Jeb Bush's challenges quickly becoming apparent

Former Florida Republican Governor Jeb Bush prior to speaking at the 2014 National Summit on Education Reform in Washington, DC on Nov. 20, 2014. (Saul Loeb/AFP/Getty)
Former Florida Republican Governor Jeb Bush prior to speaking at the 2014 National Summit on Education Reform in Washington, DC on Nov. 20, 2014.
The last time former Florida Gov. Jeb Bush (R) faced a competitive election was literally 20 years ago. After winning an easy primary in 1994, Jeb took on incumbent Gov. Lawton Chiles (D) and lost -- in a year when nearly every Republican in America won big.
Bush tried again four years later, and he won two terms without much trouble, but in campaign politics, politicians who hone their skills on the trail and on the stump have an advantage over those who don't. In Jeb's case, the former governor simply doesn't know what it's like to persevere through a tough primary -- or eke out a win in a spirited general election -- because he's never had to do it.

Former Florida Gov. Jeb Bush blasted the Obama administration's decision to normalize relations with Cuba in a Facebook post Wednesday, but in an example of why Bush's ties to private equity and Barclays could provide fodder for opponents and critics, Barclays (which reportedly pays Bush more than a million dollars a year) had to settle criminal charges for violating sanctions that included Cuba.

Soon after, reports indicated that Bush will abandon his paid advisory position at Barclays in two weeks.
To be sure, it's good to get problems like these out of the way now, and it's wise for Bush to take steps to address pitfalls before the campaign begins in earnest, but I'm not sure he's fully prepared to defend himself against controversies like these. Didn't he and his team see this coming before going after President Obama's breakthrough announcement?
In related news, Nate Silver asked a question the other day that's on the mind of many campaign watchers.

[I]s Bush in the mold of Jon Huntsman and Rudy Giuliani -- candidates who generated lots of buzz among the East Coast media elite but proved too moderate for the Republican base? Or is he more like the past two Republican nominees, Mitt Romney and John McCain, who also were accused of being too moderate but won their party's nomination?

Like Nate, I think it'll be easier to answer that question in the coming months, when we get a better sense of Bush's platform and rivals, but it's probably worth pausing to note that Bush is a climate denier who opposes marriage equality and wants to destroy the Affordable Care Act -- and when it comes to the contemporary Republican Party, he's the "moderate" of the GOP field.
Whether or not that derails his chances remains to be seen, but again, I think it may very well matter that Jeb Bush has no practical experience winning a competitive Republican primary.
* Postscript: If you missed it, Benjy Sarlin had a good report yesterday taking a closer look at the polling on Bush at the national level.