First Lady Biography: Frances Cleveland

FRANCES CLARA FOLSOM CLEVELAND [PRESTON]

Although Frances Folsom Cleveland was the wife of President Grover Cleveland and served as his First Lady for part of his first term and during all of his second term, he entered the presidency as a bachelor. His unmarried sister Rose Elizabeth Cleveland served as the first First Lady of the Cleveland Administration, until his June 1886 marriage to Frances Folsom. The biography of Rose Elizabeth Cleveland follows at the conclusion of the Frances Cleveland biography.

Born:   

Buffalo, New York

21 July, 1864

Father:

Oscar Folsom, born 8 November, 1837 in Cowlesville, New York, lawyer; died in carriage accident on 23 July, 1873.

Upon Folsom's death, his close friend and law partner Grover Cleveland became executor of his quarter-million dollar estate; he did not become the legal guardian of his future wife Frances Folsom Cleveland as has been widely believed.

Mother:

Sixteen years after the death of her first husband, Emma Folsom married Henry Edward Perrine on 20 May, 1889.

Stepfather:

Henry Edward Perrine, born 20 March 1827 in Sodus, Wayne County, New York; died 30 May, 1901 in Buffalo, Erie County, New York.

Ancestry:

English; all of Frances Cleveland's ancestors were from England and settled in what would become Massachusetts, Rhode Island and New Hampshire, eventually migrating to western New York.

Following her father’s death when she was nine years old, Frances Cleveland’s only nuclear family member was her mother. However, both mother and daughter were tightly bound to Emma Folsom’s family and in that sense, the future First Lady was raised among many other children. During her high school years, Frances lived with her grandmother in Medina, New York.

Remarkably, her two grandmothers were alive at the time she became First Lady, upon marrying President Cleveland on June 2, 1886. It is not clear whether her maternal grandmother Ruth Rogers Harmon attended the Folsom-Cleveland wedding in the White House. Frances Cleveland’s paternal grandfather John Folsom, who was originally intended to preside over her wedding ceremony died just 16 days before the marriage date.

Birth Order and Siblings:

One sister; Nellie Augusta Folsom (18 December, 1871 - 7 February, 1872)

Physical Appearance:

Taller than 5' 7" in height, black hair, dark blue eyes

Religious Affiliation:

Presbyterian

Education:

Madame Brecker's French Kindergarten, 1870-1871, Buffalo, New York

Miss Bissell's School for Young Ladies[grammar school] 1872-?

Medina Academy for Boys and Girls,Medina, New York, ? – 1879

Central [High] School, Buffalo, New York, 1879-1881: perhaps depressed over a broken engagement, she dropped out of her senior year but secured completion of her course of study through certification.

Wells College, Aurora, New York, 1882-1885 : she successfully passed exams in Latin and German to gain entrance in the winter semester at one of the first U.S. liberal arts colleges for women, she developed her avocation for photography at this time but also studied academic subjects that further included botany, astronomy, logic, religious studies, and she especially enjoyed political science. She was active in the theater club, building sets, sewing costumes and acting. She was also a member of the Phoenix Society, a debating club, once delivering a complicated speech on free trade, the tariff and protectionism.

Occupation before Marriage:

Since she had but one year between graduating from college and marrying the President, Frances Folsom had little time or wherewithal to pursue any personal interests or goals; she did visit seven European nations with her mother on a nine month exploration, from September 1885 to May 1886, as arranged by the White House.

The President had proposed to Frances Folsom in the spring of 1885 during a visit she and her mother made to Washington. Emma Folsom was not initially pleased with the engagement, believing that it was she and not her daughter to whom Cleveland might have proposed marriage. The President wanted Frances Folsom to tour Europe and understand the continent's more formal social customs and protocol, as well as visit historic sites and her family wanted her to assemble an appropriate trousseau for the public appearances she would immediately be asked to make as First Lady.

Marriage:

21 years old to [Stephen] Grover Cleveland (born 18 March 1837, Caldwell, New Jersey, died 24 June, 1908, Princeton, New Jersey), President of the United States, on June 2, 1886 in the Blue Room of the White House.

After a honeymoon in a private cabin at Deer Park Lodge in the Catoctin Mountains of Maryland, they returned to their home, the White House.

Although he did not anticipate the degree to which the press would intrude on his private life with his new bride, President Cleveland foresaw that the public interest in “Frank,” as she was known to those closest to her, would be great and possibly an oppressive burden for them both. In seeking to prevent this as much as was possible, he purchased a 27 acre working farm in the Georgetown Heights section of Washington, later to be called "Cleveland Park." The house afforded the privacy he wished to ensure for him and his new bride and they only lived at the White House during the active social season, from November to December and then from February to April. The house was called "Oak View" by the First Lady but always known as "Red Top" because the roof was painted red. The Clevelands sold the property at a considerable profit when they left Washington in 1889.

When they returned to Washington for the second Cleveland term in 1893, they rented a home called "Woodley."

*FrancesFolsom Clevelandis the youngest presidential wife to become First Lady

*FrancesFolsom Clevelandis the only First Lady who was married in the White House

Children:  Three daughters, two sons; Ruth Cleveland (3 October, 1891 – 7 January 1904); Esther Cleveland Bosanquet (9 September, 1893 – 26 June, 1980); Marion Cleveland Dell Amen (7 July 1895 -18 June 1977); Richard Folsom “Dick” Cleveland (28 October 1897 – 10 January 1947); Francis Grover Cleveland (18 July 1903 – 1995)

*In 1921, the Curtis Candy Company supposedly honored Ruth Cleveland by naming one of its candy bars "Baby Ruth" in her honor.

**Esther Cleveland is the only child of a President who was born in the White House.

Occupation after Marriage:

Like Julia Tyler and Edith Wilson, marriage to an incumbent President meant for Frances Cleveland that she immediately became First Lady, with very little time to consider with any depth what type of role she would play. Considering the fact that her husband was not only almost three decades older than her but had already served as assistant District Attorney and then Sheriff of Erie County, New York, Mayor of Buffalo and Governor of New York, it was President Cleveland and not his wife who largely dictated what she could and could not do as First Lady, with a sense of political consequence. Before she married him, Cleveland had already given conscious thought to how to divide her life between public and private responsibilities.

First Lady

21 years old

2 June, 1886 - 4 March, 1889 (remainder of first term)

The historic wedding of the only President and First Lady to wed in the White House attracted enormous international attention in the week and days leading up to the event, once it was learned that the President was not marrying his widow friend Emma Folsom but rather her 21 year old daughter. Reporters stalked every move of the bride as she made her way from New York to Washington, D.C. There were newspapers several newspaper stories every day on some aspect of the wedding, from a glimpse into the factory where the wedding cake boxes were being made to the types of gifts that were pouring in. On the day of the wedding, crowds gathered outside the mansion and could hear the strains of music played by John Philip Sousa who led the Marine Band. The entire house was festooned in flowers and the bride even wore a train trailed in orange blossoms. The guest list was limited to family, close friends, plus cabinet officers and their wives. Journalists were barred from the wedding (except for a last minute glimpse at the floral displays), and participants refused interviews. After the ceremony had ended, the entire city erupted with church bells pealing, ships blowing their horns and some well-wishers ringing hand bells.

Despite the President's best efforts "Frankie" (as she was called in the popular press, a nickname she disliked) became an instant celebrity. She was so mobbed by admirers at public events that the president feared for her safety.

The new First Lady joined the President in an unprecedented tour of the South and West in 1887, and it only increased her fame and popularity. In St. Louis souvenir coins were even struck to commemorate her visit there. The weekly illustrated newspapers,Harper's and Leslie's made her a frequent cover girl, using her as a drawn illustration in the most mundane of activities - and always sold more copies.

Young women copied her unique hairstyle (which called for all long strands at the neckline to be cut round) and even the poses she took in her formal photographs that were released to the press.

So closely was her clothing style copied that during the summer of 1887, when two Washington reporters found themselves with no general interest stories, they created a tale that the First Lady had decided to stop wearing the bustle-type dress: shortly thereafter the popular bustle met its fashion demise across the country.

The Women's Christian Temperance Union, alarmed that the young First Lady wore gowns that bared her shoulders petitioned her to stop wearing such clothing because it was an evil influence on young American girls. She neither responded nor stopped wearing low-cut gowns; the WCTU nevertheless distributed fliers at its convention saying she had. Businessmen quickly realized the marketing potential of the young, pretty, and vivacious first lady.

Through the evolving technology of both photography and the reproduction of it in newspapers and magazines during the Cleveland era, not only the entire American nation but the world knew how young and attractive the new First Lady looked in real life.

Immediately after her wedding, the facial image of Mrs. Cleveland began appearing publicly for sale on a wide range of items. These fell into several types of categories. There were products such as ceramic tiles, sheet music, silver pill boxes, sewing kits, cigar boxes, candy, women’s perfume and even a tobacco pipe, which simply appropriated her image to adorn the objects being sold.

More commercial but not entirely exploitive were the “trade cards” of the era; these were small cards that all ranges of business and stores used to advertise their goods, and which usually carried some pleasant scenic image and the name and address of the store below it. In this form, Frances Cleveland’s face appeared on calendars, ashtrays, and greeting cards for small businesses. These items were given away for free to customers as a form of advertising.

The most offensive of the commercial merchandizing of the First Lady, however, were those businesses which used her as an implicit point of their advertising, making no effort to mask the claim that Mrs. Cleveland owned, bought or used their items. Many of these advertisements did not simply use her facial image to suggest that she had endorsed their items but incorporated her into scenarios which depicted her enjoying them. In this category, Frances Cleveland was shown picking out fabrics, using a new sewing machine, being led to her new piano,

The problem became so widespread that one Democratic Congressman attempted to pass a bill in Congress that would halt the use of any woman's image - whether she be private citizen or celebrity - for commercial purposes without her written permission. When the bill failed to even come up for a vote in the House, the floodgates seemed to open wider in regard to the exploitation of "Frankie" Cleveland.

Frances Cleveland finally sought to consciously use her influence in ways that she considered more uplifting for her countrywomen. Perhaps the most pronounced and somewhat surprising were the receptions that she began to host on Saturday mornings, held especially for those working-class women who were unable to visit the White House during the weekdays. Some White House domestic staff members, such as Ike Hoover, were shocked as "common" shopgirls, government clerks, maids and other service industry workers lined up in the regal East Room to shake the hand and have a personal word with the popular young First Lady. When she attended a ceremony to mark the opening of an organization that provided for educational, social, and practical opportunities for factory workers and made a point of greeting women workers, it made the cover of the November 1887Harper's Weeklymagazine.

While she was not an activist for temperance like Rose Cleveland - who initiated a ban on hard liquor being served in the White House during her fifteen months as hostess - Frances Cleveland set a personal example regarding drinking that she hoped other American women would follow: she permitted the serving of alcohol at events during which she was hostess, but turned down her own wine glasses at White House state dinners and drank only Apollonaris sparkling water.

Frances Cleveland also made a concerted effort to support the fledgling careers of young women musicians in an era when the professional field of those who were offered the most lucrative and extensive performance contracts was limited almost exclusively to men. She sponsored a young violinist to study in Berlin and the girl became the first American to win the prized Mendelssohn Stipendium.

Frances Cleveland also lent her support to both national and local Washington organization that were headed by women such as the WCTU's "Hope and Help" project. She immediately agreed to help a Washington African-American woman to establish The Washington Home for Friendless Colored Girls after she had come across two starving girls eating out of a garbage can and then raise funds to purchase a building for the orphanage. She was also the most visible member of the Colored Christmas Club, a charity providing food and clothing to poor local children at the holiday season. A year after her marriage, she also accepted a position on the board of trustees for Wells College, her alma mater. Believing strongly that a woman should be provided with a higher education, Frances Cleveland also aided individual women in pursing a college degree and professional employment, and maintaining a network of like-minded women by helping to found the University Women's Club. She was later instrumental in urging the State of New Jersey to "open up educational opportunities for girls, like young men," resulting in the founding of the New Jersey College for Women.

To handle the large amount of correspondence she received, perhaps more than any of her predecessors, she hired a college friend, Minnie Alexander to serve as her social secretary, the first non-family member to fill such a position for a First Lady. It was not yet, however, a government job and so the Clevelands paid Alexander's salary themselves. Frances Cleveland and Minnie Alexander set about creating some efficiency in dealing with the deluge, creating the first set of form letters to respond to the various needs and requests the First Lady received.

As a hostess, Frances Cleveland followed a more traditional manner; in fact, she took direct instructions from one of her predecessors, Harriet Lane Johnston, the niece and hostess to the last Democratic president to have been elected, bachelor James Buchanan. A Washington resident, Harriet Lane was a frequent guest at the White House and befriended Frances Cleveland. During her tour of the South with the President, Frances Cleveland also met with her elderly predecessor Sarah Polk at her Nashville, Tennessee estate, "Polk Place."

President Cleveland believed firmly that "a woman should not bother her head about political parties and public questions," and Frances Cleveland followed this sensibility by refraining from either learning the details of the issues he faced or the Administration agenda. Nevertheless, simply by the virtue of her popularity, Frances Cleveland was highly useful to her husband as a symbol of his Administration. On one occasion, in the midst of his 188 re-election campaign, she did make a highly heralded trip to the Capitol and preside from the visitors' gallery over a special session of Congress that the President had called to enact his proposal for a lower tariff. The Democratic National Committee, with the President's permission, also drew on her popularity for its own purposes. They inserted a pamphlet called, "Bride of the White House" into the literature it distributed to the party faithful as well as the politically undecided.

Presidential Campaign and Inauguration:

Frances Folsom Cleveland did not participate in the 1884 election of her future husband; she did not attend the 1885 Inauguration because she could not get permission to take leave time as she completed her last year at Wells College.

Cleveland 's political enemies spread rumors about his wife in order to discredit him. A Republican after-dinner speaker gave credence to the fiction that Frances Cleveland was having an affair with newspaper editor Henry Watterson (the two had simply attended the theater together).

Just before the 1888 Democratic National Convention, Democratic opponents of Cleveland published accusations that the president beat his wife and mother-in-law. Frances Cleveland was forced into the unique position of issuing formal statement denying the allegation, and praising her husband's tenderness and affection. Her mother dismissed the charge as "a foolish campaign ploy without a shadow of foundation."

At the Democratic National Convention, the First Lady was mentioned by name from the podium by the chairman, thus making her the first presidential wife to be so recognized in a political arena. Against the President's wishes, Frances Folsom Cleveland's image appeared on numerous campaign paraphernalia, such as flags, posters, handbills, plates, ribbons, handkerchiefs, napkins, and playing cards. One poster even placed her portrait between that of her husband and his running mate, Allen Thurman. The pervasive merchandising of Mrs. Cleveland was unprecedented. In response, the Republicans placed Caroline Harrison's picture on posters. Although they could not vote, women were very active in campaigns, and in 1888, Democratic women across the country organized themselves into Frances Cleveland Influence Clubs.

Mrs. Cleveland was not featured much in the 1892 campaign, but she remained a very popular focus of press and public attention.

First Lady (second, non-consecutive term)

4 March 1893 - 4 March 1897

28 years old

Becoming the only former First Lady to return to the position four years later, Frances Cleveland was a different woman in 1893 from the bride who had assumed the role in 1886. Her most immediate priority and responsibility would prove to be her three small daughters, two of whom were born during Cleveland's second term. Unwittingly, Frances Cleveland had helped to change the public image of Grover Cleveland from the coarse Buffalo politician who had taken responsibility for fathering an illegitimate son and enjoyed drinking beer into a devoted husband and doting father to toddler daughters.

The second Cleveland term, however, was shadowed by the economic depression of his immediate first year (1893). Widespread unemployment and dissatisfaction with Cleveland's response to it led not only to tense and fearful clashes between unemployed men and authorities throughout the country but a radical change in the life of the First Lady and her family. There was a sharp increase in the death threats made to the President, and Frances Cleveland - without knowledge or permission of her husband - had Secret Service protection of him and of the White House increased. At the Clevelands' summer home in Buzzard's Bay, the First Lady was alarmed when several suspicious men refused to leave the property and feared that they posed a kidnapping threat to her baby daughters; she finally had to call in the Secret Service.

During the economic depression but while he and his family were at the summer home, Grover Cleveland was diagnosed with jaw cancer and it required immediate surgery. The Clevelands believed that a public disclosure of the President's condition would add to the sense of national instability, the surgery was secretly performed at sea. Frances Cleveland played a large part in the successful deception of the press and public, specifically misleading those who questioned the whereabouts of the President or the true reason for his lengthy absence from any public appearances.

As they had done during the first term, the Clevelands moved out of the White House, making it their home only during the social season, and rented a nearby property, "Woodley." The primary concern for privacy, however, was less focused on the First Lady and more on their first child Ruth, born between the two Cleveland presidential terms, and their daughters Esther, the only presidential child born in the White House, and Marion, born at their summer home.

There was reason for genuine alarm when public interest in the children led some tourists on the South Lawn to one day rush the nurse of the presidential daughters pushing their carriage and giddily overwhelmed her, taking the babies out and handing them around. Despite the efforts of the First Lady, the public and press had an insatiable interest in the children and, as they had done to their mother, some elements of the manufacturing industry exploited the children by appropriating them in advertisements.

Frances Cleveland continued to perform her public role of hostess with a balance of warmth towards citizens of all races and classes and a regal social demeanor. During the second term, she became the first presidential wife to pay a call on a head of state, the queen regent of Spain who was then visiting Washington. She also voiced her personal support to the Princes Kaiulani of Hawaii in her efforts to convince Washington lawmakers to permit her to succeed to the Hawaiian throne which her aunt Queen Liliuokalani had been coerced from by American business interests; whether Frances Cleveland's sympathy for the effort to restore the monarchy influenced the President's sending of a new U.S. minister to Hawaii to facilitate the restoration (which failed) is, however, is unknown.

Post-Presidential Life:

Frances Cleveland had two periods as aformerFirst Lady, each following the non-consecutive terms of her husband; the first ran from March 4, 1889 to March 3, 1893. The second period followed McKinley's March 4, 1897 Inauguration.

During the first period, the Clevelands lived on Madison Avenue in New York City and led a relatively quiet life; during this period Frances Cleveland gave birth to her first child Ruth, and the baby became celebrated in the popular culture of the time.

Following her permanent departure from the White House in 1897, she joined the former President and their children in creating a new life in Princeton, New Jersey for what was the second period of her life s a former First Lady.

She focused her time on her children, turning down the presidency of the Daughters of the American Revolution, for example, because of the political obligations she knew would be associated with the position. Her two sons were born within six years and four months after leaving the White House, thus making her the only First Lady to give birth to children after her incumbency there had expired.

A year after her last child was born, however, 12-year old Ruth died of diphtheria in 1904 and Frances Cleveland sank into a severe depression. Four years later Grover Cleveland died, leaving her a 44 year old widow with four children. She took them all to Europe for an extended stay, from September 1909 to May 1910.

Frances Cleveland had continued to serve as a Wells College trustee as she had since 1887 and in was in that capacity that she pushed for the school's art history professor Thomas Jex Preston, Jr. (1863- 1955) to assume the presidency of the college upon the enforced resignation of its outgoing president; she had befriended Preston, a successful manufacturer, classicist, archaeologist and Ph.D. art student.

Frances Cleveland had also endowed a chair at the college to which Preston was appointed. He also became her second husband when they married on 10 February, 1913. She and her husband were feted before their wedding with a White House dinner hosted by First Lady Nellie Taft. In April of 1914 the former First Lady and her new husband moved to London to live for nearly a year.

When war broke out in Europe later that year, the new couple returned to the U.S. and in 1915 involved themselves in the patriotic, non-partisan National Security League. The group propagated democracy and a strong national defense in preparation for world war through military regiment-type "Squadrons." Frances Cleveland Preston began speaking to large auditoriums of citizens, exhorting them to taking the threat of war seriously. In November 1918, she assumed the NSL positions of Director of the Speaker's Bureau and The Committee on Patriotism through Education.

Although the former First Lady had avoided controversy throughout her public life, her work with the NSL proved otherwise. She suggested that Americans did not unite in support of a strong defense because of what she called the "huge percentage of unassimilated population that cannot think or act together." The sense of psychological indoctrination and use of fear in classrooms to inculcate children seemed to cross a line within the ranks of the organization and Frances Cleveland Preston resigned from the organization on December 8, 1919. Equally controversial was her contention that women were yet intelligent enough to vote and when they were given the vote, were not successful in politics and should instead focus their civic activities on welfare charities. In May of 1913 she was elected as vice president of the New Jersey Association Opposed to Woman's Suffrage and served as the president for the Princeton chapter.

Although she generally avoided the press, Frances Cleveland Preston led an active public life. She was captured at least one known time on film, appearing as part of an entourage with former President Theodore Roosevelt during a World War I Liberty Bond rally held in Baltimore where the other notable in attendance was that city’s Catholic Archbishop Gibbons. Here is a video clip of that footage:

FRANCES CLEVELAND VIDEO FOOTAGE; YOUTUBE URL:

http://www.youtube.com/watch?v=M-a_W5AjWFY

During World War I and the Great Depression, her needlework skills were joined with thousands of other similarly-talented women who made thousands of necessary clothing, linens and bedding as part of the Needlework Guild. She served as the treasurer of the organization's Guild's Princeton division from 1921 to 1924, then as its national president from 1925 to 1940. In 1928, she delivered a formal speech that was heard on the radio at the group's national convention.

Frances Cleveland Preston served on the Campfire Girls Board of Directors, appointed in 1925 while also served as that organization's president until 1939. When she was mistakenly misdiagnosed with the impending blindness, she immediately learned Braille and to translate materials on a Braille typewriter; despite her relief at learning her sight would remain intact, she continued to type reading materials up, specifically for a blind Navajo Indian teacher who could ill-afford to purchase the specially-prepared texts.

She remained active in the university life of Princeton and made her last public appearance at its June 1946 bicentennial celebration, joining former White House residents Edith Wilson and Herbert Hoover, as well as the President and Mrs. Truman and General Dwight Eisenhower.

Death:

Baltimore, Maryland

29 October, 1947

Burial:

Princeton, New Jersey

*Frances Cleveland lived for a longer period of time after leaving the White House (51 years) than any other First Lady.

ROSE ELIZABETH CLEVELAND 

.

 First Lady of the Cleveland Administration

4 March 1885 - 2 June 1886 (beginning of first term)

Grover Cleveland was the second man who entered the presidency as a bachelor, but the only one who began his term as a single man and ended it as a married man (Buchanan, the only other bachelor elected to the presidency remained unmarried throughout his Administration). For the first fourteen months of the Administration, his youngest sibling sister Rose Elizabeth Cleveland served as the official hostess. Although she was developing her own independent career as a writer, editor and lecturer, she had begun to assume management of his domestic life as Governor of New York towards the end of his term. She presided over the party of friends and family who gathered in the governor’s mansion in Albany, New York to celebrate his victory in the 1885 presidential election.

Rose Elizabeth Cleveland, always called "Libbie" by her friends and family, was born 13 June, 1846; she was educated at the Houghton Seminary and taught literature in Lafayette, Indiana and later at Hamilton College.

Publicly, Rose Cleveland was considered a "bluestocking," a serious, academic woman with little patience or interest in those subjects which women of her era were socialized to find most compelling, such as clothing, decorating and entertaining. This is only a partial truth; as she revealed in one of her books, Rose Cleveland believed strongly in adhering to the societal conventions which dictated behavior and gender interaction. Her private letters, however, do reveal the frustration she experienced as a result of her nevertheless feeling she must adhere to the unwritten code dictating the protocols followed by Victorian-era First Ladies which limited her from dining in private homes or appearing in the public markets. That code did, however, permit First Ladies to appear in public theaters and like Mary Lincoln and Julia Grant, Rose Cleveland greatly indulged this personal passion. She had a particular love for the contemporary musical theater productions of Gilbert & Sullivan and managed to even coax her hard-working brother out of the White House to attend the theater with her.

Rose Cleveland’s facility with the classics prove useful to her during the long hours she was required to stand while shaking hands with endless lines of guests at White House receptions. Finding this especially dull, she later revealed that she was conjugating Greek and Latin verbs in her mind during this process. While she largely remained disinterested in politics, she didn't hesitate to express her anti-Catholicism to the President in her warnings to him not to appoint too many "papists" to federal positions.

Most of her friends were theatrical or literary professionals. Rose Cleveland was herself notable as the first First Lady, though not a presidential wife, to publish books she wrote during her incumbency. Her first bookGeorge Eliot's Poetry and Other Studieswas published while she was in the White House, in June of 1885; it went through 12 editions in a year and earned her some $25,000. While still serving as First Lady, the following year she publishedYou and I: Moral, Intellectual and Social Culture, a 545 page treatise considering the changes wrought on 1886 American life. Her last book,The Soliloquies of St. Augustine, translated into English,With Notes and Introduction by the Translatorwas published in 1910 by Little, Brown, and Company.

Rose Cleveland’s last efforts as First Lady were to enact the arrangements dictated by her brother for his White House wedding to Frances Folsom.

Following the assumption of the First Lady role by the new Mrs. Cleveland, Rose Cleveland moved to Chicago, where she worked as an editor of the city’sLiterary Lifemagazine for three years. The income she received from her book royalties soon accumulated and proved considerable. Able to support herself well by lecturing and writing, Rose Cleveland left her job in Chicago. She then returned to the city of Utica, New York, where she purchased her own home. Beginning in 1889, however, she had also begun heading south to Naples, Florida. There she bought two property lots for twenty dollars and had her own cottage built there on Gulf Street, five blocks from the pier.

While there, the 44 year old Rose Cleveland began a romantic friendship with Evangeline Simpson, a wealthy 30-year-old widow. It soon developed into a physical love relationship. In one of her first letters to the woman she called “Eve,” the former First Lady declared, "Ah, how I love you…you are mine by every sign in Earth and Heaven--by every sign in soul and spirit and body…Oh, Eve, I tremble at the thought of you. Sweet, Sweet, I dare not think of your arms." Later in 1890, Rose Cleveland proposed that they meet in New York but rather than stay with the former President and First Lady at their Madison Avenue home, she wanted to share the same hotel room with Eve Simpson, an arrangement the latter agreed to.

The two women decided to live together, an arrangement which continued until Eve Simpson chose to follow a more conventional path. In 1895, she became engaged to Henry Benjamin Whipple, the widower Episcopal bishop of Minnesota. She was 36 years old and he was 74 years old. The decision, Rose Cleveland wrote, hurt her deeply. Nevertheless, in a letter she wrote to Bishop Whipple on Executive Mansion stationery while visiting her brother during his second term, she expressed her genuine wishes that the couple had found love with each other.

He died in 1901, and after Evangeline had observed the traditional one-year of mourning, she abruptly left for Europe and was joined by Rose, the two women living together in Italy. The two women settled there permanently in 1910. Evangeline Whipple lived for 12 years beyond Rose Cleveland, who died on 26 November, 1918. The two women are buried alongside each other in Italy.

Bishop Whipple died in 1901 and within four years Rose Cleveland and Eve Simpson Whipple had resumed their contact by letter. They decided to both leave the United States and live together in Italy. When they sailed on a Cunard Line ship to Europe in 1910, the two women unapologetically booked a cabin together.

They settled in Bagni di Lucca, in Tuscany, living a life unbothered by publicity, until Rose Cleveland died of the Spanish flu epidemic on 22 November 1918 epidemic. 

Despite her status as a former First Lady, her remains were not returned to the United States, but rather she was buried in the American Anglican Church Cemetery in the town where she had lived with Eve Simpson Whipple and another woman friend who had come to share their household. Upon her death in 1930, Eve Simpson Whipple was buried next to Rose Cleveland as stipulated in her will.