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As Bush considers a 2016 presidential bid, he has tried to insist "I am my own man," in order to differentiate himself from his older brother, former President George W. Bush, and father, former President George H.W. Bush.
But the intrigue into the high profile family isn't dying down.
"I'm a Bush, I'm proud of it. Like what am I supposed to say?" Jeb Bush quipped to reporters this week in New Hampshire, according to The New York Times.
At the same event, Bush said, "I love my mom and dad. I love my brother, and people are just going to have to get over that."
However, the former Florida governor has struggled in recent days with how to handle questions about his brother, whose controversial tenure in office includes the widely unpopular invasion of Iraq in 2003. Indeed, George W. Bush reportedly said "me" last month when asked about obstacles to his brother's candidacy.
"It's an easy line to say, 'Haven't we had enough Bushes?' After all, even my mother said, 'Yes,'" he said, according to Politico.
But George W. Bush, Jeb Bush's elder by six years, may be able to shed some light on navigating the tricky family dynamic, as the older brother was similarly hounded by familial questions during his political career.
Here's how George W. Bush has responded to questions about his famous last name and the legacy of his father:
In 1978, during George W. Bush's bid to win a Texas congressional seat
When his eldest son was a contender for Congress, George H.W. Bush had just left his post as director at the CIA, a role he assumed after serving as the US ambassador to the United Nations.
In light of his father's high profile, George W. Bush faced claims he was an entitled New Englander during the campaign.
"We've been attacked for where I was born, for who my family is, and where my money has come from," Bush told the Midland Reporter-Telegram in 1978, according to a New York Times article in 2000. "I don't think that's fair."
"I can't abandon my background. I'm not trying to hide behind any facade," he said in separate comments, adding that despite the connections of his famous father, "We don't need dad in this race," according to the Associated Press.
Reuters/Michael Boddy
During the 1994 campaign for governor of Texas
"Bill Clinton drove the agenda against my father. My father let Bill Clinton decide what issues the two of them were going to talk about. That was a major mistake," he told the New York Times.
"Incumbents have to project into the future, offer a fresh vision. My father didn't do it."
During the 2000 presidential election
Early in his 2000 campaign for president, George W. Bush's father was attacked by other Republicans vying for the party's nomination in a GOP primary debate.
"I will let my dad defend himself. My dad will go down in history as a really good president. His record stands for itself. I'm the person who's running for president," he said after the debate, according to the Philadelphia Inquirer.
"He's an extraordinary man. I know people may disagree with my
On George H.W. Bush's infamous decision to renege on 'read my lips, no new taxes' campaign promise
"I think the mistake was to say, 'read my lips' ... and then raise the taxes," he told ABC's Barbara Walters in 2000.
"I think it undermined some of his credibility, particularly with Republicans and fiscal conservatives," Bush said.
AP Photo/Don Ryan
And in 1998, here's how George H.W. Bush's advised his sons on how to deal with family comparisons:
The elder Bush, famous for writing hand written letters, penned a note to both his sons in 1998, when they were launching their respective political careers and trying to step of of their father's shadow.
"At some point both of you may want to say 'Well, I don't agree with my Dad on that point' or 'Frankly I think Dad was wrong on that.' Do it. Chart your own course, no just on the issues but on defining yourselves," Bush wrote, according to a copy of the note that was published in a book of his letters, "All the Best."
"Nothing that crowd can ever say or those journalists can ever write will diminish my pride in you both, so worry not. These comparisons are inevitable and they will inevitably be hurtful to all of us, but not harmful enough to divide, not hurtful enough to really mean anything. So when the next one surfaces just say 'Dad understands. He is at my side. He understands that I would never say anything much less do anything to hurt any member of our family.'
"So read my lips - no more worrying."