The former Florida governor is one of the names often mentioned as a contender for the 2016 Republican nomination. He hasn't ruled out seeking it, but he hasn't committed to it either. He's thinking about it and will make a decision later this year.
In the absence of a firm answer, there is naturally plenty of speculation about whether Bush will try to keep the political family's dynasty alive. Recent news coverage has largely focused on how his family will be the key factor in his decision.
Running for the highest office in the U.S. is very much a family affair. Spouses and children are expected to be on the campaign trail, their personal lives are also put under the microscope. For a Bush, there is baggage and a brand to protect.
"If Jeb Bush were to get [the nomination], the entire Bush family would be on the ticket," said Lara Brown, an associate professor at George Washington University’s school of political management.
His wife, Columba, is said to be the one who will ultimately determine whether he runs. He won't do it without her support and she's not known to relish the spotlight that comes with campaigning and being a political wife.
She endured it when her husband ran and lost the Florida governor's race in 1994, an event that strained their marriage. She was there in 1998 when he tried again, and stood by him after he won and served two terms.
Jeb would make 'great president'
She may not be up for it again, especially given that presidential races are particularly brutal fights, and the possibility of being the president's wife is a whole different ball game than being a governor's wife.
The couple, who met in her native Mexico when Bush was a young exchange student, has three children. Eldest son George P. Bush has political ambitions of his own and is currently running for Texas Land Commissioner. He wants his dad to go for it.
Daughter Noelle, on the other hand, has kept a low profile since her arrest more than a decade ago for prescription fraud. She struggled with drug addiction and like her mother, prefers to keep private. Jeb Bush Jr., who also has an arrest record from his early 20s, for public intoxication and resisting arrest, now works in his father's web of business endeavours that include real estate and consulting.
Then there are the former Bush presidents. The elder George Bush, now 89, reportedly wants his son to run and the younger George said his brother would make a "great president."
His mother, however, is not so enthusiastic.
"There's no question in my mind that Jeb is the best-qualified person to run for president, but I hope he won't ... There are other families. I refuse to accept that this great country isn't raising other wonderful people," she told C-SPAN. No more Kennedys, Clintons, or Bushes, she suggested.
Do Republicans want another Bush?
Let's assume Bush ignores his mother's wishes, the rest of his family is on board and he's ready to take the plunge. The next logical question might be: are Americans ready for him? Do they want another Bush in the Oval Office?
George W. Bush left Washington after eight years as one of the most unpopular presidents in American history, according to approval rating polls.
Brown, the GWU professor and author of Jockeying for the American Presidency, said there's another question that must be asked first and that's whether Republicans themselves are willing to accept another Bush.
"I think the answer to that is quite frankly, no," she said, adding that the GOP may want an outsider and while Bush hasn't worked in Washington, it will be difficult to disassociate from his brother and father who have.
Bush would undoubtedly have to answer for their legacies during a campaign, while simultaneously establishing his own reputation. He's known in Florida and his native Texas, but would have to win over Republicans in primary races in key states such as Iowa.
"It's sort of futile to think about the eventual [presidential] race because the real question is would he make it through the nomination and I think that's highly unlikely," said Brown.
Clinton vs. Bush in 2016?
Tea Party and libertarian Republicans, whose momentum gained strength partly in reaction to Bush 43's big-spending policies, according to Brown, will not line up behind this Bush. They are critical of his more moderate education and immigration positions and they want the likes of Ted Cruz or Rand Paul to run instead.
Bush does, however, have supporters in the GOP establishment who are urging him to run and are laying the groundwork. He's the kind of candidate the party needs, some argue. He's known as a policy wonk and has the intellect that some believe his brother lacked. He's fluent in Spanish and his Mexican-American family could appeal to Hispanic voters, a demographic the Republicans need to get onside. He would have instant access to a broad network of financial backers through his family and his own connections.
Bush has a choice to make. Does he continue working in the private sector, earning millions, and shielding his family from the attention that comes with public service? Or, does he go after a job that some think should have been his in the first place, not his brother's?
The Bush name could both help and hurt him if he decides to put his hat in the ring. If he does, and he wins the nomination, he could be up against someone who knows the benefits and burdens of a famous name all too well – Hillary Clinton. Depending on how events unfold, the 2016 election could end up being a family feud over the White House, pitting one dynasty against another.