymied Capitol Hill for years: transportation and education.

Ryan has even been willing to adjust his position on premium support. In 2011, he began working with Sen. Ron Wyden (D-Ore.) on a version of the idea, a bipartisan effort to reform Medicare by semi-privatizing it. After consulting with Wyden, Ryan agreed to allow seniors the option to continue with traditional Medicare instead of moving onto a private plan — a public option of the type Republicans disdained when proposed as part of Obamacare. But Democrats turned on Wyden, with the White House saying the Wyden-Ryan proposal would “end Medicare as we know it.” The plan went nowhere.

Despite his sporadic successes, Ryan didn’t come to Washington just to pass two-year budgets and highway bills. He’s here to do something that two generations of tax-cutting, government-shrinking, supply-side conservatives have notably failed to do: reform the entitlement programs and tax code while dramatically shrinking the size of government.

For nearly his entire congressional career, Ryan deemed the House Ways and Means Committee the ideal spot to confront those challenges. Last January, he landed the job as the panel's chairman. But John Boehner’s surprise resignation and Majority Leader Kevin McCarthy's decision to pass on the job eventually forced Ryan to run for speaker. Those close to Ryan say he accepted the position reluctantly, but there’s no denying that his new role has given him a perch to craft an agenda for the entire Republican Party.

That agenda — packaged as “A Better Way” — mirrors many of the policies in the Ryan budget, including block-granting Medicaid and significant supply-side tax cuts. Notably, it also includes premium support.

During his campaign launch speech last year, Trump took a different approach, saying he wanted to “save Medicare, Medicaid and Social Security without cuts.” He's reiterated that promise throughout his campaign. This has created an unexpected challenge for Ryan as he tries to prepare the United States for entitlement reform — the lesson he took from Bush’s failed pursuit of Social Security reform. How can Ryan ready the American people for “A Better Way” when the Republican Party’s nominee appears entirely uninterested in the plan? Even some of Ryan’s friends are skeptical that he can earn a mandate in such an environment.

“There is no way that the House Republicans are going to have a separate identity from Trump,” said Stephen Moore, a senior economic adviser to the Trump campaign and longtime Ryan associate. “It’s just not going to work.”

Ryan was often able to obfuscate his political compromises in his budgets, burying them in vague policy language and spreadsheets full of numbers. But the challenge presented by Trump has laid bare all of Ryan's contradictions. Despite admonishing Trump for a variety of offensive comments, he has not rescinded his endorsement. Why? In part, he says that his institutional role as speaker — he chairs the Republican National Convention — gives him a responsibility to support his party’s nominee. But Ryan also says a Trump presidency is the likeliest path for his ideas to become law. “We clearly have a presumptive nominee who wants to work with us on moving this agenda forward,” he said Thursday after Trump met with House Republicans.

People close to Ryan warn not to view the speaker too much as a master, long-term thinker. Like all politicians, they say, he can’t look too far ahead; the next election always looms. But after 17 years in Congress, the 46-year-old Ryan is clearly working on a time frame greater than two years. He’s well-aware that while he may be able to craft smaller deals under a Hillary Clinton presidency, his deep policy goals such as privatizing Social Security will not happen unless a Republican takes the White House, an effort that becomes harder with each election.

“This work is becoming more and more important with each passing election,” Ryan writes in his book, “because the Republican Party is running into the headwinds of shifting demographics.”

Even with a Republican president, though, the rise of Trump poses new questions for how much conservatives are really behind Ryan’s agenda. As Ryan looked ahead to the 2016 presidential election, his words appear to forecast the rise of a Trump-like figure when he wrote of a “new coalition of Americans looking for leadership that can finally bring our country together again.” But he also said that coalition wanted a candidate to appeal to “the hopes, values and beliefs we share as Americans” who will “engage in the battle of ideas fully.”

By all accounts, Trump is not that candidate. Yet the real estate mogul has managed to appeal to that new coalition of Americans, not with ideas but with negative rhetoric and divisive policies. Millions of Republican primary voters supported Trump even though he has shown little interest in reforming entitlements.

To Ryan’s friends, that makes the challenge harder, but it doesn’t represent an underlying shift in support for Ryan’s ideas. “Terrorism is fresher in the mind than entitlement reform. So the burden of persuasion is higher,” said Rep. Trey Gowdy (R-S.C.). “It’s one thing to have an issue that people are interested in and then persuade them. It’s another thing to have to persuade them to be interested in it and then persuade them.”

For Ryan and his fellow entitlement reformers, the 2016 election represented the best chance to fulfill a goal that has evaded generations of conservatives, a 1980 redux that ushered in a second Republican revolution. Ryan has spent the Obama years laying the groundwork for his agenda, carefully crafting and revising his ideas to win broad support within the GOP. Due to his success at such coalition building, Ryan doesn't need a Reagan-like figure to make his conservative dreams a reality. "The Republican Party has an agenda," said Grover Norquist, the head of Americans for Tax Reform. "We’re not asking for the Republican president to come in like big brother and tell us what to do." Maybe so. But Trump would be unlike any previous Republican president, hostile to free-market policies like free trade and immigration and unpredictable on entitlement reform.

And if Trump loses? At best, the Clinton administration will prove inhospitable to Ryan's agenda, but it will remain the leading platform in the Republican Party. Ryan's sheer perseverance and Kemp-like upbeat demeanor earned him — and his ideas — respect and support among the Republican Conference. But that doesn't necessarily translate into success at the ballot box.

The worst-case scenario for Ryan and his friends: The Republican Party decides that its future electoral success doesn't hinge on embracing the Ryan budget. It hinges on denouncing it.

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