(Bloomberg) — Hillary Clinton’s circle wants to be quoted
yawning at Jeb Bush, a sure sign of concern that he could beat
her in 2016.

“He’s got his own party to run in, and I will be very
impressed if he makes it through that primary system,” Paul
Begala, a longtime adviser to Clinton and her husband, said
after Bush announced this week that he is “actively exploring”
a presidential run.

Make no mistake. Clinton’s team and other Democrats already
are trying to figure out how to take on Bush, and there’s no
early consensus. They could portray him as a shadow of his
brother, President George W. Bush, as a moderate who can’t make
it through his own party’s primary, or as a candidate who is too
conservative to win a general election.

A Bush-centric e-mail that EMILY’s List sent to its donors
on Wednesday took the latter approach.

“Jeb Bush made it official. He’s exploring a run for
president,” reads the graphic embedded in the fundraising pitch
from the group that supports women candidates who back abortion
rights. “As governor, he called himself the ‘most pro-life
governor in modern times.’…Imagine what he’d do as
president.”

A button at the bottom of the e-mail says “Help us get
ready to hold Jeb Bush accountable. Donate.”

Stephanie Schriock, the president of EMILY’s list, is often
mentioned as a possible campaign manager for the former First
Lady. Jess McIntosh, a spokeswoman for the group, sought to
portray Bush as too conservative for the American electorate.

‘Their Side’

“Jeb Bush is going to spend a long time reminding everyone
how conservative he is on these issues,” she said. “Voters are
going to see that he’s not on their side.”

Yet at the same time, the Democratic super-PAC American
Bridge released a Web video replete with clips of Republican
commentators and news reporters saying Bush will struggle to win
over conservatives. The group counts high-profile Clinton donors
among its benefactors.

Jaime Harrison, the chairman of the South Carolina
Democratic Party, said that if Bush runs and wins the Republican
nomination, he’ll struggle to galvanize the conservative base
because he’s endorsed the Common Core education standards
reviled by many in the Republican Party and speaks warmly of
undocumented immigrants.

Harrison said that while it’s important to appeal to
independent voters, a modern presidential campaign has to
energize its party’s grassroots to win.

Clinton spokesman Nick Merrill declined to comment on Bush,
following her team’s protocol when it comes to discussing
potential 2016 rivals.

‘Too Conservative’

Candidates are always trying to define their rivals for the
voting public, and Democrats often pick the tag “too
conservative” for Republicans. President Barack Obama’s aides
believed they had a choice in running against Mitt Romney in
2012, between calling him a flip-flopper or a far-right
conservative. It was former President Bill Clinton who said the
flip-flop tag wouldn’t stick.

Romney’s the other Republican, besides George W. Bush, to
whom Democrats would like to compare Jeb Bush. Democrats were
able to use Romney’s wealth, and the ways in which he attained
it, to argue that he was out of touch with the needs of most
voters.

And the one anti-Bush theme that is a common refrain among
Clinton-aligned groups and longtime advisers is that his
business ventures will hurt him. He started two private equity
funds this year, including one, BH Global Aviation, that’s
incorporated in the U.K. and Wales, allowing foreign investors
to avoid taxation in the U.S.

‘Benedict Arnolds’

“He would be the first president who organized overseas
tax havens for billionaire Benedict Arnolds,” Begala said.

Bush will give up his role as a senior adviser at Barclays
Plc, according to a person familiar with the matter who asked
not to be identified because they were not authorized to speak
publicly.

Whatever approach Democrats choose, it’s clear they’re wary
of Bush. One veteran Clinton adviser said that he is probably
the strongest Republican nominee, citing his moderate positions
on education and immigration that don’t sit well with
conservatives but hit home with independent voters.

The adviser, who spoke on the condition of anonymity, said
Bush would benefit in a general election if he can survive the
primary without pandering to the Republican base on those issues
— both because his positions appeal outside the Republican
Party and because it would show him to be a candidate of
conviction.

Bush Fatigue?

“As I look at the Republican side, he’s an adult in the
room that commands respect and the kind of conservative that
Wall Street and other Republican establishment types can get
behind,” said Democratic strategist Rodell Mollineau. “The one
downside is his last name’s Bush and there’s still fatigue in
this country.”

Like Mollineau, Begala acknowledged Bush could be a strong
candidate, if he makes it to a general election.

“Since he’s likely to run as a Republican, I think it’s
more of a question for potential Republican candidates than
potential Democratic candidates,” he said. “The guy is
formidable. He’s impressive.”

If some Democrats try to sound more blase, it’s rooted in
other reasons. Clinton’s political allies don’t want to feed the
Bush-Clinton throwback hype that has tantalized cable-news
producers. The battle of the dynasties talk isn’t helpful to her
if she ends up winning the Democratic nomination and facing
someone not named Bush. And there’s no reason to elevate a
potential heavyweight.

‘Act of Love’

Part of the challenge for Democrats is that Jeb Bush
himself has staked out varying positions on issues, such as
illegal immigration. In April, he described families that
decided to come to the U.S. as breaking the law. “But it’s not
a felony,” he said. “It’s an act of love.”

By last month, he moved closer to his fellow Republican
hopefuls when he criticized President Barack Obama for using
executive powers to protect as many as 5 million undocumented
immigrants from being deported. And on Wednesday, he described
Obama’s decision to begin normalizing relations with Cuba after
a five-decade embargo a “foreign policy misstep.”

His recent moves toward a run, including a forthcoming e-book on his years as governor and yesterday’s Facebook
announcement about his decision-making process, have been
greeted warmly by veteran Republican Party political operatives
and coolly by a younger generation that identifies more closely
with the Tea Party.

Paul, Cruz

Kentucky Senator Rand Paul and Texas Senator Ted Cruz are
leaders among the latter set and could be part of a large field
of Republican candidates vying for conservative votes.

For the first time in decades, there could be multiple
candidates fighting for the middle-of-the-road mantle in the
Republican primary, including Governor Chris Christie of New
Jersey.

Mike Duncan, a former chairman of the Republican National
Committee, said the expansion of the Republican field is a sign
of strength.

“Historically, we have not had as level a playing field
with as many entrants in a long time,” Duncan said. “This is
relatively new territory for us.”

Duncan pegged 1964 as the last time the Republican Party
offered such a strong set of contenders across the ideological
spectrum. That year, the party nominated Barry Goldwater, who
won the support of a young Hillary Rodham Clinton but lost the
election to President Lyndon Johnson. His opponents included New
York governor and future vice president Nelson Rockefeller,
Governor James Rhodes of Ohio, UN Ambassador Henry Cabot Lodge
Jr., and former Governor Harold Stassen of Minnesota.

To contact the reporter on this story:
Jonathan Allen in Washington at
jallen149@bloomberg.net

To contact the editors responsible for this story:
Craig Gordon at
cgordon39@bloomberg.net
Heather Smith