Did Dan Sickles Meet His Alter Ego in Eleanor Wilmerding?

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Daniel Sickles and Eleanor E. Wilmerding at the 50th Reunion Gettysburg
(LOC Public Domain)

A best estimate claims she was four years old when Dan Sickles shot Philip Barton Key in a “fit of insanity” (as he claimed during his trial). When Sickles disobeyed orders and lost his leg at Gettysburg she was eight. At the time of Sickles second marriage to Carolina/Carmina de Creagh {**} in 1871 Eleanor was sixteen and living in New York City with her father and two sisters.

As all things are in the life of Dan Sickles - - it’s complicated. Dan left his second wife in Paris along with his daughter and son in late 1879 to return to New York City. The couple never divorced as Sickles continued on with his life and at some point Eleanor Wilmderding appears as his housekeeper and companion. She was anywhere between thirty-six to thirty years younger than the Union general (depending on when you believe Dan Sickles was born as dates given are from 1819 to 1825).

There are various accounts regarding the arrival of Eleanor. Some place her being there when he returned back to New York in 1879 other dates have her arriving up to ten years later. Whatever her position in his house there are certain facts: she was dedicated to the general; she was possessive and jealous of his time with others; she was his constant companion; towards to end of his life she accepts more responsibility over his financial affairs; and to this day she is still a rather mysterious figure in the final chapter of General Dan Sickles’ life.

Eleanor proves to be an influential housekeeper

St. Patrick’s Day 1887: the day George Sickles the father of the former general died. George Sickles had accumulated quite a fortune throughout his days as a real estate developer, patent attorney and politician. In his first marriage he acquired his son Dan and in his second marriage he acquired a daughter Roma. At the time of his death Dan Sickles inherited $5 million dollars and becomes popular with those close to him.

Eleanor was safely ensconced in the Sickle home and trouble is coming to their doorstep via his wife and son. His daughter Eda Sickles Crackenthorpe had a tepid reconciliation with her father while his son Stanton was estranged from his father. Caroline came to the United States to try for a reconciliation. Of course this is after his inheritance so there is some question of her sincerity but in the end it will not matter for she meets Eleanor and Eleanor is not going to allow this woman into “her” home. When Caroline and Stanton arrive at the Sickle home this is how it’s been described:

“Imperiously Caroline had demanded Miss Wilmerding's dismissal With a last flash of his old gusty anger, the General had refused. And Caroline, barred from the house, had withdrawn to her suite at the St. Regis Hotel there to await the obviously imminent end. Stanton, bitterly critical of his father, had hastened overseas to reinforce his mother's claims- And with one stroke of the old paw, the General had laid him out dismissing him with battlefield peremptoriness and cutting his share in a mythical inheritance to one dollar!” {4}

Stanton told anyone and everyone “My father is completely in the clutches of this woman!” {2} Was it possible that Daniel Sickles finally find someone “just like him”?

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The 50th Reunion Gettysburg
(LOC Public Domain)

A Fool and His Money are soon Parted

General Sickles had problems with money. Sickles was a name familiar to the New York Press. In 1892 he was the chairman of the New York Monument Commission with a mission statement dedicated to erecting memorials at the Gettysburg and Chattanooga battlefields. Interestingly the newspaper article requested donations be sent to Sickle’s home directly which was located on Fifth Avenue and money began arriving, and then comes the questions. The books are not adding up and it smells fishy and investigation begins. When New York Controller William Sohmer finally saw the books on the commission there was approximately $28,000.00 in missing funds.

He was charged with embezzlement and was arrested. Once again Miss Wilmerding acted as his protector when she greeted the arresting officers:

[she] “screamed, "It's a lie!" The sheriff apologized. Friends followed him to jail, instantly bailed him out. On every corner the newsies were shouting, "The General arrested! General Sickles goes to jail!" {4}

But Sickles still had friends from both North and South came protests, telegrams and letters offering financial help. Even Helen Longstreet wrote a letter that was published in newspapers:

“My soul is sorrowed by your troubles. Am wiring the Attorney General of New York that I shall raise money among the ragged, destitute, maimed veterans who followed Lee to pay the amount demanded if the New York officials will allow sufficient time. We are writing into our history the story of degenerate descendants of heroic sires. The Republic, whose battles you fought, will not permit your degradation.” {2}

An embarrassed Sickles was removed from the position of chairman.​

The $5 million dollar inheritance from his father was long gone. It is estimated that $4 million was lost on Wall Street investments and the rest spent in extravagant gifts. He relied on his friends and rental income when he was forced to rent the top of his New York City home to make ends meet.

In 1913 when the 50th Anniversary of Gettysburg came along Sickles was now near or in his nineties. He was using a wheel chair at all times, was reportedly blind and his mental capacity was failing.

Eleanor lived with Sickles until her death in February 1914. As her casket was being removed from the Sickles home reports were broadcast that the general had died. After the death of Eleanor, Caroline was welcomed to stand by Sickles side. Filled with illness and loneliness she stayed with him until the end. In 1910 he met his grandson and namesake briefly when Stanton brought him to New York. He fell in love immediately with the boy he described as “a slender, breedy boy full of high spirits, spontaneous affection”. Before he died he penned a message:

“My dear Dan, your old grandpa is very ill; he would like to see you once more. I see big clouds in Europe. The Emperor Wilhelm n is a litde Bismarck. I predict war, a big war in tie near future, but I will not see it. Please ask your mother to send you over to see me.” {4}

He never saw his grandson again. On April 14, 1914 Dan Sickles suffered a cerebral hemorrhage. In his final hours he was surrounded by Caroline, Stanton, Mrs. Sickles’ attorney and a nurse. He passed away at 9:10 p.m. on May 3. Best estimates of his age at death: “six months shy of his ninety-fifth birthday”. {2}

Even in death he caused controversy as his wife Caroline pressured the Secretary of War that an exception be made to allow General Daniel Sickles to be buried near the New York Monument on the Gettysburg National Park. Her request was denied by Lindley Miller Garrison the Secretary of War.

After his death his son finally discovered the exact financial situation of his father. Despite having been gifted wealth from his father he was essentially bankrupt. The only real estate he owned with his New York home. When all was settled only $500.00 remained. His three war swords, his most prized possessions, were willed to Wilmerding and grandchildren. In 1915, Stanton Sickles began a court action to determine what happened to his father’s wealth yet nothing ever came from this. A safety deposit box in Eleanor’s name was discovered but when it was opened it proved to be just an empty box.

Even in death Daniel Sickles was going to go out of this life with style although not without creating a stir. The funeral was held at St. Patrick’s Cathedral on May 8. According to a friend who knew him well she declared that Sickles:

“would turn in his coffin with unholy indignation at having a Catholic funeral; but he had a most pretentious one”. {2}

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General Daniel Sickles leaving St. Patrick’s Cathedral
(LOC Public Domain)


The Catholic service was Caroline’s wishes.
Perhaps revenge is a dish best served cold.


* * *



Sources
1. http://daytoninmanhattan.blogspot.com/2020/04/the-lost-daniel-e-sickles-house-23.htm
2. “Sickles at Gettysburg” by James A. Hessler
3.
https://www.findagrave.com/memorial/2113/daniel-edgar-sickles
4. https://archive.org/stream/dansickles006872mbp/dansickles006872mbp_djvu.txt
{**Note: Dan Sickles’ second wife’s Spanish name is Carmina americanized to Caroline as I have seen in some sources and use in this thread.}
 
Great post. Thanks.

Sickles
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always leaves me shaking my head ... usually speechless.

The best I can do at the moment is to paraphrase Hamlet: "What a piece of work is Dan!" [But, if you don't mind, I'll leave out the part that says "In action how like an angel, in apprehension how like a god!"]
 
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What was Daniel Sickles personality like, does anyone happen to know?

Trouble and bad press seemed to always follow him. So I would wager if I knew him on a personal level (not serving under his command) I would try to avoid him. Regardless of how nice of a guy he possibly was.
Well, within 3 days of his wounding at Gettysburg he was already giving an interview if that tells you anything.
 
What was Daniel Sickles personality like, does anyone happen to know?

Trouble and bad press seemed to always follow him. So I would wager if I knew him on a personal level (not serving under his command) I would try to avoid him. Regardless of how nice of a guy he possibly was.

I don't know if he's ever been described as nice? I mean, he wasn't. That the bad press managed to leak around the edges of his own, manufactured terrific press tells you a lot. If ever anyone tried to live up to a nickname it was Dirty Dan and the trouble was already there- no need to follow the guy.
 
I don't know if he's ever been described as nice? I mean, he wasn't. That the bad press managed to leak around the edges of his own, manufactured terrific press tells you a lot. If ever anyone tried to live up to a nickname it was Dirty Dan and the trouble was already there- no need to follow the guy.
Thank you for the post. Very informative article! I am glad I don’t have his stock broker!
 
Back in those days, the husband usually got the benefit of the doubt in cases of marital infidelity. Even though his wife Teresa was engaged in an affair with Philip Barton Key (yes, that Key, the son of Francis Scott), Sickles' own philandering was overlooked. He was in fact criticized for "forgiving" Teresa after he was acquitted on the charge of murdering Philip.
 
Definitely, an interesting character. A few years back, I had a discussion with a Sickles reenactor/living historian. He stayed in character most of the time. According to him, Dan could do no wrong. His vitriol against Meade and Scott Key seemed so real, I wouldn't have been shocked if he was missing a leg. I, unfortunately, did not ask him about Eleanor W. I'm sure he would have had theories about her.
 
One of the more "unusual" representations of Dan is this mannikin in the Gettysburg Diorama And History Center on Steinwehr Ave.

How have I missed that? It's a little terrifying, isn't it? The thing is, if it hadn't been for Dan we wouldn't have the battlefield as we know it, would we? Didn't he save it from being carved up into a mere tourist attraction? If you have to have a saving grace, that'd be an awfully good one.
 
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