If you have ever watched old pirate movies the word “skullduggery” conjures up visions of Long John Silver, Captain Hook, and Black Beard come to mind. The Webster’s Dictionary reinforces this stereotype with the noun definition of “underhanded or unscrupulous behavior, trickery.” Now that pirates have largely faded from history (except in Somalia) the term has taken on a broader usage to describe political, financial, or just underhanded activities.
Today a broader usage would include actions people believe to be deceitful, dishonest, or duplicitous. With politicians this would extend to bribery, graft, influence peddling, and other forms of illegal or undesirable behavior. We saw this recently in the discussion about Congressmen/Congresswomen and their profiteering from illegal insider information when buying stocks. Just as with pirates, this gives us an unfavorable opinion of the representatives and places them on par with the old-time pirates on the honesty scale.
We have seen this same skullduggery with the toppling of notable corporate figures like Bernie Madoff and Elizabeth Holmes. Generically it can be applied to the collective activity of companies like Enron.
Skullduggery was a solid descriptive term for the era of pirates, and unfortunately proper for our modern times when describing unfortunate issues and deceptive people. We need to bring back the usage of skullduggery because it is descriptive of things seen and experienced every day.

If you have never heard the non-word “misunderestimated” then you are just part of a crowd of people who missed a speech by President George W. Bush in Bentonville, Arkansas on November 6, 2000. President Bush used the sentence, “Oh no, they misunderestimate me.” in the speech.
President Bush’s confusing pronouncement came at the end of the campaign where he was locked in a battle with John McCain for the Republican nomination. It was that “just one more” speech that probably should not have taken place because it had no real impact on voters’ choices. Candidate Bush explained that his opponent and advisors had not simply “underestimated him, nor merely misunderstood him. Oh no, they misunderestimated me,”
Politicians are always under minute scrutiny, and none more than the Presidents of the United States. Every word is recorded, parsed, analyzed, twisted, interpreted, and sometimes just overanalyzed to the point of nausea. President Biden has had some notable gaffes and just outright confusing pronouncements, as do they all. In our minds the Bush gaffe ranks right up there with Vice President Dan Quayle who in June 1992 corrected the spelling of a young student to say that potato was spelled with an “e.” The “potatoe” incident stuck with him and killed any possibility of running for the Presidency.
In the world of double negatives, we assume by “misunderestimating” President Bush, they actually “overestimated” him.