During the Captiva Island Historical Society’s recent Creativity & the Art of History program, one painting emerged as an especially powerful moment of connection between art, history, and lived experience.

The painting, She’s a Lady, created by Captiva resident—artist and author—Ilie Ruby, drew special attention from Ralph Woodring. The work honors his mother, Esperanza Woodring, and her place in the colorful fishing history of both Sanibel and Captiva Islands.

"She's a Lady" - Ilie Ruby's painting featuring Esperanza Woodring 

CIHS board members and artist Ilie Ruby with the painting the CIHS purchased to gift to Ralph Woodring  (from the left: Tom Libonate, Brian Holoway, Ms. Ruby, Mary Jane Vinson, Mike Boris)

The title of the painting reflects a story shared during the program by CIHS board director Brian Holaway, who spoke of interviewing fishing guides over the years. Often, after naming the men who worked the waters, they would pause and add, “There’s one more… and she’s a lady.”

That lady was Esperanza Woodring—a respected guide whose skill, determination, and presence left a lasting impression on those who knew her.

The CIHS presents the painting featuring his mother to Ralph Woodring

In a deeply moving moment, the Captiva Island Historical Society surprised Ralph Woodring by acquiring the painting and presenting it to him in recognition of the Woodring family’s deep roots and enduring contributions to island history. Visibly touched, Ralph then offered a gift of his own to the audience, sharing personal memories of his mother that brought her story vividly to life—her work on the water, her strength of character, and the example she set for generations to come.

The original image that inspired Ilie Ruby's painting of Esperanza Woodring

The moment served as a poignant reminder of how art can illuminate history, honor those who shaped it, and create powerful connections between past and present.