Bush rolled out his cybersecurity plan recently in a meeting with tech leaders in Seattle, while continuing to blast Clinton: "It should not be too much to ask government officials to abide by the laws and rules in place to safeguard our national security."
And when he released his emails from his time as governor in an e-book last month, "Reply All." his campaign blasted out a website and video with a clear message: Bush is an "open book" and Clinton is "elusive and evasive."
But a 2002 trade battle between Bacardi and Cuba over the rights to the "Havana Club" label shows Bush's transparency has its limits and shows some details are missing from the Bush email repository.
A string of emails from Bush personally weighing in on the Bacardi fight when he was governor of Florida were not among any of the releases. Their existence is only known because a Florida investigative reporter obtained them years ago.
Bush has released hundreds of thousands of emails from the private email server he used to conduct state business when he was governor from 1999-2007. And the state of Florida released an even more comprehensive batch of emails, including emails sent to his official state email address that were not on found in his public release.
But even all those gigabytes are still missing some incisive emails -- like an April 2002 directive from Bush to his then-chief of staff with a clear message about the rum lobbying fight: "this is ridiculous. let us discuss."
The New York Times
pointed out that Bush may have broken state public records retention laws earlier this year, after he waited seven years to provide the state with 25,000 emails from his time as governor. And a group run by veteran Democratic operative Brad Woodhouse filed a complaint last month
, saying that Bush should face the misdemeanor charge of withholding records -- punishable by up to a year in prison or $1,000.
But it's unclear if Bush broke any laws by not releasing every email from his time in office.
Kristy Campbell, a Bush campaign spokeswoman, did not say what happened to the missing emails, instead she touted Bush's "unprecedented commitment to transparency."
"Today a full permanent archive of nearly 300,000 emails reside with the Florida Department of State, above and beyond Florida retention policies. To make them even more accessible, Jeb launched jebemails.com earlier this year," Campbell said in a statement.
She continued: "With regards to Bacardi in general, there are numerous emails in his archive that discuss Governor Bush's posture on this issue in addition to public press reports citing his advocacy. His longstanding support for Florida-based companies and opposition to both government confiscation of private property and the Castro regime in Cuba are well-documented."
Campbell said Monday that there "is no comparison" between Bush and Clinton, alleging Clinton did "everything possible to circumvent transparency" and "(endangered) classified information."
Bush's involvement in the rum fight began in earnest January 2002, when a top Republican donor and the president of Bacardi rum's U.S. operation went to Bush with a simple plea, laid out in an email subject line: "BACARDI NEEDS HELP." Bacardi was embroiled in a patent fight with French liquor giant Pernod and Fidel Castro over the world-renowned rum label "Havana Club." And Bacardi was losing, badly.
For years, Bacardi had unsuccessfully argued that the Pernod-Cuba claim to the label should be voided because Castro wrongly wrested control from a private owner in the Cuban Revolution.
In 2002, Bacardi turned to Bush, whose older brother had taken the White House a year earlier, to make its case. And Bush quickly set his team to work, fighting to get the "Havana Club" label for Bacardi.
Among the emails not made public by Bush, but documented by Florida investigative reporter Dan Christensen earlier this year
, is the reply from Bush's then-chief of staff Kathleen Shanahan that their early efforts for Bacardi had not worked and "we may need to move up the food chain."
The Bacardi emails were not in copies of Bush's emails provided to CNN by the Florida Department of State in response to an open records request. They also were not found on Bush's email website -- which includes a smaller set of the batch released by the state.
When the Department of State's office was later asked for the emails not publicly released, an official said it would take several weeks to process. The office, the official said, is preoccupied with a larger review
sparked by the accidental release of social security numbers in the Bush emails.
Questions about government work emails and private servers have become a major issue for Clinton.
Clinton's use of a private email server and the sending of classified information over an unsecured server spurred her to make a surprise apology to voters. She continued fending off questions about her email server telling The Des Moines Register's editorial board recently that "there is no evidence at all that my server was breached" and even joking, when asked about transparency: "Well, you can count on me not to have a private email server."
The FBI is in the process of recovering Clinton's emails as part of a Justice Department review. Republicans have argued her personal email server could have compromised national security, there are ongoing investigation into her email by both the U.S. government and Congressional Republicans and Clinton herself will testify under oath about her email next month on Capitol Hill.
During a campaign swing through Nevada last month, Bush likened Clinton to former Army private Chelsea Manning and former National Security Agency employee Edward Snowden -- who released troves of sensitive U.S. government information and are either in prison or facing jail time.
"I mean, we got problems with our federal government firewalls obviously, but to have a private server in your home, I mean, come on, man," Bush said last month
. "That doesn't pass the smell test."
Questions about gaps in Bush's email release are hardly new, Politifact Florida found
that his statement "I released all my emails" was "Mostly False" and ticked down a list of reasons, including the determination he only released 51% of the 550,000 emails he said he had from 1999-2007. Bush was required to turn over emails that had to do with state business. Under the law, according to Politifact, Bush is entitled to decide which emails pertained to state business and which ones are personal.
The Bacardi lobbying is one of the first looks at just what details are missing from the Bush email repository.
At the time, Jorge Rodriguez-Marquez, the president of Bacardi-USA, Inc., was embroiled in the legal battle trying to wrest control of the "Havana Club" name. The label is a top commodity and Rodriguez-Marquez had argued before the Clinton administration and then the Bush administration that Cuba had no rights to the name.
More than a dozen relevant emails about the battle were found in the state of Florida public records response, and a smaller number were found in Bush's own release last December. But some of the most relevant ones -- tying Bush to calls for direct action for Bacardi -- were missing from his much-trumpeted data dump.
Copies obtained by Christensen, a veteran Florida investigative reporter, a decade earlier, were posted to the nonprofit news site he now edits, FloridaBulldog.org
, in February.
They fill in key gaps from the Bush emails publicly released at his website JebEmails.com
A Bacardi executive told CNN that the fight for the "Havana Club" label is actually ongoing, and taking "longer than what Bacardi expected."
"To put the referenced e-mail correspondence into context, the dispute surrounding Havana Club rum has been going on for more than 20 years," Rick Wilson, Bacardi's senior vice president for external affairs, said in a statement. "Then-Gov. Bush was responding to inquiries by Mr. Rodriguez and Bacardi to determine what was taking so long in what Bacardi believed to be rather routine measures after the company purchased the legitimate global rights to the Havana Club trademark from the creators and original owners, Jose Arechabala S.A. and the Arechabala family."
A Bacardi spokeswoman said that Rodriguez-Marquez had retired from the company. But in a 2003 Washington Post article about the dispute he said, "Florida businesses and citizens expect they may turn to the Governor's office when their legitimate and legally resolved issues are in jeopardy."
Rodriguez-Marquez spurred Bush's intervention with the January 8, 2002, email, the first of many, sent with the all caps subject line.
Before asking Bush for help, Rodriguez-Marquez detailed the international legal fight and dropped key names, including that of long-time Bush friend and Miami lawyer Al Cardenas.
"We need your help," he wrote. "Perhaps we should meet with Secretary O'Neil and Secretary Evans, or whomever you think might be helpful. I have mentioned this case to Kelley McCullough from Karl Rove's office last December 8th when they visited Miami and have sent her briefings. Al Cardenas also knows of our need and has talk(sic) to some people."
The next morning, January 9, Bush replied
, "Jorge, I will see what I can do." A few hours later Bush forwarded the note to his chief of staff, saying only "for our discussion."
The initial request and Bush's response were not in the state's batch of emails provided to CNN or Bush's more limited release. The only indication of its possible existence is a publicly released email from that email chain where Rodriguez-Marquez thanked Bush the next day.
Bush emails obtained from the state in the following months show his top Tallahassee and Washington staff working consistently on the issue, including a renewed push in April 2002 and again, a few months later, when Bush sent a letter to James Rogan, then-director of the U.S. Patent and Trademark Office. Rogan, a former California congressman who helped lead the Clinton impeachment proceedings, was appointed to the position by Bush's brother, President George W. Bush.
The letter was not included in the emails released by Bush, but Christensen posted a copy he obtained.
"I am writing on behalf of Florida-based Bacardi-Martini USA, Inc. to ask that the Patent and Trademark Office take quick, decisive action on a pending application to expunge the registration of the trademark Havana Club. The out-dated registration belongs to a company owned by Fidel Castro called CubaExport and should be canceled immediately," Bush writes in the letter
Bush and Bacardi ultimately lost that battle -- and had it dragged out in public through much of 2002 and 2003 -- but the questions for Bush's campaign remain. Clinton's email troubles turned into the defining issue of her summer, sparking opposition in most polls and leading to deep concerns among Democratic donors.
The test for Bush will come if Democrats -- and maybe even some Republicans - begin unloading on him in the coming months for his missing emails.