Lot 8105

ISAAC SHEFFIELD (Connecticut, 1798-1845), Sea captain at a window, circa 1840., Oil on wood panel, 25" x 20.5". Framed 31.5" x 27.5".

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ISAAC SHEFFIELD (Connecticut, 1798-1845), Sea captain at a window, circa 1840., Oil on wood panel, 25" x 20.5". Framed 31.5" x 27.5".

Estimate: $15,000 - $25,000

Starting Bid: $7,500

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by Eldred's
July 21, 2026 9:30 AM EDT
Live Auction
1483 Route 6A
PO Box 796
East Dennis, MA, US 02641

ISAAC SHEFFIELD
Connecticut, 1798-1845
Sea captain at a window, circa 1840.

The seated captain, resting his arm on the back of his chair, is wearing a gold lapel pin containing a ship portrait miniature, probably depicting his own vessel. Over his shoulder a green drape frames a busy whaling scene of a whaleship cutting in and trying out, a whale in a flurry, a whaleboat with six whalers wearing red shirts, and several other whales and ships in the distance. Housed in its original frame.

  • Provenance:
    Descended for several generations in the family of Mrs. Gertrude M. Minson, Uncasville, Connecticut, a descendant of Captain Gabriel Sistare (1725-1795) of New London. Minson surmised it depicts Sistare's grandson William M. Sistare (1794-1881) or an unknown area sea captain.
    Acquired from Gertrude M. Minson by Marguerite Riordan, Stonington, Connecticut, 1989.
    Acquired from Marguerite Riordan, November 15, 2004.
    The Collection of Nancy & Larry Dickson.

    Reference:
    "Isaac Sheffield, Connecticut Limner" by Edgar Mayhew, "The Magazine Antiques", November 1963, p. 589-591.

    Notes:
    Lot essay courtesy of Emily C. Esser, American Folk Art Specialist and webmaster of www.paintingsworthlookingat.com:

    Isaac Sheffield has long been a mystery. He may have been born in 1798, or maybe 1807; we know he died too young in 1845. Many portraits believed to be his work have been later proven otherwise. And Sheffield himself did not make matters easy. Among the small sampling of Sheffield's signed oil portraits, only four have a strong resemblance to the iconic sea captain template. One of those four trademark captains (Connecticut Sea Captain, National Gallery of Art, 1965.15.4) has a companion portrait, his wife, which instead resembles the work of Sheffield's fellow portraitist Orlando Hand Bears! And yet that Connecticut Captain himself is perfectly Sheffield's work. There can be no doubt: it bears the inscription "I. Sheffield Pinxt, April 1833.". Fortunately, the true Sheffield is nearly a dead-on stylistic match for the portrait offered here, Sea Captain at a Window.

    The confusion around Sheffield is very forgivable. It took me a long time to decipher it. But he is a very rewarding artist, once you get to know him. He had a consistently strong sense of color, painting in bright and hearty tones that make his work instantly distinguishable from his peers. Sea Captain at a Window especially benefits from the best of Sheffield's techniques. The pastel-toned sky, fading from blue to pink to gold, is a typical trademark. So is the unique style of curtain, rendered in vertical folds, with lines overlapping and cutting across diagonally. Sometimes, such as here, the curtain is green – an anomaly among folk painters, who spread the red curtain across all New England.

    A nearly identically formatted portrait is Captain Lorenzo Dow Baker, "posed in front of a whaling scene," as per the catalogue entry at Mystic Seaport Museum (cat. 1936.5). Likewise with our captain – a close look at the background scene reveals the defeat of the whale! Sheffield has cleverly included a narrative within the picture. The whaling captain Dow's name and biographical information have survived, telling us about his career verbally as well as visually. But we do not know Sea Captain at a Window's name. And the two works are so strikingly alike that it is tempting to speculate a connection.

    Then again, the similarity may simply be evidence of Sheffield's quality and consistency. A third example, Captain John Manwaring of New London, Connecticut (Christie's, January 20, 2023, Lot #467) follows the same format. He is accompanied by a female companion portrait of the captain's wife, Martha, both unmistakably by Sheffield's hand. He too, has a whaling scene in the window, almost identically executed, with a boat full of sailors towing away the unlucky behemoth. (Notably, Sheffield's earlier works, such as Connecticut Sea Captain, show the whale making his escape!)

    One unique and remarkable element in Sea Captain at a Window, not present in otherwise superb Sheffield pictures, is his lapel pin. Meticulously illustrated with a small image of a sailboat, the fine painting on the pin makes use of Sheffield's top talents as a miniaturist. In fact, Sea Captain has nearly everything one could ask for when looking for an ideal example of Isaac Sheffield's work. The captain's ruddy, slightly sun-burnt complexion is as full of life as the day he was painted.

    Isaac Sheffield's own life remains something of a mystery. His father was a shipmaster, and Sheffield's meticulously detailed, perfectly rendered ships suggest that he followed him into the career. Yet he is recorded only as a painter, who made his career in New York circa 1828-30 before returning to New London, Connecticut. Considering the quality of his rendering of faces and skin tones, it is likely Sheffield received some academic training, but not enough to erase his artistic individuality. Had he lived longer, we would likely have a larger body of work, and could know him better. As it stands, we must simply appreciate what we have.

    Signed examples and biographical reference:
    https://americanfolkportraits.miraheze.org/wiki/Category:Isaac_Sheffield
    Connecticut Sea Captain: https://www.nga.gov/artworks/50303-connecticut-sea-captain
    Captain Lorenzo Dow Baker: http://mobius.mysticseaport.org/detail.php?kv=110952&module=objects
    Captain John Manwaring & Martha Pool Manwaring: https://www.christies.com/lot/isaac-sheffield-1807-1845-a-pair-of-portraits-6410589/
  • Dimensions: Oil on wood panel, 25" x 20.5". Framed 31.5" x 27.5".
  • Condition: The absence of a condition report does not imply an object is free of defects. All items may have normal signs of age and wear commensurate with their age; these issues will likely not be mentioned in the condition report. Please contact Eldred's before the auction with any condition questions. Questions about condition will not be answered after purchase. Condition reports are provided as a courtesy, and we are not responsible for any errors or omissions. Important note on frames: Frames are not guaranteed to be in the same condition as they are in the item photograph. Due to handling and shipping, many frames, especially antique ones, are prone to losses. If you have questions about the condition of a frame, please contact us prior to the auction. 

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