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Although leaving the battle to save your friend might be contrary to military discipline in the 19th century, Shepherd was acting in the tradition of brothers in arms. Neither was regular army were they?

Good point, and good question. As I understand it, Touro was regular army, but Shepherd wasn't. My source for the anecdote is Walker's Jackson and New Orleans, as quoted in vol. 2 of Parton's Life of Andrew Jackson, pp. 165ff:

When the State was invaded, both [Touro and Shepherd] voluntered their services, and were enrolled among its defenders. Mr. Touro was attached to the regiment of Louisiana militia, and Mr. Shepherd to Captain Ogden's horse troop.

Soon after volunteering, Shepherd was appointed an aide to Commodore Patterson of the navy, and the task he dropped when he heard about Touro was the fetching of two masons to help in the building of a battery. So no, it isn't as if Shepherd was a sentry who deserted his post, or as if he left the front lines under fire. As a wealthy merchant like Shepherd, Touro could probably also have had himself put into a position of greater responsibility, but didn't, perhaps out of the same quirk of personality that drove him to man his New Orleans shop himself, twelve hours a day.

I guess I'm a bit surprised at the absence of a larger context here for NeverGotOverABrokenHeart syndrome. I think you forgot to mention just how frequently lifelong bachelors of the era gave that explanation.

And an explanation was a very important thing to have in that time. The social pressure to marry was much higher than modern readers can imagine, and likewise the social penalties for failing to do so were heavier than we can appreciate. Every "respectable" male member of society was either a devoted husband and father or had a good excuse, such as the death of a spouse, to account for the deficit. And men who were not "respectable" were at risk to keep their heads above water.

Today, no one would seriously entertain the NeverGotOverABrokenHeart ploy. Men (then and now) simply don't make their marriage decisions on that basis. But I don't think anyone alive today can tell us what proportion of the population was sentimental or naive enough to believe it then. A few naive women may have fallen for it. On the other hand, Touro's contemporaries deliberately printed the Doesn'tLikeCompanyOfWomen trope to quietly telegraph a significant message to their intended readership.

Touro's contemporaries would have understood the story in its unspoken context. Shepherd's success as a maritime merchant was utterly dependent upon his ability to accept his suppliers for precisely what they were: reckless, hard-drinking, whoring, and, in significant part, sexually bonded to one another.

Decades of research since Katz published Gay American History in 1976 have (at least in my mind) proven that Melville's suppressed hints of sodomy aboard sailing ships reflected a common situation. Therefore, Shepherd's best chance of winning the continued confidence of sea captains would have been if he were actually one of those comrades left behind with a kiss as the ship departs (see: "Calamus").

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