With the year drawing to a close, Jeb Bush found himself accused of being insufficiently conservative and having to defend himself against a fired-up conservative activist base leveling the charge. It’s a familiar story, but this particular case took place fifteen years ago, in December 1999. The email exchange with a pro-life activist was a reaction to Bush’s appointment of a judge while governor of Florida, and it’s part of a massive public-records release of electronic communication by the former governor, reported on in some detail today by the Washington Post. It also sheds some more light on Bush’s 2016 strategy.

For starters, the email exchange with the pro-life activist offers a glimpse into why Bush has been less than intimidated by grassroots opposition to his candidacy: he’s been dealing with this his whole career. Times have arguably changed in the Republican Party since then, and the presidential nomination fight is a different stage altogether. But for Bush, it’s easy to understand why he’s not willing to be deterred by something that’s never been able to stop him before. Here, for the record, is that 1999 exchange, as relayed by the Post:

He regularly sought to calm conservative activists who wanted him to take the government further to the right. In December 1999, Bush tangled over e-mail with an anti­abortion activist who blasted him for appointing a lawyer to a judgeship, because the lawyer had represented the owner of an abortion clinic.

Bush responded that he had not been told about the attorney’s history and, in any case, the lawyer had “received recommendations from many people who I respect.”

Nevertheless, Bush followed up and asked an aide to send the activist a list of all nominees currently before him. “We have no litmus test for judges — we are open to hearing from all Floridians,” he wrote. But he added that the woman “appears concerned about the perceived lack of opportunity to provide input.”

Bush welcomes the debate. That might further antagonize the right, or it might breed a new respect for him for not running from his decisions. But if the latter, it would almost surely be a grudging respect.

Bush has dealt with conservative dissent from his policies since well before there was a Tea Party, and he may think that precedent works in his favor. And maybe it does. But the reverse is just as likely. Conservative grassroots dissent was a different animal before the Tea Party and before new media’s influence on campaigns. Bush faced the low-calorie version of the modern conservative insurgency.

He’ll also face a roster of challengers that offers conservatives the flexibility to take their business elsewhere. But as far as Bush is concerned, conservative anger at him has not slowed him down much, and he seems determined to try to keep the streak alive.

The other aspect to the email archive is how Bush plans to use this transparency to his benefit in the 2016 race. There are two ways this could help him. The first is obvious: these are public records, so if there’s a story in there that portrays him in a negative light, it’s going to come out. He might as well get ahead of the story, spin it to suggest he has nothing to hide to minimize the story as much as possible, and get it out in public early in the race (or even before he’s technically in the race) so it’s old news by the time he’s in the middle of the nomination battle or even the general election.

Bush does not seem to be trying to hide this information in plain sight. To that end, the Post reports, “Bush’s team plans to post the e-mails on a searchable Web site early next year.”

The other way this could help Bush is by building a reputation for transparency. To be sure, what he’s doing is far from revolutionary in terms of what he’s releasing. But by getting it out there and making it easily accessible, he can at least play it as an alternative to the paranoiac secrecy of both the Clintons and President Obama. The Clintons not only famously enforce tribal loyalty but members of their inner circle aren’t above stealing and destroying documents from the National Archives to cover for the Clintons.

The Obama administration promised to be the most transparent administration ever, a phrase that has turned into a punchline. The president, in keeping with the unfortunate pattern of presidential discretion in an age of proliferating media, is more secretive than his predecessors, who were each, while in office, arguably more secretive than their own predecessors, and so forth.

It’s not a surprise, in other words, that the presidential comparison Obama evokes is Nixon. It’s just that the other presidents didn’t make such a big show of lying about their intentions to be transparent. That’s why Obama’s divisiveness is also so noticeable: he promised healing, and spent six years and counting turning Americans on each other. (Related: the Democratic Party wants you to harangue your family members with pro-Obama talking points over the holidays. Merry Christmas and happy Chanukah from the creepy statists running your government.)

The result of Obama’s Music Man routine will undoubtedly be increased cynicism toward politicians. So anyone making similar promises as Obama made during his campaign should beware the poisoned well. But if anyone can realistically promise a true transparency, it might be Bush, who could try to claim that you don’t have to wait for him to take office to test his commitment since he displayed transparency during the campaign.

Transparency is not now, and not ever going to be, an issue that catapults someone to the presidency. (You could argue “trust” is, but that’s not the same thing.) So the benefit to Bush of releasing these emails is almost surely about trying to waste news cycles on any revelation to inoculate his campaign from them later. As for his fifteen-year battle with conservatives, that too may be old news, but it’s precisely the kind of old news that feeds grudges and gains steam over time. Bush would be foolish to believe he can run like it’s 1999.

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