Former Secretary of State Hillary Clinton meets with people during a book signing on June 10, 2014 in New York, N.Y.
Photo by Dennis Van Tine/Geisler-Fotopres/picture-alliance/dpa/AP

What would a Jeb Bush-Hillary Clinton matchup in 2016 look like?

Updated

It’s beginning to feel a bit like 1992.

Former Florida Gov. Jeb Bush announced Tuesday that he will “actively explore” a presidential bid, potentially setting up a 2016 battle against former Secretary of State Hillary Clinton, whose husband unseated Bush’s father, George H.W. Bush, 22 years ago.

But unlike 1992, the potential clash between two of the biggest political dynasties in American history would have the air of a family feud – both personally and in the politics each represents.

RELATED: Jeb Bush announces he’s exploring a presidential run

In their respective party primaries, Bush and Clinton would run on parallel tracks – close to the middle while taking flack from the flanks – and in a general election, they might neutralize each others’ biggest strengths and weaknesses, since they share so many. 

The Bush and Clinton families have become close since either one occupied the White House. Bill Clinton has made a habit of visiting George H.W. Bush at his home in Maine every summer, while Jeb Bush literally presented Hillary Clinton with an award.

“Bill’s father wasn’t around,” Barbara Bush told CSPAN of the man who pushed her husband out of office. “I think he thinks of George a little bit like the father he didn’t have.” She added: “I love Bill Clinton.”

George W. Bush calls Bill Clinton his “brother from another mother” and Hillary Clinton his “sister-in-law,” while he and his predecessor clearly enjoyed each others’ presence at a joint appearance in September to launch a scholars program run jointly by their presidential libraries.

Jeb Bush chairs the National Constitution Center in Philadelphia, which presented Hillary Clinton with an award in March. “Hillary and I come from different political parties, and we disagree about a few things, but we do agree on the wisdom of the American people — especially those in Iowa and New Hampshire and South Carolina,” Bush joked.

And some observers think this bonhomie could make for a more substantive presidential race than any in recent memory. Mark McKinnon, a top adviser to John McCain’s 2008 presidential run, thinks Clinton vs. Bush would be “great for America.” They’re both qualified, both represent the ideological middle of their parties, and would both engage in civil and substantive policy debates in a time of hyper-partisanship, he wrote in a widely read column for The Daily Beast.

McKinnon founded a group that promotes bipartisanship in Washington called No Labels, along with Nancy Jacobson, a longtime Clinton adviser and strategist. They succeeded in getting bipartisan groups of lawmakers to sit next to each other at State of the Union addresses.

But on the other hand, there will be plenty of people in both parties unhappy with another Clinton-Bush face-off. Liberals and conservatives alike might view the matchup as lacking real contrast, while others – including Bush’s own mother – worry about the corrosive effect of political dynasties on American democracy.

“We’ve had enough Bushes,” Jeb Bush’s mother told the “Today” show in April. (She has apparently come around on another Bush since then.)

And polls consistently show Americans fed up with their current leadership, suggesting there’s a desire for a fresh face and new thinking. 

“It’s great that George W. Bush and Bill Clinton and the Bush and Clinton families get along so well these days, but the Republican Party’s base is not going to entrust the task of beating Hillary Clinton to her metaphorical brother-in-law,” wrote National Review’s Jim Geraghty.

Meanwhile, many Clinton allies view Bush as her most formidable potential opponent. “The presidential will be in my view a very tough race. I would think that a Jeb Bush and a Rob Portman – just as a hypothetical – would be a strong ticket for them,” former Clinton White House political director Harold Ickes told reporters last month.  “Can a Democrat win the White House without both of Ohio and Florida? The answer is yes, but it then has to be a perfect storm.”

Portman, a Republican senator from Ohio, announced earlier this month he would not be a presidential candidate in 2016.

Both Jeb Bush and Hillary Clinton would be strongly favored by their party’s establishment and ideological center, and both would face opposition from their party’s base, though Bush’s primary fight would be infinitely more difficult. While Clinton is leading the handful of other Democrats looking at a run by more 50 percentage points, Bush is locked in a crowded race and faces a Republican base that disagrees with him on key policies.

In a Bush vs. Clinton general election, partisan attacks on either candidate would take on a new layer of awkwardness as the caricature they try to point of their opponent might look familiar in the mirror.

RELATED: Hillary Clinton steers clear of thorny issues

For instance, Republicans have been trying to portray Clinton as an out-of-touch elitist who has spent her whole life in politics – a difficult charge to level if their own candidate is the multi-millionaire son of a former president.

American Bridge, the Democratic opposition research super PAC run by a key Clinton ally, has attacked Bush for “his involvement with several questionable private sector companies,” and dismissed Bush’s political career as a product of  “the Bush family’s political prestige and deep connections to Republican Party donors and influencers.”

Of course, Republicans could say the same could of Clinton.

“There are some people that’ll say there’s no way I’m going to vote for somebody with that name,” George W. Bush said last month of his last name. “Of course if he were to run against Hillary Clinton then I think the name issue would somewhat dissipate.”

On Tuesday, Democrats and Clinton allies were loathe to speak publicly about Bush, but said privately that the difference would be in Bush’s policies. Even if Clinton and Bush have some similarities in their biographies, Clinton supports policies that help average Americans, while Bush would not.

Bush’s early announcement timing also represents an alternative approach to Clinton’s. Some top strategists around Clinton pushed her to announce an exploratory committee as early as November or December of this year, but they lost the argument to the group advocating a slower schedule.

“Some in the orbit argued that Hillary should form an early exploratory committee. The winning argument was that her timeline should be well-thought-out and personal,” said one Clinton ally who opposed the early effort.

Bush lacked the pre-campaign outside infrastructure Clinton has now, which may have pushed him to get in sooner.

Bill Clinton, George H. W. Bush, George W. Bush and Jeb Bush

What would a Jeb Bush-Hillary Clinton matchup in 2016 look like?

Updated