Late last month, former House Majority Leader Tom Delay (R-Texas), former New York City Mayor (and 2012 Republican presidential candidate) Rudy Giuliani (R) and conservative former U.S. Attorney Joseph diGenova hinted that, based on "sources" within and their experience with FBI, there is a substantial likelihood that Democratic presidential candidate Hillary Clinton Hillary Diane Rodham ClintonBarr criticizes DOJ in speech declaring all agency power 'is invested in the attorney general' Virginia Democrat blasts Trump's 'appalling' remark about COVID-19 deaths in 'blue states' The Hill's Campaign Report: Biden asks if public can trust vaccine from Trump ahead of Election Day | Oklahoma health officials raised red flags before Trump rally MORE will be indicted for mishandling classified information stemming from her tenure as secretary of State.

ADVERTISEMENT

Cognizant that federal investigations are highly secretive and that water cooler and barroom conversations by special agents working cases is extremely atypical, there are several issues regarding this latest Clinton scandal that beg consideration. The first is whether there is a legitimate chance that Clinton could be indicted. The second is a question of timing, as in, what happens if Clinton is indicted prior to the end of the Democratic primary or, if she becomes the Democratic nominee, prior to Inauguration Day should she win the presidency?

Since 1940, when President Franklin Roosevelt issued an executive order promulgating rules regarding classified military information, each subsequent president has issued similar orders that proscribe the penalties for failing to properly maintain classified information. In December 2009, President Obama issued Executive Order 13526; Clinton, serving as his secretary of State, acknowledged the rules governing the knowing or negligent mishandling of classified information by signing a non-disclosure agreement. Undaunted, Clinton allegedly used a private email account and home-brew server located in her New York state home to conduct official business while serving as secretary of State.

When news broke that Clinton may have disseminated classified emails, many of her supporters dismissed the issue as yet another Republican attempt to sully her tenure at the State Department. Clinton originally shrugged off the allegations as trivial, but the sheer volume of emails that were marked classified — numbering in excess of 1,300 — seems problematic.

Clinton's situation has drawn inevitable comparisons to another scandal, that of former Army Gen. and CIA Director David Petraeus. When news broke in 2012 that Petraeus provided classified information to his then-paramour, journalist Paula Boardwell, it was not until last year that the decorated general was indicted and pleaded guilty to one count of unlawful removal and retention of classified material — a misdemeanor offense. It is important to note that federal prosecutors initially considered levying felony charges against Petraeus that likely would have included prison time and a loss of his military pension, but outgoing Attorney General Eric Holder signed off on the misdemeanor, in part, to avoid a protracted and messy court battle.

Current Attorney General Loretta Lynch may have to decide, like her predecessor, whether the last months of the Obama administration should be spent embroiled in an unprecedented legal battle. America has withstood the impeachment proceedings of Presidents Andrew Johnson in 1868 and Bill Clinton in 1998, but never before has a major party candidate faced federal criminal prosecution. While it is clear that Clinton could be indicted, tried and potentially convicted while on the campaign trail, would a conviction for a misdemeanor offense be met with a pardon by an outgoing Obama? Such is practically impossible to predict, but an even more crucial question is if there is an open case, should Clinton win the presidency, would her newly appointed attorney general nix the case? The inherent conflict of interest would create a jurisprudence mess of gargantuan proportions.

Conventional wisdom would suggest that Lynch will likely kick the proverbial can down the road at least until the conclusion of the Democratic primary — if not beyond — but Giuliani, noting on the "Hannity" show in November that he used to prosecute alongside Lynch in New York, stated that "if the FBI recommends prosecution ... Lynch will indict."

What is interesting to note at this stage is that Clinton remains seemingly unfazed by the ongoing investigations. This marks a character concern that some Democratic and independent voters — not to mention the majority of Republicans — raise about her potential presidency.

Clinton, however, has been through political wars in Washington while serving as first lady and as secretary of State. Whether it was Travelgate, Whitewater or the Lewinsky scandal while first lady, the Clintons proved to be Teflon, with most charges refusing to stick or dim their political stars among the Democratic faithful. As secretary of State, Clinton seemingly outflanked congressional Republicans during the Benghazi proceedings in which she was grilled for what many consider her mishandling and lying about the terror attack on the American consulate in Libya that left Ambassador Chris Stevens and three other Americans dead in 2012. But with the Iowa caucuses looming, whether Clinton is ultimately charged or not will still force many Democratic voters to consider the "what if," as well as whether the potential benefits of another Clinton administration outweigh the ghosts of scandals past and present that seem to loom over the Clintons in perpetuity like the Sword of Damocles.

Hobbs lives in Tallahassee, Fla. and is an award-winning political commentator and trial lawyer who focuses on criminal defense cases in state and federal courts. Follow him on Twitter @RealChuckHobbs.