It’s been a yearlong courtship, but no one quite knows if it will pay off.

For the past year, Speaker John Boehner John Andrew BoehnerLongtime House parliamentarian to step down Five things we learned from this year's primaries Bad blood between Pelosi, Meadows complicates coronavirus talks MORE (R-Ohio) has been wooing his longtime friend Jeb Bush to jump into the 2016 presidential race, even as he has shunned potential Tea Party rivals like Sens. Ted Cruz of Texas and Rand Paul of Kentucky.

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Boehner stepped up his lobbying efforts this week, singing the former Florida governor’s praises in a pair of media interviews.

The Speaker’s preference for yet another Bush White House run is partly political, partly personal. He sees Bush as undeniably the strongest, most viable candidate who could pull the party together after a bruising primary and take on a formidable Hillary Clinton, sources said. And the two men are aligned politically, hailing from the same centrist strand of the GOP.

But politics is often personal, and much of Boehner’s desire for a third Bush presidency stems from his decades-long relationship with the Bush family, including Jeb.

The Speaker was first elected to Congress in 1990, when George H.W. Bush was president. In fact, he has said in speeches that his first substantive vote in the House was authorizing the use of military force in the Gulf War, a war that’s inextricably tied with Bush.

It was during the first Bush presidency that he got to know both George W. Bush, the future president, and Jeb Bush, the future Florida governor.

He forged a closer relationship with the Bush family after George W. Bush was elected president in 2000. The Ohio congressman, then the chairman of the Education and the Workforce Committee, teamed up with then-Sen. Edward Kennedy (D-Mass.) to help shepherd the No Child Left Behind Act, Bush’s top first-term domestic priority, through Congress.

Bush signed the education reform bill at Hamilton High School in Ohio, with Boehner standing at his left elbow. Later, they would team up on pension reform after the Enron collapse. And the two golfed together on several occasions.

“This was a very close working relationship,” said a GOP source familiar with the connections between the Ohio Republican and the Bush family. “The president needed a champion on No Child Left Behind, and Boehner was that guy. … Having that champion creates a real bond, because you are working closely together through a 14-month process.”

Boehner also found common ground with Jeb Bush on education. As Florida governor, Bush was a staunch advocate for charter schools and school voucher programs. Boehner has championed a school choice program that would allow underprivileged students in Washington, D.C., to attend private schools.

“When it comes to school choice, they are sort of kindred spirits,” the GOP source said.

Boehner didn’t endorse any GOP primary candidate in 2008 or 2012 and hasn’t officially endorsed anyone in 2016, saying the GOP has “a lot of good candidates.”

But he has talked up Jeb Bush more than any other prospective candidate this year, openly “nudging” the two-term former governor to launch a bid.

“He’s had plenty of opportunities to tell me to stop, and he hasn’t,” Boehner told ABC’s George Stephanopoulos in an interview that aired this week.

Then on Tuesday, he told a Gannett reporter that “competence” will be a defining issue of the 2016 campaign and that Bush “could be a very competent candidate and could make that appeal.”

The Speaker also said Bush “has a record of serious, big reforms” dating to his time as Florida’s governor.

For his part, Bush has said he’s still discussing a White House run with his family and won’t make any decision until late this year or early next year. As the Bush family knows well, a campaign is sure to be grueling, and deep reservations from Jeb’s wife, Columba, have been well documented.

One source said there is a “50-50” chance Bush would throw his hat into the ring. Another made clear that Bush has not asked Boehner to publicly promote his name for president. The two haven’t spoken since they saw each other a year ago at the Jack Kemp awards dinner in Washington. The two had a private conservation that night, aides confirmed.

Bush’s spokeswoman, Kristy Campbell, would only acknowledge that the two men have a strong personal relationship. “Governor Bush and Speaker Boehner are friends and have a mutual respect for one another,” she said.

The same can’t be said of Boehner’s relationship with Cruz or Paul. The Speaker has repeatedly clashed with Rand Paul and his father, Ron, the ex-congressman and perennial presidential candidate.

Just a year ago, Cruz, the combative Texas senator, forced him into a government shutdown that proved politically disastrous; the senator whipped conservative House members against Boehner’s border security bill as recently as this summer.

The Speaker, who has a number of close friends in the Senate, told Gannett he hasn’t spoken with Cruz since the Tea Party senator was elected in 2012. And while he thinks governors make for strong candidates because of their executive experience, Boehner is not particularly close with New Jersey Gov. Chris Christie. They’ve publicly feuded in the past over Hurricane Sandy funding.

Allies of Jeb Bush, meanwhile, argue that his name at the top of the ticket would give Republicans a better shot at winning races up and down the ballot — a belief they think Boehner shares.

“The Speaker, based on his own experience, knows what a challenge it is to bring the Republican Party together. He’s probably looking for somebody at the top of the ticket to bring the party together — not only to win the nomination but to build a coalition for the general election,” said Tallahassee-based consultant Cory Tilley, a former top Jeb Bush campaign aide who later served as the governor’s deputy chief of staff.

Other Florida politicians, too, are rooting for a third Bush presidency.

“Jeb was a terrific governor for our state and has continued positive civic involvement in many projects. He is detail oriented and is genuinely interested in finding common-sense solutions to our vexing problems,” longtime Rep. Ileana Ros-Lehtinen (R-Fla.) wrote in an email to The Hill.

“I’m so pleased to see our Speaker encouraging Jeb to run, and I’m proud to join him in that effort.”