Hillary vs. Jeb: In Their Own Words (and Inboxes)

Posted By on Jan 29, 2016

The 2016 presidential race has given us Trump, Bernie, and most excitingly (if you’re an email geek) a plethora of emails to and from Hillary Clinton and Jeb Bush. The State Department has published scans of thousands of pages of Hillary’s emails from a private server she used during her tenure as Secretary of State. Jeb Bush, meanwhile, self-released over 280,000 emails from his time as Florida Governor on jebemails.com

While some may be sick and tired of hearing about these damn emails, they can help us understand the behaviors, attitudes, and leadership styles of the two fundraising leaders in the 2016 election. What can we learn from the emails of these two candidates vying for that president@whitehouse.gov email address?

Women of Power: Hillary, Jeb (you’ll see), and their Inner Circles

First, let’s look at who Jeb and Hillary relied on during their political service by seeing who they emailed most often.


jeb-bush-closest-advisorsDespite a typically male-dominated political environment, women make up all of Jeb’s top five most contacted recipients, each receiving over 900 emails from Jeb while he was governor.  Jeb hinted that he’d pick a woman for VP, announced that he loved his mother more than his dad, and clearly has no qualms with working with women at a high-level.

For those cynical he’d pick a female VP just to curry political points, his inbox doesn’t lie: he’s been relying on the counsel and political skills of women in government for years. Jeb’s pro-life, Republican values may hurt him among women in a general election, but Republican women support him 20% more than their male counterparts, and he may seek to grow this base further as he tries to break the spells of Trump and Cruz.

Despite receiving thousands of emails, Jeb’s top five recipients made up just 7% of his email volume. Jeb sent emails to thousands of individuals: colleagues, staffers, and everyday citizens, even replying to requests for his autograph.

He claims to have spent 30 hours a week checking email when governor (which, sad to say, may now be average), and the thousands of contacts and messages in his released email folders give credibility to his claim. A Hillary presidency would be a grand, historic day, though if the 2016 race came down to her and Jeb, it’s likely that we’d see a more gender-balanced cabinet than with Obama or presidents past either way.

So who were these top recipients? Bunny Hanley (Director of Citizen Services) was the point of contact for Terri Schiavo related emails, giving her the honor of the person Jeb emailed most, as he forwarded along hundreds of these emails to her. Patricia Levesque (Deputy Chief of Staff), Raquel Rodriguez (General Counsel), Celeste Lewis (moved between Director of Appointments and Director of Citizen Services), and Pamella Dana (Director, Office of Tourism, Trade, and Economic Development) round out Jeb’s other most frequent recipients.

Celeste Lewis was among Jeb’s staffers who Florida Speaker of the House Marco Rubio (perhaps a familiar name) poached for his staff when Jeb left the governorship. Interestingly, Lewis appears to have donated only to Jeb’s campaign, despite most recently working for Rubio. (Bob Ward, Rubio’s Chief of Staff at the same time Celeste worked for the then-Speaker, also only donated to Jeb Bush’s SuperPAC.)



What about Hillary? Her top three recipients (by email volume) are predictable: chief of staff Cheryl Mills and deputy chiefs of staff Jake Sullivan (who is seen as a frontrunner for National Security Advisor in a Clinton administration) and Huma Abedin.

Nearly half (43%) of the emails Hillary sent went to these three close advisors. Hillary’s account was kept secret from the public and many at State, which explains why just four contacts received the majority of the emails she sent, in stark contrast to Jeb, whose top fifty recipients received 18% of his emails.

The rest of the top ten is composed of Hillary’s special assistants or others that worked at State, with the exception of Sidney Blumenthal. The Obama Administration disallowed Blumenthal, a former Clinton aide, activist, and journalist, from being hired by the State Department because of his role in spreading attacks on Obama during the 2008 primaries. Despite this, he was still a top ten recipient (and frequent sender) of Hillary’s private server emails, and clearly worked to maintain as much of his influence as he could behind the scenes.

The Candidate’s Most Demanding Weeks (in Email Volume)

Hectic Times for Hillary

Hillary’s busiest week as Secretary of State (based on incoming and outgoing email volume) was during the aftermath of the Benghazi attacks, even in her unclassified inbox. Other international crises correlated with upticks in email volume, such as the start of the Libyan Civil War and the 2010 Haiti Earthquake aftermath.


The second busiest week, in August 2010, did not appear to be caused by any international incident. However, this week saw a front-page Washington Post article criticize US-Pakistan ties, resulting in a lengthy email chain involving Hillary and Raj Shah (the head of USAID).  Hillary sent multiple emails this same week regarding drafts of a piece she was penning for the Foreign Affairs titled  “Leading Through Civilian Power”. Hillary’s focus on the media highlights the influence it has even on non-elected cabinet members. (To further drive this point home, the fifth busiest week corresponded to diplomatic protocols drafted between Turkey and Armenia, but attempts at establishing an interview with Oprah the same week generated nearly as many emails.)

Serious Situations in the Sunshine State

Jeb’s political portfolio, and thus also his emails, were focused on Florida issues and events. In March 2005, arguments over Floridian Terri Schiavo’s “right to die” become a national news story, and Jeb saw an all-time high 7,800 emails in a week go through his mailbox, mostly from pro-life advocates who asked him to do what he could to stop her from passing. Her fate was ultimately decided by the courts, but Jeb Bush tried his best (including ordering the reinsertion of her feeding tube) to advocate the pro-life cause. A decade later, the issue is as polarizing as ever: Jeb’s SuperPAC spawned controversy just this week by championing his response to Terri Schiavo in an attempt to win over conservative South Carolina voters.


Jeb’s second busiest week was toward the end of 2005, when he instead caught the ire of the religious right. The Florida Family Association organized a write-in campaign urging Jeb to divest Florida’s retirement fund from a video rental company whose offerings included adult films.  Jeb does not appear to have responded directly to any of these emails, instead forwarding them along to Coleman Stipanovich, head of the state’s fund. (Florida did divest from this stock in 2006.)

Other peaks in email volume resulted from citizen support and opposition to specific Florida bills:

  • HB 1911 was a Florida House bill that allowed motorcyclists to not wear helmets. Bikers overwhelmingly wrote in to support the bill.
  • HB 253 was a Florida House bill that allocated tobacco settlement funds toward biomedical research. Many elderly citizens (or those worried for elderly citizens) wrote in asking him to stop the bill/veto it, fearing it would take funds away from their own programs.
  • SB 540 was a Florida Senate bill that relaxed restrictions on boating which had been in place to protect manatees. Many Floridians, conservationists, and environmentalists wrote in asking him to veto the bill.

Jeb called himself “Veto Corleone”, but he did not go against his Republican-controlled legislature and signed all three bills, including the two with significant opposition in his inbox.

Pls and Thanks: Diving into the Diction of Jeb and Hillary

Click to explore the word cloud.

Hillary on her Blackberry spawned a meme, and while she used shorthand in emails akin to texting, she clearly still preferred a hard copy when reading an article or document. Her emails often involved requests for someone to print documents and emails (“Pls print”), set up calls (“Can you call me”), or brief her on a given topic (“Let’s discuss”).

As the word clouds  suggest, Hillary took an imperative tone of voice more than Jeb, with 18.3% of her sentences being request or command-like, compared to 13% for Jeb. Even Donald Trump has called Jeb a “gentleman”, and Jeb’s emails include unsolicited, out-of-the-blue compliments to staffers and others. Hillary’s emails often start with a “pls” or end with a “thx”, but she is more to-the-point and succinct. Because Hillary’s private email account was kept on the down low, she had few formal or official emails in it, and her emails were largely to and from just her staffers and trusted advisors.  

Click to explore the word cloud.

Jeb also frequently emailed his staff, but such messages are outnumbered by thousands of emails between him and Floridians at-large. Jeb strikes a polite and formal tone in all of these exchanges, even to emails that cursed him out, often thanking the writer for their input or advice. Jeb regularly played the role of listener in his emails (“I appreciate your advice”/”Your input is greatly appreciated”), thanking citizens for their concerns (“Thank you/Thanks for writing”), in contrast to Hillary’s more delegating-heavy emails.

Both Jeb and Hillary kept their messages brief. The median word counts for Hillary and Jeb were nine and ten words, respectively. 99% of Hillary’s emails were 89 words or less, and 5% of had no message in the body, only a subject line. Her most common email length was just two words.  Likewise, 99% of Jeb’s emails were 114 words or less, with 1% involving a subject-only message.

Final Thoughts (TL;DR)

  • Both a President Hillary or a President Jeb would probably have a strong gender-balance in their leadership and advisor teams.
  • The busiest days of email in Jeb and Hillary’s tenures in office corresponded to major events (Terri Schiavo and Benghazi) that are still talking points in their 2016 campaigns.
  • Jeb’s self-proclaimed title of being the eGovernor seems rather fair based on the tens thousands of emails he sent during his term. Even if he’s still figuring out the Apple Watch.
  • Hillary and her staffers would save a lot of time and emails if they just got wireless printing setup.
  • You’ll never see Jeb in a speedo!

    We never thought we’d upload a file called jeb-in-a-speedo.png



  1. Extremely well researched and crafted. A perfect ratio of text to infographics, as well.

  2. Wow what a great article

  3. That was serious dedication to understanding email habits/use. Did you create personas from this work?

  4. We didn’t have a chance to do that, but it’d be a fun idea!


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