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Definitions

No, the specific words of the Second Amendment are not important. And yes, indulging the idea that they are is generally counterproductive. As thoroughly as this is explained in Lie #1, however, again the purpose of that and the related sections is not so much to convince as to eliminate the confusion that many will suffer after reading the quotes. In that spirit, below is the definitive answer to what the most controversial wording actually does mean.

Well Regulated
As surprisingly acknowledged by Stanford history professor Jack Rakove, a shameless “collective right” perpetrator,​
Well-regulated in the 18th century tended to be something like well-organized, well- armed, well-disciplined. It didn’t mean ‘regulation’ in the sense that we use it now, in that it’s not about the regulatory state…It means the militia was in an effective shape to fight.
Troops who had been regulated were thus known as “regular troops” or simply “regulars,” and while it’s tempting to cite some of the many quotes that illustrate this concept, in light of Rakove’s admission just one should suffice. According to an 1840 statement by Joseph Story, generally considered one of the greatest Supreme Court justices of all time,
[Though] the importance of a well regulated militia would seem so undeniable, it cannot be disguised, that among the American people there is a growing indifference to any system of militia discipline, and a strong disposition…to be rid of all regulations.
“Regulation” in the context of militia service, in other words, referred to the government forcing people to bear arms—not preventing them from doing so.
Militia
The classes of the militia are—

(1) the organized militia, which consists of the National Guard and the Naval Militia; and
(2) the unorganized militia, which consists of the members of the militia who are not
members of the National Guard or the Naval Militia.
This is the updated version of a 1792 act specifying that “every free able-bodied white male citizen of the respective States, resident therein, who is or shall be of age of eighteen years…shall severally and respectively be enrolled in the militia,” a concept reflected in the numerous quotes on this site which convey that “the militia” and “the people” are essentially interchangeable terms.
The People
The identity of “the People” was settled in 1990 when the Supreme Court ruled that
‘the people’ protected by the…First and Second Amendments…refers to a class of persons who are part of a national community or who have otherwise developed sufficient connection with this country to be considered part of that community.
Justices William J. Brennan Jr. and Thurgood Marshall, two of the most liberal of the last 50 years, went even further with a dissent which read in part,
Bestowing rights and delineating protected groups would have been inconsistent with the Drafters’ fundamental conception of a Bill of Rights as a limitation on the Government’s conduct with respect to all whom it seeks to govern. It is thus extremely unlikely that the Framers intended the narrow construction of the term ‘the people’ presented today by the majority.”
Brennan and Marshall never say their analysis doesn’t apply to Second Amendment, despite the majority opinion’s explicit reference to it—indicating that even as late as 1990, “collective right” lunacy had not fully sunk its parasitic hooks into the left.
Bear Arms
University of Baltimore law professor Kenneth Lasson expresses the typical “collective right” take on this phrase when he claims,
The right to ‘bear arms’ is aimed at a political end. It is a distinct military phrase having
political implications. A person in the pursuit of game or target shooting might carry his rifle, yet it would never be said that he had borne arms (p. 137).
Never. Never, ever, says the highly esteemed and totally honest professor. Strange, then, that a 1779 Virginia bill drafted by Thomas Jefferson and presented by James Madison mandates that one who violates hunting regulations will temporarily lose the ability to “bear a gun out of his inclosed ground, unless whilst performing military duty,” and that British naval officer John Cartwright stated in 1799, “To BEAR ARMS, means, 1st, to possess and use arms, whether it be as a professional soldier, or as a private citizen.” Several early state constitutions also contain the phrase “That the people have a right to bear arms for the defence of themselves and the state,” and a 1791 text even notes that “The orang-outang…knows how to bear arms, to attack his enemies with stones, and to defend himself with a club.”
More directly on point, the “Bear Arms” entry in the 1897 American and English Encyclopaedia
of Law reads,
This phrase, as used in the constitutional provision reserving to the people the right to
keep and ‘bear’ arms, has been held to include the right to load, shoot, and use arms as
such weapons are ordinarily used, and not to be confined to the simple right of carrying
arms upon the person.”
Last but not least, none other than Justice Ruth Bader Ginsburg wrote,

I would read the words [‘carries a firearm’] to indicate not merely keeping arms on one’s premises or in one’s vehicle, but bearing them in such manner as to be ready for use as a weapon…Surely a most familiar meaning is, as the Constitution's Second Amendment (‘keep and bear Arms’) and Black’s Law Dictionary indicate: ‘wear, bear, or carry…upon the person or in the clothing or in a pocket, for the purpose…of being armed and ready for offensive or defensive action in a case of conflict with another person.’

“A well regulated Militia, being necessary to the security of a free State”
Everything on this site essentially points to the fact that the Second Amendment could have read simply, “The right of the people to keep and bear arms shall not be infringed,” so knowledge of what the individual words mean still doesn’t tell us why the Founders attached the seemingly unnecessary clause responsible for so much national anguish over so many decades—but there is an identifiable answer.
​
While it’s commonly believed that the Founders planned for the country to rely almost entirely on state militias rather than a standing army for national defense, they were in fact quite conflicted about how practical this would be. As George Washington wrote back in 1776, for example,
To place any dependence on Militia, is, assuredly resting upon a broken staff. Men just
dragged from the tender scenes of domestick life…when opposed to Troops regularly
train’d, disciplined, and appointed, superior in knowledge and superior in Arms, makes
them timid, and ready to fly from their own shadows …The jealousies of a standing
army, and the evils to be apprehended from one, are remote; and in my judgment, situated and circumstanced as we are, not at all to be dreaded; but the consequence of wanting one…is certain, and inevitable ruin.
This why, in debate during the Constitutional Convention in 1787, George Mason
being sensible that an absolute prohibition of standing armies in time of peace might be unsafe, and wishing at the same time to insert something pointing out and guarding against the danger of them, moved to preface the clause (Art I sect. 8) ‘To provide for organizing, arming and disciplining the Militia &c’ with the words ‘And that the liberties of the people may be better secured against the danger of standing armies in time of peace.’
James Madison supported this suggestion because “as armies in time of peace are allowed on all hands to be an evil, it is well to discountenance them by the Constitution,” but Gouverneur Morris “opposed the motion as setting a dishonorable mark of distinction on the military class of Citizens” and it failed. The conundrum illustrated by this incident—how to acknowledge disfavor toward a standing army without smearing professional soldiers as representing “danger” or “evil”—provides the most plausible explanation for why Madison two years later introduced what became the Second Amendment as,
The right of the people to keep and bear arms shall not be infringed; a well armed and
well regulated militia being the best security of a free country: but no person religiously
scrupulous of bearing arms shall be compelled to render military service in person.
The final clause was removed because of concern that it could allow the government to “declare who are those religiously scrupulous, and prevent them from bearing arms,” and a motion to insert the words “‘for the common defence,’ next to the words ‘bear arms’” (p. 77) was likewise defeated. The Founders took pains to avoid verbal footholds that could be exploited by the inevitable history-twisting authoritarians of the future, but in trying to preserve a small nod to the advisability of constraining the size of the military, they failed.

A well regulated Militia, being necessary to the security of a free State, the right of the people to keep and bear Arms, shall not be infringed.”

According to Yale professor of constitutional law Akhil Reed Amar, a Democratic donor who has won numerous prestigious awards and been cited by Supreme Court justices in several dozen cases, the Second Amendment could be translated as, “An armed and militarily trained citizenry being conducive to freedom, the right of the electorate to organize itself militarily shall not be infringed.”

This conclusion is supported by—you guessed it!—quite a few historical quotes. Some of the statements below appear in other areas of this site, some don’t, but together they express two basic truths:

  1. Whatever reservations the Founders had about the effectiveness of the militia in actual combat against a foreign nation, there was no alternative to it for the deterrence of federal oppression. As for the applicability of this to modern times, speculation about the likelihood of success in defeating “tanks and planes” is completely irrelevant—no force can hold territory without ground troops, and a potentially tyrannical government must at the very least be forced to weigh the costs of its actions rather than simply do whatever it wants. 

  2. This deterrent was to be created by allowing the entire population to possess and train with arms, subject to reasonable state regulation. In the case of foreign or domestic aggression, the People could then assemble under the command of their respective state governors and militia officers as a “well-regulated militia” to either supplement or counter the professional military. Especially in regard to the latter scenario, it’s absurd to argue that the modern National Guard alone is sufficient—it is now part of the US Army Total Force, its members swear an oath to “obey the orders of the President,” and sections 252 and 253 of the Insurrection Act allow a president to deploy the military on US soil.

Thomas Jefferson, 1/26/1811

Resolutions of a New York City meeting headed by Henry Rutgers and Oliver Wolcott, Jr., 8/10/1814

William H. Seward, 2/11/1831

Supreme Court of Georgia, 7/1/1846

The Science of Government in Connection with American Institutions, 1866

An Introduction to the Constitutional Law of the United States, 1868

George L. Potter, 9/22/1875

Albert O. Wright, An Exposition of the Constitution of the United States, 1883

Rep. John H. Rogers (AR), 12/8/1890

Francis Newton Thorpe, 1894

Beecher’s Constitution and Civil Government of the United States, 1901

Lt. Col. James Parker, 8/1903

Horace Jewell Fenton, 1914

Pres. Woodrow Wilson, 12/7/1915

Lt. Col. Townsend Whelen on behalf of Secretary of War Dwight F. Davis, 2/6/1930

Asst. Secretary of War Frederick H. Payne, 3/4/1931

Rep. Wright Patman (TX), 8/13/1941

Maj. Gen. Lewis B. Hershey, editorial in The National Guardsman, the official publication of the National Guard Association, 7/1958

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