Jeb Bush Has 99 Problems: Seriously, Here They Are

In many ways, Jeb Bush is sitting pretty. He's the only major 2016 candidate who has publicly announced he's actively exploring a presidential run and is busy hauling in cash for his Right to Rise PAC. He's sitting atop many national polls of GOP contenders, and the media has anointed him the early fundraising leader.

The main flaw of all this Jeb-for-president talk, however, is that the bored national political media has little else to do besides jabber and write about Jeb Bush. In the two months since he announced he's exploring a run, countless ink has been spilled on Bush's political, personal, and business past and analyzing any campaign pitfalls that may come his way. On one hand, it's good for Jeb to get all of this out of the way early. On the other hand, it provides a convenient playbook for any of his would-be rivals on how to attack him.

How much scrutiny has Bush already faced? It didn't take us long to round up 99 problems already written about Bush's potential path to the White House.

1. George W. Bush is his brother. [Almost Every News Outlet Ever]

2. And he has hired many of George W. Bush's old national security advisers from the Iraq War days as his advisers. [CNN]

3. He has no foreign policy experience. [Politico]

4. The above was apparent when he bungled facts and pronunciations during his first big foreign policy speech. [The Daily Beast]

5. He says he'll "be his own man" but still hasn't really explained how many of his policies would be different from his brother's. [LA Times]

6. Seriously, explaining how he would deal with foreign policy in regard to his family legacy appears to be the main tenet of his foreign policy spiel right now. [Time]

7. He's also George H.W. Bush's son, and apparently he'll struggle under this "dynasty thing." [Chicago Tribune]

8. But as a young man, he had no problem taking advantage of his family's connections and privilege. [New York Times]

9. Back when his dad was VP, he lobbied the Reagan administration on behalf of a guy who would turn out to be a massive Medicare fraudster. [HuffPost]

10. A young Bush also tried to use his dad's connections to get Americans to eat more rabbit meat. [Breitbart]

11. There was that whole Terri Schiavo episode. [The New Yorker]

12. And Michael Schiavo is still ready to be a thorn in his side. [Miami Herald]

13. He signed Florida's controversial "Stand Your Ground" law. [Newsmax]

14. He also championed that 10-20-Life minimum sentencing bill. [Times-Union]

15. Which has attracted controversy lately thanks to the Marissa Alexander case. [HLN]

16. He may have a hard time persuading a lot of Republican primary voters to agree with his views on immigration. [USA Today]

17. Indeed, he once called illegal immigration an "act of love." [Washington Times]

18. But a lot of conservatives still really, really do not like his views on immigration. [TownHall]

19. As governor, he supported a law to issue undocumented workers driver's licenses. The conservative media, including Fox News, regularly go into a tizzy when Democrats support such laws. [AP]

20. Yet it's still not entirely clear what his plan on immigration would actually be. [WaPo]

21. But even Obama is gently picking at problems and differences between Jeb and the rest of the GOP establishment on immigration. [Raw Story]

22. He really, really supports Common Core. [WaPo]

23. And a lot of conservative voters really, really do not. [Boston Globe]

24. Sen. Ted Cruz even came to Bush's home state to badmouth the ex-guv's stance on Common Core. [Sunshine State News]

25. Turns out Jeb and Obama have a lot in common when it comes to education. [The Tampa Bay Times]

26. And speaking of Obama, where does Jeb really stand on Obamacare? Does he secretly love it? [Talking Points Memo]

27. He's an introvert! [Politico]

28. Who has baggage. [The Hill]

29. Some people think he's boring -- but not his mom! [NYDN]

30. A poll shows that 64 percent of voters associate Jeb with "the past." In contrast, 50 percent see Hillary Clinton as representing "the future." [Tampa Bay Times]

31. He's not conservative enough and is a "squishy moderate." [Breitbart]

32. Or he's conservative enough, but nobody knows that yet. [CNN]

33. Or he's too conservative! [Salon]

34. Yet some right-wing outlets think he's an establishment candidate who will "pander" to conservatives. [Daily Caller]

35. And he might not have quite as easy of a time at that as the moderate Mitt Romney did. [Salon]

36. But remember that time he said Ronald Reagan would be too moderate for today's GOP? [AP]

37. His polling numbers aren't great. The Real Clear Politics average shows him leading with just 14.5 percent. Wisconsin Gov. Scott Walker is only a point and a half behind. [RCP]

38. He hasn't run for office in 12 years and might not understand Twitter. [ Politico]

39. Because of that, an Obama adviser compared him to Cutty from The Wire. [CNN]

40. Seriously, his social media game is far from "on fleek." [NBC News]

41. Some worry he's better at governing than campaigning. [WaPo]

42. Will he truly be able to understand millennials? [Pando]

43. His chief technology officer resigned only a few days after being appointed because he forgot to delete tweets making fun of "sluts" and gay men at his gym. [Buzzfeed]

44. That guy also had some interesting things to say about Martin Luther King Jr. [Politico]

45. Jeb's first fundraiser was hosted by a guy who owned a firm that ripped off Florida taxpayers. [New Times]

46. He championed fracking while working for a private equity firm that was about to purchase a bunch of tracking wells. [Tampa Bay Times]

47. He has a hardline stance on the Cuban embargo, which is not really the mainstream view anymore. [Miami Herald]

48. He once worked for a bank that violated the Cuban sanctions, though. [BuzzFeed]

49. In fact, his entire banking career could be an impediment. [CNN]

50. Remember that time he worked for Lehman Brothers? [Tampa Bay Times]

51. He was a board member for a company that aggressively championed Obamacare. [New York Times]

52. The Marco Rubio situation. [ABC News]

53. Also, apparently, something about Lindsey Graham. [Bloomberg]

54. In 1994 he compared those who practice sodomy (AKA homosexuals) to "polluters, pedophiles, pornographers, drunk drivers, and developers without proper permits." [Buzzfeed]

55. He was also against gay adoption as recently as 2004. [PolitiFact]

56. And his recent comments on gay marriage are calculatedly wishy-washy. [Free Press]

57. He lost the battle on Florida's popularly passed class-size amendment more than a decade ago but for some reason is still talking about it. [Herald-Tribune]

58. Sometimes his speeches might be a little bland. [The New Republic]

59. He once presented Hillary Clinton with an award, which a conservative group has turned into a very, very scary video. [WaPo]

60.He doesn't like Iowa, and Iowans don't like him. [The Tampa Bay Times]

61. No, seriously. A new poll shows him in fourth place with just 10 percent in Iowa, the early primary stronghold. [USA Today]

62. Which is especially troubling because both his father and brother won Iowa. [Daily Beast]

63. In a recent poll of Illinois Republican voters, he's not doing too great either compared to Scott Walker. [HuffPo]

64. Walker, meanwhile, was widely seen as taking a shot at Jeb recently when he reiterated during a speech that he didn't inherit either fame or fortune from his family. [Daily Mail]

65. He might be seen as "too bold" or as a bully. [U.S. News & World Report]

66. Prep school classmates say he was definitely a pot-smoking bully with bad grades. [Boston Globe]

67. And he did admit to smoking pot in high school. [VICE]

68. He was also put on probation at his school for underage drinking. [Vanity Fair]

69. And he's getting called a hypocrite for opposing marijuana legalization. [Mediaite]

70. Yes, despite all of that youthful pot smoking, he came out to strongly urge Floridians to vote against medical marijuana last year. [New Times]

71. He accidentally released some Floridians' social security numbers online. [The Verge]

72. Bush's own mother, Barbara, has repeatedly said things like she thinks America has already had enough Bushes in the White House. [New Times]

73. But she finally came around and retracted those views in a somewhat embarrassing fashion. [New Times]

74. And Conan O'Brien was quick to make fun of the mommy issues. [News Busters]

75. He really likes to golf, which all presidents seem to get dinged on. [Tampa Bay Times]

76. He's already being taken to task by fact-checkers for citing some untruths. [The Hill]

77. His wife once took out loans to buy $90,000 of jewelry at Mayors. [WaPo]

78. His son got caught having sex in a car in a parking lot. [GLAPN]

79. His daughter got arrested on drug charges. [The Daily Mail]

80. His wife was reportedly annoyed by the amount of time Jeb was spending with a female aide during his 1998 run for governor. [NYTimes]

81. His wife, by the way, avoids the spotlight and doesn't like politics. [Bustle]

82. People are already making Jeb Bush-themed YouTube parody videos. [Bloomberg]

83. Charles Barkley likes him. [Politico]

84. He still doesn't appear to be an old he-coon who walks before the light of day. [MSNBC]

85. His views on NSA data collection are rubbing some "civil liberties"-concerned libertarians the wrong way. [Daily Caller]

86. A right-wing media site is exasperated with the incompetence of his media staff. [Breitbart]

87. During his last year at the governor's mansion, he blindsided Florida libraries by using a line-item veto to cut their funding by $5.8 million. Librarians were very upset. [ALA]

88. Dan Quayle has returned from oblivion to help him raise funds. Yes, Dan Quayle. [WaPo]

89. The Tea Party. [FiveThirtyEight].

90. "Jeb" isn't even his real name. Or a real name. They're his initials. What's the deal with that? [Twitter]

91. Bill Maher says Jeb converted to Catholicism just to win elections. Americans tend to be fine with a politician's religion as long as its Jesus-y enough, but Jeb would be America's first Catholic-convert president. [Salon]

92. Right-wing talk-radio hosts don't like him. [WaPo]

93. Seriously. Rush Limbaugh said yesterday that Jeb shares Obama's "flawed America" worldview. "Jeb thinks America is flawed, and he wants it to be something else," said Limbaugh. [Mediaite]

94. Rand Paul doesn't think he's electable. [Breitbart]

95. And Rand is out there producing and posting fake phone conversations between Jeb and Hillary on Twitter like he's a morning-radio shock jock instead of a U.S. senator. [WaPo]

96. Donal Trump is also taking shots at him. [CBS News]

97. Frank Zappa ruined some great humanizing campaign material (AKA wedding photos). [USA Today]

98. He has pissed off the Beastie Boys. [Bloomberg]

99. A gay "bear" couple in Oregon owns JebBushForPresident.com and will use it as an attack website. [Rachel Maddow, MSNBC]

See? Those are 99 reasons you won't hear much from the Hillary Clinton would-be campaign for a while.

Follow Miami New Times on Facebook.

KEEP MIAMI NEW TIMES FREE... Since we started Miami New Times, it has been defined as the free, independent voice of Miami, and we'd like to keep it that way. With local media under siege, it's more important than ever for us to rally support behind funding our local journalism. You can help by participating in our "I Support" program, allowing us to keep offering readers access to our incisive coverage of local news, food and culture with no paywalls.
Kyle Munzenrieder