A definitive answer remains elusive, but here are the 13 chief executives for whom I've found evidence of some presence in Brookline before, during, or after their presidency.
Washington was in command of the Continental forces besieging Boston from July 1775 until the British evacuation on March 17, 1776. The main route between Washington's headquarters in Cambridge and key fortifications on Dorchester Heights and elsewhere passed through Brookline.
Various secondary sources report the general traversing this route at various times, and it seems likely that he did on several occasions. There are also unconfirmed stories of his having inspected the Brookline Fort at Sewall's Point during the siege.
Washington certainly passed through Brookline during a visit to Boston in October 1789, six months after his inauguration as president. William Sumner, who was a boy of 9 at the time, described the visit 71 years later in the New England Genealogical Register. After inspecting the militia on Cambridge Common, reported Sumner, the president ("on a noble white charger") and a large procession set out for Boston.
Leaving Cambridge, the procession crossed Charles river over the old Cambridge bridge into Brookline. Thence passing by the Punchbowl tavern through Roxbury, they met at the dividing line between Boston and that town the officers and leading citizens of Boston, who came out to tender Washington the hospitalities of the metropolis.
JOHN ADAMS
John Adams' mother Susanna Boylston Adams, the daughter of Peter Boylston, was born and raised in Brookline. Adams made numerous visits to Brookline in the course of his long life.
The Rev. John Pierce was ordained as minister of Brookline's First Parish in March 1797, the same month Adams was inaugurated as president. Many years later, in 1849, Pierce shared this account of one of Adams' visits:
President Adams often mentioned with a lively interest this place of his mother's nativity. While President of the United States, he called on the Hon. Jonathan Mason, where General Theodore Lyman's house now stands, and remarked, as a striking illustration of the changes in the manners and customs of the country, that the last time he had travelled over the road before, he carried his mother, horse-back, on a pillion behind him.1
Perhaps the last visit of Adams to Brookline was described by John William Denehy in his 1906 history of the town:
In 1821, President Adams, then 86 years of age, having expressed a desire to again visit the house in which his mother was born, a grand dinner party, given in his honor by Mr. David Hyslop at which Governor Brooks, General Sumner, and other distinguished guests were present, was held at the old Boylston House, which had been purchased from the heirs of Dr. Za[b]diel Boylston, by Mr. Hyslop's father.2
JOHN QUINCY ADAMS
Evidence of John Quincy Adams in Brookline, birthplace of his grandmother Susanna, is sparse, but Paul C. Nagel in his biography of Adams (John Quincy Adams: A Public Life, A Private Life, Harvard University Press, 1999) mentions Brookline as one of several towns where the former president made lyceum speeches in 1842.
Adams was certainly aware of his Brookline heritage. In his memoirs, he mentions speaking with the Rev. John Pierce of the First Parish Church at a dinner in Washington in September 1826, less than two months after his father's death:
Mr. Pierce spoke to me of the remains of my father's maternal family at Brookline—Boylstons and Whites—and of the ancient family estate in that town, which has gone into other hands.3
ULYSSES S. GRANT
Like J.Q. Adams, Ulysses S. Grant's presence in Brookline is only alluded to (at least in in the evidence I've seen so far). In an 1896 history of the town, Charles Knowles Bolton, writing about Brookline resident and railroad president Ginery Twitchell during the Civil War, noted that
Years afterward, Mr. Twitchell entertained in Brookline the great military leader of the war, General U.S. Grant. The general walked into the fields east of Kent street to see some wild animals kept by Mr. Twitchell's son.4
Another Ulysses S. Grant—the president's grandson Ulysses S. Grant III—lived on Brington Road in Brookline for a short time in the early 1900s while on military duty in Boston. Grant and his wife Edith, the daughter of Teddy Roosevelt's Secretary of State Elihu Root, moved to Brookline after a Washington wedding attended by President Roosevelt and many U.S. and foreign dignitaries.
BENJAMIN HARRISON
Benjamin Harrison, elected in 1888 between the two terms of Grover Cleveland, took an excursion to Brookline by carriage in August 1889 during a visit to Boston, part of a week long New England sojourn.
Late in the afternoon of August 7th, the President and a large party, riding in carriages and accompanied by mounted officers, set out on a ride through Brighton and Brookline. They climbed to the top of Corey Hill and proceeded from there to a reception at the home of Congressman John Candler on High Street Hill before returning to Boston.
See my earlier post Presidents in Brookline: Benjamin Harrison for more on Harrison's Brookline visit.
THEODORE ROOSEVELT
While a student at Harvard, beginning in 1876, Theodore Roosevelt had an active social life. "The young collegian," wrote William Draper Lewis in a 1919 biography, "became a familiar figure in Cambridge and Boston—especially in Brookline—driving about in a sort of sporting phaeton, then the height of the New York style in equipages."5
But it was in Chestnut Hill in Newton in 1878 that Roosevelt was introduced to his future wife, Alice Hathaway Lee. She was the cousin and next-door neighbor of Roosevelt's Harvard classmate Richard Saltonstall. At 17, she was two years younger than Roosevelt.
After what was described as a tumultuous courtship, they were married on October 27, 1880—Roosevelt's 22nd birthday—in the First Parish Church in Brookline. Alice Roosevelt died a little over three years later, on February 14, 1884 from Bright's Disease and complications from childbirth. Roosevelt was devastated and was said to rarely speak about Alice thereafter.
WILLIAM HOWARD TAFT
William Howard Taft, who succeeded Theodore Roosevelt as president, spent the summers from 1909 to 1912 in his "summer capital" along the shore in Beverly, Massachusetts. In September of the first year of his presidency, Taft came to Brookline for a field day held in his honor by the Yale Club of Boston.
The president (Yale, Class of 1878) played a round of golf at The Country Club, followed by a luncheon in his honor at the nearby home of Herman L. Whipple. As the New York Times described it:
The President motored from the club grounds to Mr. Whipple's home, where the latter had invited a company of nearly 300 Yale men to meet President Taft at luncheon. Following the luncheon came a reception under one of the towering elms on the Whipple lawn. After the entire company had passed by in a single column and had shaken hands with the President, some one stopped and asked for an autograph on his menu card. The idea was no sooner suggested than a hundred or more of the college men were swarming about the President in quest of similar souvenirs.6
Taft later watched the first inning of a baseball game between former Yale players before leaving for the return trip to Beverly. (Asked to umpire the game, Taft declined, saying, according to the paper "I value my life too much for such a job as that.")
Four years later, Taft was at The Country Club again, in the gallery for the first day of play at the 1913 U.S. Open, the year Brookline's Francis Ouimet won his historic victory over British stars Harry Vardon and Ted Ray. In October 1915, the then ex-president Taft spoke in favor of the proposed League of Nations before 1,300 people in the Harvard Congregational Church on Harvard Street.
FRANKLIN DELANO ROOSEVELT
Franklin Roosevelt, like his cousin and presidential predecessor Theodore, took part in a wedding in a Brookline church. In FDR's case, it was not his own wedding but that of his oldest son James.
James Roosevelt and Betsey Cushing were married at St. Paul's Episcopal Church on June 4, 1930. Franklin Roosevelt was governor of New York at the time. The bride's father was renowned neurosurgeon Harvey Cushing of Brookline.
More than 500 guests—"leaders of the medical, political, diplomatic and social worlds," according to the New York Times—were in attendance. Spectators, noted the Boston Globe, thronged the neighborhood around the church.
Several thousand intensely curious persons followed the incidents of yesterday's marriage and the reception following, with avid interest [reported the Globe]. The crowd of onlookers around the church grounds, in the triangle at Aspinwall av and St Paul st, was so great that it took a large force of policemen and motorcycle men to keep the surrounding streets free of congestion so that the machines conveying members of the bridal party and the guests might reach the church door conveniently.
The church lawns were overrun with people on the Aspinwall av and St Paul sides. Verandas and steps of neighboring houses were used as points of vantage from which to watch the arrival of guests and later that of the bridal attendants and the bride herself.7
The ceremony was followed by a reception on the grounds of the Cushing home on Walnut Street where about a dozen large tents were erected on all sides of the mansion, including one with a dancing floor over the tennis courts.
James and Betsey Roosevelt were divorced in 1940.
JOHN F. KENNEDY
John F. Kennedy, of course, is the only U.S. President born in Brookline. Kennedy was born May 29, 1917 in the family home on Beals Street, now a National Historic Site administered by the National Park Service and open to the public.
Kennedy lived in the Beals Street home for six years before moving with his family to a larger home on Naples Road nearby. Kennedy attended both the Edward Devotion School and the Dexter School in Brookline before the family moved to New York in 1927. He was baptized and served as an altar boy at St. Aidan's Church on Pleasant Street.
GEORGE H.W. BUSH & GEORGE W. BUSH
George H.W. Bush was a former president and George W. Bush was seeking the Republican presidential nomination when they attended the Ryder Cup golf tournament together at The Country Club in Brookline in 1999.
The younger Bush's attendance at the match between U.S. and European golfers was not without controversy. Bush, then governor of Texas and leading in Republican polls, skipped the California Republican Convention to attend the tournament. That drew criticism from some of his rivals for the party's nod, but did nothing to derail Bush's drive toward the eventual nomination and the White House.
BILL CLINTON
Bill Clinton made two appearances at campaign events in Brookline during his successful 1992 quest for the Democratic nomination for president. Clinton met with members of the Brookline Democratic Committee in January. In April, he was back for a fund raiser at the home of Robert Farmer, his national campaign treasurer.
Clinton's January visit with the Brookline Democrats was paired with an appearance before the South Shore Chamber of Commerce in Dedham, a pairing the Boston Globe saw as indicative of his ability to reach out to different segments of the party.
Presidential hopeful Bill Clinton straddled the yin and yang of Massachusetts Democratic politics last week, [said the Globe] pitching his middle-class pragmatism in separate events to Dukakis Democrats in Brookline and Silber Democrats in Dedham, and leaving both crowds smiling.8
BARACK OBAMA
It was suggested when I first wrote this piece that Barack Obama may well have been in Brookline while a student at Harvard Law School, perhaps to eat in one of Brookline's restaurants, shop at its stores, or catch a movie at the Coolidge Corner Theatre. Evidence of such an early visit may yet turn up. But Obama definitely came to Brookline on May 18, 2011, making one of his two fundraising stops that day at the home of Jack & Eileen Connors in South Brookline.
NOTES
1 "An address at the opening of the Town Hall, in Brookline: on Tuesday, 14 October, 1845." (A pillion is "a pad or cushion put on behind a man's saddle chiefly for a woman to ride on." - Merriam Webster Online.
2 A history of Brookline, Massachusetts, from the first settlement of Muddy river until the present time: 1630-1906
3 Memoirs of John Quincy Adams, comprising portions of his diary from 1795 to 1848, Volume 7
4 Brookline: the history of a favored town
5 The life of Theodore Roosevelt
6 "President has fun with old Yale Men." New York Times, September 8, 1909, p. 10.
7 "Miss Betsey Cushing married as throng surrounds church." Boston Globe, June 5, 1930, p. 12
8 "Clinton finds favor playing to 2 audiences." Boston Globe, January 21, 1992, p. 12
Presidential images from whitehouse.gov












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