The former Florida governor flirted with presidential runs in 2008 and 2012 but ultimately demurred, always with the flickering possibility of mounting a campaign down the road. But at 61 years old, the second son of former President George Herbert Walker Bush is now likely facing his last shot at the White House.

And the pressure on him to cast aside serious family concerns and enter the 2016 fray is growing. Friends say Jeb Bush’s father is eager for his son to run, even telling a visitor at a recent family gathering in Kennebunkport, Maine, that a presidential campaign and a return of the family dynasty to power was a near certainty. Wall Street financiers and Main Street CEOs eager for a centrist champion are longing for a Bush candidacy.

But people who have met in recent weeks with Jeb Bush in New York, Washington and Florida say they are far less certain that a campaign will ultimately materialize. Some described Bush as deeply engaged on issues beyond his usual focus on immigration and education, suggesting he was very much preparing for a national race. Others said it seemed like concerns over how a run would impact his family ultimately might keep Bush on the sidelines.

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“He told me two things,” a person who spoke with Bush recently in Washington said: “that he knows he has to decide very soon, and that his wife is not at all happy with the possibility.”

This person and several others interviewed for this story declined to be identified by name because Bush has not yet made a decision and they were not authorized to speak publicly on his behalf. Bush himself has said family concerns could keep him out of the race. His wife, Columba, is said to dislike politics and the spotlight — and his daughter, Noelle, has battled substance abuse in the past.

But others in the Bush orbit said the family concerns go well beyond that.

Bush has three grandchildren and a burgeoning business career. A run for president would take him away from all that, possibly for close to a decade. Many of his business dealings would come in for harsh scrutiny and Bush’s efforts to build his family’s wealth would take a big hit during prime years that could otherwise be highly lucrative.

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“He has a really nice life right now, and the question is, does he really want to do this and give that up?” a person familiar with Bush’s thinking said. “And he truly has not decided.”

People who have spoken with Bush say he is much less concerned about the rough ride he undoubtedly would have in the GOP primaries. The party has moved decidedly to Bush’s right in recent years, especially on immigration and education. Bush supports a path to citizenship for the undocumented immigrants in the U.S. and backs national Common Core Standards for public education.

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Bush is already getting a taste on the campaign trail this year of just how unpopular both stands are with the GOP base. In North Carolina this week, Bush campaigned with Thom Tillis and the Republican Senate nominee distanced himself from Bush’s positions. Further highlighting the challenge, Bush’s own son, George P. Bush, declined to say whether he would back his father in a 2016 primary at a Texas Tribune event last weekend, when confronted with his own past comment that Texas Sen. Ted Cruz is the future of the GOP. “I think folks know that I love him,” was all that George P. Bush would say of his dad and the presidential race.

But friends and associates say Bush was prepared for catcalls from the base. They say if he runs, the former governor will absolutely not back off his stances but rather attempt to sell them to his party in the primaries and make the case that he would be the strongest Republican nominee to take on Hillary Clinton or whomever the Democrats nominate.

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“He is well aware of party dynamics, but his view is that leadership matters, a lot,” said Arthur Brooks, a friend of Bush’s and president of the American Enterprise Institute, a conservative think tank. “What he says is, ‘I have strong views on Common Core and immigration and those are views that some people don’t share. But I’m going to provide leadership and ask people to go along with it, and if they can’t — they can’t,” Brooks added. “Isn’t it refreshing to have someone who values truth over victory?”

Another friend said Bush would set out a clear agenda and hope to bring the party along with him. “He might be center-right now instead of far-right, but he is prepared to set out his agenda and take the hits,” the friend said. “He will say, ‘Here are the key things we need to do as a nation on education, tax policy, immigration, foreign policy and national defense’ and then let people decide if they agree.”

Bush declined to comment for this article. His spokeswoman, Kristy Campbell said: “Gov. Bush right now is focused on doing everything he can to help elect great Republican candidates in 2014. As he has said, he will consider whether or not to pursue a bid for the presidency after the midterms elections.”

Friends say Bush is well aware that he will also take hits over his last name and his older brother’s record in office and that he will have to make clear that his would not be a continuation of the George W. or George H.W. Bush presidencies.

It would, however, be a restoration of the family legacy, something said to be very important to the 41st president. A person in attendance at the former president’s 90th birthday party in Kennebunkport this past June said the elder Bush spoke of a Jeb Bush candidacy as a near certainty. The elder Bush is also said to have leaned on his son to run.

Jim McGrath, a spokesman for George H.W. Bush, would not comment on private conversations the former president had during his birthday celebration. But he made no secret of what the elder Bush wants.

“If it were up to the 41st president, Jeb would be a candidate. He is an unabashed promoter of a Jeb Bush candidacy,” McGrath said. “He thinks he would be a fantastic president. But he also respects Jeb’s decision making in what is a very personal matter.”

In the meantime, as Bush tries to make his final decision, he is diving into a heavy travel and fundraising schedule for 2014 GOP Senate and gubernatorial candidates, something outside observers point to as a signal that Bush is leaning toward a run and beefing up his network of potential supporters.

Bush this week held an event in Tampa for Senate candidates Tom Cotton of Arkansas, Joni Ernst of Iowa, Cory Gardner of Colorado, Dan Sullivan of Alaska and Monica Wehby of Oregon. The event raised a total of $750,000, well over the target of $500,000.

He has headlined over two-dozen other fundraisers so far this cycle, including many that brought candidates such as Ed Gillespie (Virginia Senate), Mitch McConnell (Kentucky Senate) and Terry Branstad (Iowa governor) to Florida to tap into the states’ big donor base, bringing fresh money into these campaigns in ways that could pay dividends for Bush in the 2016 primary contest.

Bush is said by those who have spoken to him to be leery of allowing a more strident conservative such as Sen. Rand Paul (R-Ky.) or Cruz to get the GOP nod, something Bush has suggested could lead to a general election landslide for the Democrats. He is also said to argue that Gov. Chris Christie of New Jersey would not be the best centrist Republican candidate and that 2012 nominee Mitt Romney is not likely to run again.

So the direction of the party and its chances in the general election will also weigh heavily on Bush’s final decision, people close to the matter say. But insiders also say the question remains very much a toss-up. And they add that people should not mistake Bush’s 2014 midterm activities as necessarily indicative of a presidential campaign in waiting.

Bush is a popular surrogate every campaign cycle, friends say. It’s just much more high-profile now that he is a possible 2016 candidate. Indeed, if Bush were to come out and say he is not going to be a candidate he would immediately become something less of a draw, both as a campaigner and a highly paid public speaker. So the waiting game plays to his advantage in many respects.

But no one who knows him thinks Bush is playing a game. Instead, insiders say he is truly wrestling with a momentous decision that could alter the course of the rest of his and his family’s life.

“He’s very thoughtful and almost scientific in his analysis,” the person who spoke with him in Washington recently said. “How he comes down on it, I have no idea.”

Mike Allen contributed to this report.

CORRECTION: This story has been updated to clarify that a Tampa fundraising event was not held at Bush’s home.