From the Historian

From the Historian: A Complex Man of Conscience, Trinity Parishioner Robert C. Winthrop

Cynthia Staples
December 3, 2025

Dear Trinity Church and friends,

Walk down the center aisle of Trinity Church. Midway toward the altar, stop and look to your left. You will see a stained-glass window depicting two angels holding scrolls. An 1888 historical account of the church describes the window as, “typical of Hope, the motto of the Winthrop arms.” Robert C. Winthrop commissioned the window in memory of his parents. At the bottom of the window in Latin are the words, “A surviving son to the best of parents.”

This surviving son, born in 1809, the youngest of thirteen children, became an eminent politician and orator at the state and national level. A newspaper once noted that Winthrop was “said to have, by his eminent ability, impartiality, and gentlemanly bearing, won the respect and esteem, even of his political opponents. … there was no man in the Whig ranks so acceptable to his party for the office of Speaker of the House…”

Winthrop’s own son wrote “in looking back over his exceptionally long life [my father] felt that he had received, on the whole, ample recognition of any services he might have rendered to the causes of religion and philanthropy, or in the fields of history and oratory. As a statesman, however, he considered that he had not always been fully understood or fairly represented …” Winthrop felt most misunderstood regarding slavery.

In 1820, when Winthrop was eleven years old, the U.S. legislature passed the Missouri Compromise admitting Maine as a free state and Missouri as a slave state. That act prohibited slavery in the remaining territories of the Louisiana Purchase north of the 36 30 parallel. But then over thirty years later, the Kansas-Nebraska Act of 1854 allowed residents of these territories to decide on the issue of slavery through popular sovereignty, thus repealing the Missouri Compromise. Fiery debate and violence followed earning Kansas the nickname “Bleeding Kansas” as pro-slavery and anti-slavery factions clashed.

Winthrop served in Massachusetts House of Representatives from 1834-1840. He entered national politics and was elected to Congress in 1840 and served as Speaker of the House of Representatives from 1847-1849. He served during a tumultuous period in U.S. history. The nation sought to expand its borders while grappling with slavery in the southern states and its potential expansion across a growing country.

While Winthrop was decidedly anti-slavery, he and his party struggled with how to affect nationwide abolition. He had seen abolition take many forms. Great Britain abolished slavery across the British Empire in 1833 with the passage of the Slavery Abolition Act. A key component of that plan’s success was the compensation of slaveholders for the loss of their property. It took until 2015 for British taxpayers to finish paying off the incurred debt. Those compensated included individuals and institutions around the world who owned estates in the colonies, sometimes as absentee landowners and as mortgage holders.

While Massachusetts abolished slavery in 1783, that did not necessarily impact peoples’ interests outside of the state. Trinity Church vestryman John Hubbard owned an estate, Mainstay, in British Guiana, now known as Guyana. Records note Britain awarded his estate 1,775 pounds for the freedom of 338 enslaved people. Hubbard’s brother-in-law Gardiner Greene had already sold his plantation, Evergreen. Mary Judith Benjamin Lanman, married at Trinity in 1826, made claims for two estates. She received compensation for five enslaved people in Guyana but was unsuccessful in her claim for 73 enslaved people in Barbados.

Winthrop may have watched with dread as abolition of slavery in the U.S. took a vastly different path. Thirty years after Britain’s Abolition Act, Civil War tore the U.S. asunder. It was the Union (Northern states) versus the Confederacy (Southern states). For some it was a fight to end slavery, and for others it was a fight asserting, or reigning in, states’ rights.

During the war, effective January 1, 1863, President Abraham Lincoln issued an Executive Order declaring that over 3.5 million enslaved people in the South were free; the Emancipation Proclamaton. In 1865, he was assassinated, and Vice President Andrew Johnson assumed the Presidency. A southern sympathizer, he immediately worked to reestablish white southern privileges and strip away newfound opportunities for Blacks.

As he watched these events unfold, Winthrop mused, “For myself, I do not see what Johnson could do except what he is doing and has done. The idea of holding the South in subjection for an indefinite period, until negro suffrage can be forced upon them, is abhorrent to me. Punish the immediate authors and abettors of the rebellion if you will, but it will not be wise to make too many martyrs for the South to canonize. …”

Winthrop’s cautious language overshadowed his actions. In 1872, in a letter to a friend, after reading a book about “the Rebellion,” he makes note in his critique that the author makes no mention of his actions against slavery.

“[Giddings’s] allusions to myself are quite temperate. His omissions in regard to my course are more extraordinary than his expressions. … He makes but slight reference to my Resolutions & none at all to my Report, on the Imprisonment of Colored Seamen … “

Winthrop refers to a practice begun in 1822 in Charleston, South Carolina. Once a ship docked at port, a harbor master boarded. Black sailors were seized and escorted from the ship. Whether free or enslaved with papers, the Black sailors were taken to jail, imprisoned until their ship was ready to depart. The cost of the incarceration was charged to the sailors or their employers. It was state law.

A Negro Seaman’s Act first passed in the state of South Carolina after the failed enslaved insurrection led by Denmark Vesey. Other states soon followed including Alabama, Florida, Georgia, Louisiana, North Carolina, and Texas. The practice would not end until the Civil War. Until then, each year hundreds of Black sailors, including those from England, were detained at southern ports, imprisoned, and threatened with sale at public auctions. They were imprisoned out of fear that they would inspire and incite further enslaved insurrections.

In Congress, Winthrop was besieged by Massachusetts merchants who depended on the smooth flow of maritime commerce, especially southern cotton for New England textile mills. They wanted their sailors, and any other free person of color, protected. In 1843 Winthrop spoke passionately about the subject before Congress, but to little avail. The southern states claimed it was their right to enact such laws.

In 1845, Winthrop spoke against the annexation of Texas as a slaveholding state. He also made several speeches against the war with Mexico as unjust simply for the acquisition of more territory.

On September 18, 1850, Congress passed the Fugitive Slave Act as part of the Compromise of 1850. The act required that slaves be returned to their enslavers, even if they were in a free state. The act also made the federal government responsible for finding, returning, and trying enslaved persons. While acknowledging the constitutional rights of the South to certain provisions for the return of fugitives, Winthrop refused to consent to any law which did not provide for a fair trial by jury and the writ of habeas corpus.

He said, “I hold it to be a just and reasonable provision, and one which ought to form a part of any bill which shall be passed for this purpose. There is a preliminary question, and that is whether he is a fugitive at all, whether he belongs or owes service to anybody. It must always be a question whether such a person be your slave or whether he be our freeman question which should be tried where he is seized and when the immediate liberty which he enjoys is about to be taken away from him. I am in favor of recognizing the right of trial by jury in all cases where a question of personal liberty is concerned.”

As Winthrop’s political career faded, he intensified his commitments to civic efforts. He presented the new Boston Public Library with one of its early large gifts of books. For a time, he was president of the Massachusetts Bible Society and Children’s Hospital in Boston. He was a respected eulogist, historian, and orator. He presided over the Massachusetts Historical Society for thirty years and was a member for over fifty. He served as Chairman of Boston’s Board of Overseers of the Poor. He also led the Board of the Providence Society, an association of Boston charities.

In 1874, Charles Sumner died. Sumner was a U.S. Senator from Massachusetts who was leading advocate for abolition. One of the many people praising Sumner’s legacy was Trinity’s Rector Phillips Brooks. Brooks spoke about Sumner on a Sunday morning at the end of his sermon.

In his diary, Winthrop wrote in response to his Rector’s praise. “… He spoke of [Sumner] as one who was ‘a friend to freedom when others were its enemies,’ and as ‘hating slavery when others loved it.’ … We [the Whig party] did what we could to keep the peace between North and South, hoping that a day would one day be opened, in the good providence of God, for gradual emancipation on some basis which would be safe for both blacks and whites. … we had always looked to the ultimate disappearance of slavery under the influence of civilization and Christianity, without endangering the Union or sacrificing half a million lives. …”

In his 1882 autobiography, Frederick Douglass wrote scathingly of Winthrop: “During the war he was too good to be a rebel sympathizer, and not quite good enough to become … a power in the Union cause.” In later years Douglass, upon reflection, would retract his statements and applaud Winthrop for what he had done.

Winthrop was particularly interested in education. He believed that education was vital to all people regardless of race or class. “The influence of education, or of the want of education, on the welfare of our land can have no territorial limits or boundary lines. … Colleges in South Carolina or Tennessee or Virginia are United States colleges and are as important to the welfare of the country as Yale or Harvard or Columbia. Illiteracy and ignorance are no mere local dangers, whether among whites or blacks. They are dangers to law and order and true liberty everywhere…”

Winthrop spoke these words at the 1892 annual meeting of the Peabody Trustees. For twenty-five years he served as President of the Peabody Education Fund, a philanthropic enterprise established by his friend George Peabody after the Civil War to support education initiatives at existing schools in the southern states.

A devout Episcopalian, Winthrop served as a vestry member at Trinity Church for sixty years. In the spring of 1877, documents show that he rented pew 94 where he could have easily turned to see the window he had commissioned in memory of his parents. Two angels holding scrolls. The scroll in the hands of the angel on the left reads, “And now Lord what is my hope.” The scroll on the right reads, “Truly my hope is even in thee.”

Robert Charles Winthrop died in 1894. Obituaries described him as “Boston’s grand old man.” His funeral took place at Trinity Church. Rector E. Winchester Donald officiated with Bishop Lawrence in attendance. At his family’s request, the service was kept remarkably simple. He is buried at Mount Auburn Cemetery in the Winthrop Family Mausoleum.

Until next month,

Cynthia

Images

Robert C. Winthrop https://www.metmuseum.org/art/collection/search/268316

Reynold’s Political Map of the United States 1856 https://www.loc.gov/item/2003627003/

Proclamation of Emancipation 1865 https://www.loc.gov/item/2020780958/

African American Sailor, ca. 1861 https://www.loc.gov/resource/ppmsca.11280/

Sources and Further Reading

Bardes, John. Sailing While Black. The Story of Free Black Sailors Trapped in Louisiana’s Slave Prisons. 64 Parishes. Updated March 22, 2023. https://64parishes.org/sailing-while-black

Borome, Joseph. “Two Letters of Robert Charles Winthrop.” The Mississippi Valley Historical Review, vol. 38, no. 2, 1951, pp. 289–96. JSTOR, https://doi.org/10.2307/1895595.

Douglass, Frederick. The Life and Times of Frederick Douglass. Park Publishing Co. Hartford, CT 1882. https://archive.org/details/lifetimesoffrede1882doug

Goodwin, Daniel. In Memory of Robert C. Winthrop. Chicago. Privately Printed. 1894. https://archive.org/details/inmemoryofrobertgood

The Hon. Robert C. Winthrop. Daily Evening Transcript. February 28, 1848. Vol. XIX, Issue 5397, p.2.

The Last Scene. Boston’s Grand Old Man is Laid at Rest Today. Boston Daily Journal. November 21, 1894. Vol. LXI, Issue 20156.

Winthrop, Robert C. A Memoir of Robert C. Winthrop. Prepared for the Massachusetts Historical Society. 1897. https://archive.org/details/memoirofrobertcw0000unse_v3w1/page/n5/mode/2up

Trinity Church Archives Baptism, Marriage, and Pew Records