What Jeb Bush's Email Trove Reveals About Him

Likely 2016 presidential candidate Jeb Bush announced earlier this month he would release 250,000 emails from his eight years as governor of Florida, describing the trove as "some funny ones, there's some sad ones, there's some serious ones," according to an interview with WPLG-TV, ABC News' Miami affiliate.Bush said he would release them early next year in a searchable format, but the Washington Post got an early look at the massive cache through an open records request. Here are the five things we've learned from the Bush emails, so far:

1.A Look at Constituent Emails, Even the Unpleasant Ones

One of the more fascinating bits of insight we learned from the email release, thanks to the Washington Post, is just how much Bush was directly emailing with constituents, even angry ones. One man wrote Bush, "politicians make me sick, you make me sick." The then-governor replied: "I am truly sorry you feel that way. Have a nice day."

He then added a smiley face, showing he wasn't just an early adopter of email, but emoticon use, as well. In another exchange, a woman wrote to him inquiring about the date of his wife's birthday, and he quickly replied.

In another, a man wrote to Bush about what the Washington Post describes as a "messy domestic struggle between friends." The man writes, "what should have been a messy divorce, seems to have turned into a criminal matter; with me in the middle." Bush proceeded to take at least some sort of action, forwarding the email to an aide and asking her to look into the matter. It's an interesting peek into the detail he took to deal with matters affecting Floridians, and how much he aggressively used email during his time as head of the state.

2.Emails Live Forever and He Knew It

We may know now that emails live forever and can end up becoming public at any time, but even in 1999 Bush knew one day the world could be reading his daily correspondence and nothing in email form is truly private. In a December 1999 message to staff, Bush ended a back and forth about vacation time by predicting this day would come, writing the messages "might make a newspaper one of these days." Bush said, "I suggest that you guys have a verbal conversation about it rather than create a public document. :)"

Florida does have extensive public-records laws, another reason Bush may have known it was likely, or at least possible, the emails could be released publicly one day. It does allow for some exemptions, including legal issues. Despite the open records laws, Bush has said he's going to release the trove as a sign of "transparency," a likely nudging at his possible 2016 rivals on both sides of the aisle.

3.How He Deals With Angry Conservatives

In the short period of time since Bush announced he will "actively explore the possibility of running for president of the United States," there has been some backlash from the more conservative wing of the GOP. It's not a surprise and will likely become much louder when, or if, he officially gets in the race. The emails show it's nothing new for Bush and he has been dealing with angry members of his own party judging his conservative bonafides since he was first elected.

In one exchange, Bush was going through emails after 10pm and he forwarded an angry one to top aides. The email called Bush "NO CONSERVATIVE" and Bush noted he was answering these kind of emails himself. He wrote to his advisers, "Kind of scary and I am very tired." In another from December, 1999, he tried to calm an anti-abortion activist who was angry Bush appointed an attorney to a judgeship because the lawyer had also represented the owner of an abortion clinic. Bush wrote back and told the conservative activist he had not known about the lawyer's history and the attorney had "received recommendations from many people who I respect." He did follow up and asked an aide to send the emailer a list of all the nominees who were currently before Bush. "We have no litmus test for judges - we are open to hearing from all Floridians," he wrote. Bush then added that the activist "appears concerned about the perceived lack of opportunity to provide input."

4.Cuba and a Bill Clinton Swipe

In an email exchange from January 1999 with then-Rep. Lincoln Diaz-Balart on Cuba, Bush appears to take a jab at President Bill Clinton, who was still in office serving out his last year. In the interaction, which is also interesting considering the recent Cuba news, Bush promised not to budge on any possible changes to Cuba policy and the embargo. In the back and forth, Bush tells Diaz-Balart the next president could be harder on Cuba than Clinton, writing, "Forceful diplomacy can make a difference and we have had none for the last seven years and the current President is preoccupied with other matters."

Clinton was still entangled in the Monica Lewinsky investigation. Last week when President Obama announced he would move to begin to normalize relations with Cuba, Bush objected, calling it a "policy misstep." The emails show he has remained consistently against any thawing of relations.

5.What the Everyday Was Like and Emails on Campaign Finance Reform

The emails also reveal what issues and details Bush was dealing with day-to-day. The Post describes it as Bush "personally respond(ing) to job applicants, press(ing) aides for details on invitees to events and engag(ing) with hundreds of constituents." Issues he dealt with covered in the emails include "education, taxes and health care between 1999 and 2007," all of which will be closely examined in the run-up and during any campaign for the White House.

Bush also received a "daily immigration update," as well as "briefings on protecting the citrus industry, and even "memos about preparing for Y2K," the computer bug that was predicted to possibly cause chaos when the new year turned from 1999 to 2000. He was also emailing about issues like campaign finance reform with a GOP donor and South Florida developer, Al Hoffman. Hoffman wrote to ask Bush about supporting a campaign finance reform bill introduced in the state legislature, even mentioning Bush's brother. "Your brother thinks it's the right thing to do also, as do I, although I think you are wise not to address it this year," Hoffman wrote to the governor. "I favor campaign finance reform that doesn't put us at a disadvantage," Bush replied to Hoffman, adding a bill introduced in the legislature "would do just that." As for the more casual, the emails show Bush wasn't always formal, writing "awesome," "my bad" and "chill out" throughout his emails.