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Stumbling out the gate for the last six months, 62-year-old former Florida Gov. Jeb Bush makes it official in Miami tomorrow announcing as a 2016 Republican Party candidate. Jeb comes with considerable baggage, the brother of one of the most unpopular presidents in modern history, finishing his two-terms Jan. 20, 2009 with under 30% approval ratings. Jeb’s brother, former President George W. Bush, lived and died by the Iraq War, deciding to topple the late Iraqi dictator Saddam Hussein April 10, 2003. Since then, the U.S. government spent trillions of tax dollars, lost nearly 4,500 lives and drove the economy into the worst recession since the Great Depression. Carrying his brother’s burden, Jeb hopes to start fresh with his own campaign but the voting public still hasn’t forgotten his brother’s train wreck. Only recently, Jeb admitted he wouldn’t have gone into Iraq.

Bush’s public relations team has spent lavishly over the last six months, helping him climb to the top of the GOP rankings in a crowded 2016 GOP field. “I think the transition to a candidacy will allow me to be more direct about my advocacy of the leadership skills necessary for the next president to fix a few things,” Bush told CNN, not saying what he’d do differently than President Barack Obama or, for that matter, other conservative GOP presidential candidates. “And as a candidate,” Jeb said. “I’ll be more specific on policy,” already boasting front-runner status among the growing list of Republicans candidates. Bush’s name recognition has helped his candidacy, without doing much to prove himself in 2016. Portraying himself in campaign ads or giving prepared stump speeches has helped Jeb leapfrog other of high-profile Republicans presidential hopefuls.

Jeb has about a two-month free ride before he’s put to the test in the first GOP presidential debate scheduled Aug. 15. No matter how much Jeb’s already schooled himself as a presidential candidate, the former Florida governor hasn’t shown the rhetorical flourishes in spontaneous press interviews, especially when asked recently about whether or not he would have gone to war in Iraq. Jeb reluctantly said if he knew then, what he knows now he wouldn’t have gone into Iraq. When you consider his father, former President George H.W. Bush, was president, he didn’t march to Baghdad in the 1991 First Gulf War. Jeb didn’t know his father’s reservations for toppling Saddam, especially the dreaded power vacuum that would have brought terrorism and anarchy to the region. Today’s anarchy with the Islamic State of Iraq and Syria is attributable to toppling Saddam.

When Bush faces the firing line in the first debate, he’ll either sink or swim relative to the smoother talkers on the campaign trail. Despite polling only four percent, compared to Bush’s 12%, New Jersey Gov. Chris Christie, should decide to run, promises to do far better than Bush in presidential debates. Unlike his brother “W,” Jeb lacks the spunkiness and churlish sense to humor that unnerved former Vice President Al Gore in 2000. Jeb plays things as a straight arrow, sometimes looking like a deer caught in the headlights when asked tough questions without preparation. “The barriers right now on people rising up is the great challenge of our time,” said Bush, not saying whether or not he’s referring to immigration. Unpopular with conservatives, Jeb believes, like “W,” that it’s only fair to help undocumented Latino workers find a path to legal status or citizenship.

Whatever head start Jeb gets from the Bush name, it’s going to evaporate quickly once he faces the press or getting into a spontaneous debating situation, regardless of all his preparation. Bush’s big advantage over many of his fellow GOP candidates is his affable disposition, avoiding course rhetoric that makes his colleagues less appealing. Expected to do well in New Hampshire, Bush finds himself polling poorly in Iowa and South Carolina. Despite raising about $100 million by the end of June, if Bush stumbles in the debates, it could cripple his ability to raise cash through Super Pacs or political action committees. Out of politics sine 2007, Bush hasn’t been battle tested recently in political circles. Getting into the ring with the likes of Sen. Marco Rubio (R-Fl.), Sen. Ted Cruz (R-Texas), former HP CEO Carly Fiorina, New Jersey Gov. Chris Christie, Gov. Scott Walker (R-Wis.), could cause problems.

Jeb’s long-awaited announcement for 2016 GOP candidate could deflate an already shaky start to his presidential campaign. Reluctant to hazard opinions on Obamacare, the Iraq War, Supreme Court, abortion, same-sex marriage, immigration, etc., Bush finds himself caught between a rock-and-a-hard-place on key issues confronting his campaign. There’s only so much equivocation tolerated in Bush’s candidacy before his polls head south. “There are some real problems for Jeb,” said conservative TownHall.com columnist Erick Erickson, referring largely to Jeb’s lack of conservative credentials. Jeb’s moderate credentials and affable personality are his best assets moving forward in 2016. Bush’s Achilles Heel won’t be his stump speeches or prepared interviews. How Bush does under the bright lights in GOP debates will make or break his candidacy.