Howard was born in 1869 in Boston, to a wealthy family - his paternal grandfather had made a fortune in Chinese opium smuggling. (I am related to his mother, not his father.) He had the usual elite Groton and Harvard education, but then went to Paris to study art under Benjamin Constant and Jean-Paul Laurens. I have found only one portrait of him - a phtograph of him posing with vine leaves in his hair, taken around 1885 when he would have been a teenager. It's in the Isabella Stewart Gardiner musem in Boston (I assume that she was a relative).
He came back, made a career of his art, and in 1903 married Ethel Emerson Cochrane, who was also from Boston (the ceremony was in Trinity Church). She is the subject of a lot of his best work.
Some of the paintings feature Ethel with a child. Going by the dates, it is probably their oldest, Olivia, who died in 1908 three months after her third birthday.
His portrait of his friend and patron Gertrude Vanderbilt Whitney was sold at auction a few years ago; the art world is coy about prices, but I see a note on one site that the reserve was $5000-$7000, and on another that it made 50% more than the reserve.
One evening in 1916, Ethel went out to Gertrude Vanderbilt Whitney's for the evening, Howard staying home because he had not been feeling well for several days. When she came home, Ethel slipped in quietly so as not to disturb him, and then found him dead in his bed in the morning. He was only 47, and their three surviving children were all under ten. Their house in New York, where they had lived since 1910, is still standing. The largest collection of his work is held at the Newport Art Museum in Rhode Island, which had a major exhibition about him last year.; the Cushings' holiday home, The Ledges, is near Newport (and still in the family).
As I mentioned, there were three surviving children. Ethel married again to a stockbroker; the older son, also Howard Gardiner Cushing, followed his stepfather and also became a stockbroker; the younger son, Alexander, was a lawyer who founded the Squaw Valley ski resort in California; and Lily followed her father and became an artist.
Here she is in 1939, admiring the newly acquired Picasso, Les Demoiselles d’Avignon, at the Museum of Modern Art on New York. She is the young woman on the left, partially concealed behind John Hay Whitney, then the Museum’s President; the older man next to them is a former Presdient of the museum, A. Conger Goodyear; pointing to the picture is another former President of the museum, and future Governor of New York and Vice-President of the United States, Nelson Rockefeller; the older woman with the hat is identified as Jeannie Sheppard; the other man is Edsel Ford, son of Henry Ford and head of the family firm; the woman on the right is art collector Elizabeth Bliss Parkinson.
We have another photograph of her in 1942, at the age of 33, taken by Horst P. Horst.
From the same year, a less flattering portrait by her friend Walt Kuhn:
And another photo by Toni Frissell with her daughters, dated 1960, but I think it must be from a few years earlier judging by the apparent ages - her daughters, both for the second of her three marriages, were born in 1933 and 1937; she's seated on the left and was born in 1909. The older daughter, another Lily, married Antony West, the son of Rebecca West and H.G. Wells; she died only last January. The younger daughter, Alexandra, married the historian Arthur Schlesinger.
Never mind other people's portrayals: here is her own self-portrait (date given is 1952, but that is surely wrong; she looks younger than 43).
She painted interesting if discreetly faint nudes:
Her clothed women are striking as well.
She was happy to go commercial: here's her 1949 portrait of opera singer Patrice Munsel for Avon Cosmetics:
Here's her extraordinary "Mrs Onassis".
And her landscapes and streetscapes are sort-of wistful.
Her papers are in the Archive of American Art.
Lily's middle name was Dulany, in honour of our mutual ancestor Walter Dulany (1723-1773) of Annapolis, Maryland, whose wife was a Delaware girl, Mary "Molly" Grafton (1727-1812); their home is now the US Naval Academy. The Cushings are descended through their oldest son, another Walter (1757-1807), and his only son Grafton (1794-1863) whose daughter Olivia (1839-1906) married Robert Maynard Cushing (1836-1907). (So Howard Gardiner Cushing lost his parents and his oldest child in quick succession.)
I'm descended from the older Walter's daughter Catherine "Kitty" (1764-1830); she married Horatio Sharp Belt (1746-1796), whose son Richard Grafton Belt, a homeopathic doctor (well dodgy) was the father of my great-great-grandmother Fanny. Any artistic genes were not really passed on to me, and quite likely came from elsewhere.
And just to add one more connection: William Temple Emmet, Lily's second husband and the father of her daughters, was descended from Thomas Addis Emmet and was also the grandfather of a good friend of mine, who I've known since 2008 without realising that we had a (weak) family link as well.