Little is known of Maude's successor, John Woodbridge, except that he is supposed to have been the first minister at Andover and that he remained in office for approximately one year. In 1650, Robert Woodmansey became the schoolmaster with a salary of "fifty pounds a year." He was followed in 1667 by the famous colonial poet and physician Benjamin Thompson.

On December 29, 1670, the celebrated Ezekiel Cheever was invited to become Head Master. Cheever was well known throughout the colonies, for he had written the famous Accidence, which was the accepted Latin grammar. In 1704 the school moved to the present location of the statue of Benjamin Franklin on School Street. Upon his death on August 21, 1708, Cotton Mather, the renowned divine, remarked, "We generally concur in acknowledging that New England has never known a better teacher."

Nathaniel Williams, the first pupil to become Head Master, succeeded Cheever. When he resigned in 1734, his assistant, John Lovell, was appointed to the vacancy, becoming "the pride of Boston's parents and the terror of its youth."

In winter it was not unusual for the boys to bring their sleds to school with them and, as soon as school was over, to coast down Beacon Street, across Tremont, and down School Street. During the winter of 1774-75 General Haldimand (see Footnotes), a commander of British troops under General Gage, lived on School Street and had one of his servants ruin the coasting area by putting ashes on it. "The lads made a muster" — probably of the first cIass — "and chose a committee to wait upon the General, who admitted them, and heard their complaint, which was couched in very genteel terms, complaining that their fathers before 'em had improved it as a coast from time immemorial." He ordered his servant to repair the damage, saying that he had trouble enough with Boston men, and wouldn't have any with Boston boys. He "acquainted the Governor with the affair, who observed that it was impossible to beat the notion of Liberty out of the people, as it was rooted in 'em FROM THEIR CHILDHOOD." (see Footnotes)

The school adopted a four-year course of study in 1789.

Per the Catalogue of the Public Latin School, in 1793 it was determined that “the stated time of admission to the Latin School be July annually, but admission may be obtained at other times, and in such classes as the candidate upon examination shall be found qualified.”

School was resumed under Samuel Hunt, who ruled with some difficulty until 1805. He was succeeded by William Bigelow, who resigned after nine trying years. In 1812, a new building of three stories was constructed on the site of its previous location.

Benjamin Apthorp Gould, appointed Head Master in 1814 while still a senior at Harvard, restored order and scholarship. Many features of the Latin School of today — among them the "misdemeanor mark" and the practice of declamation — were initiated under Gould. America’s first public school extended to a 5-year course of study in 1814. Until 1814 boys usually entered at the age of seven years. In 1814 a regulation was made by which none younger than nine years old were admitted. Gould also fostered the beginnings of a library and issued regular reports of scholarship to parents, placing squarely on them the responsibility for the pupils' conduct.

In the early 1800s, elements of the admission process remained in place to demonstrate adequate preparedness for the Public Latin School's demanding course of study, including an entrance examination to show proficiency. During this time, educational opportunities for Boston's youth expanded from Latin's curriculum, rooted in the Classics, with the creation of another examination school in 1821 offering a curriculum intended for its graduates to achieve success in the world of commerce and industry, English High School — the nation’s first public high school.

School Street was the home of the Public Latin School, in various locations, for approximately 200 years.

Latin School owes much to Epes Sargent Dixwell, who succeeded Dillaway, for during his 15 years as Head Master, he founded the Boston Latin School Association in 1844 and made Gould's dream of a school library a reality. 1844 also marked the establishment of a new school building on Bedford Street. By 1847, the required age for applicants was changed to twelve years old.

When Dixwell resigned in 1851, Francis Gardner, one of the most celebrated men of mid-nineteenth century Boston, was appointed his successor. Gardner edited the famous series of Latin School textbooks. A rugged, forthright character, he made both friends and enemies.

The landscape of public education was expanding again in Boston as Girls' High School was established in 1852 as the first public high school for girls in the country, with a focus on training as teachers.

In 1855, the Massachusetts legislature passed the country’s first law prohibiting school segregation on the basis of race, supported by arguments made in Roberts v. Boston (1850), by one of the country’s first African American attorneys, Robert Morris, and Charles Sumner, Class of 1826, a leading abolitionist lawyer.

In 1870, the course of study increased to eight years.

During the last six years of Dixwell’s tenure, he unsuccessfully opposed the imposition on the school of a "general culture" curriculum. He died in 1876, the first Head Master to die in office since Ezekiel Cheever.

The first African American graduate of the Public Latin School was Parker Bailey, Class of 1877.

Another example of barriers to education being reconciled in the mid- to late-19th century was the establishment of Girls' Latin School, founded in 1877, as the first public, college preparatory high school for young women in the U.S. These early, groundbreaking schools for girls — which soon developed a challenge, not unfamiliar to the Public Latin School, of not enough seats and resources to meet demand — conducted admissions through an entrance examination to determine preparedness.

Again, in 1880, the length of study at Latin School was adjusted. The years of enrollment were reduced from 8 to 6 years. The school was relocated to Warren Avenue in 1881.

In 1886, a regulation was made requiring that none younger than ten years old were admitted. 1887 marked the year of the establishment of the Thanksgiving Day High School Football Game rivalry between Boston Latin School and English High School on Boston Common. In the early years of the rivalry, the teams often wore variations of collegiate uniforms: Latin wore Harvard Red and English wore Yale Blue.

Augustine Milton Gay was chosen as Dixwell’s successor, but he lived only a few months after his appointment. Dr. Moses Merrill was appointed next and continued in office until 1901. His contribution to the school was the reorganization of the curriculum on a more modern basis.

Early in the 20th century, while still serving its original mission for its graduates to achieve success in industry/trades, the English High School changed its admissions policy to no longer require an examination, around the time of its centennial.

Arthur Irving Fiske became Head Master in 1902. One of the ablest scholars in Massachusetts, he was loved and respected by his pupils. He resigned in 1910 and was succeeded by Henry Pennypacker, who brought to the office of Head Master not only the mind of the scholar but also the rugged personality of the athlete. He resigned in 1920 to become chairman of the Committee on Admissions at Harvard. His work there made him a figure of national importance.

In 1920 Patrick Thomas Campbell, '89, became the first graduate of Latin School to sit in the Head Master's chair since Dr. Gardner. Enrollment doubled during his tenure. Even with this rapid growth, the school for four years in succession, from 1925 to 1928, obtained the highest average in college entrance examinations. This secured for the school permanent possession of the trophy given by the Harvard chapter of the Phi Beta Kappa Society. A new school building was built on Avenue Louis Pasteur in the Fenway neighborhood of Boston in 1922, where the school resides currently. In 1929, Mr. Campbell left to become an assistant superintendent of schools and in 1931, was elected Superintendent of the Boston Public Schools, a position he held until his death in 1937.

Joseph Lawrence Powers, '96, a Master in the school for 23 years, was appointed Campbell's successor. A soft-spoken, courteous man, Dr. Powers exerted an incalculable influence for nearly 50 years. He sustained the school's excellence through years of depression and war. He was also an energetic champion of the economic welfare of the Masters. From his retirement in 1948 until his death in 1955, he was dedicated to the prosperity of both the school and its alumni.

George Leonard McKim, '18, succeeded Powers in 1948. A veteran of two world wars, Mr. McKim gave over 30 years of service to the Boston Public Schools. During his tenure of office, the school received a great deal of publicity. National magazines reported favorably on the methods and standards of the school. The performances of the students on the National Merit Scholarship Examinations proved that these commendations were justified.

John Joseph Doyle, '12, became Head Master of his alma mater in 1954. Under Mr. Doyle's capable leadership, many changes were made in the school's curriculum. Four distinct courses — language, science, mathematics, and history — were set up in the upper classes. More electives and accelerated courses were also offered. The Advanced Placement program was established, giving many students the chance to receive credit for college courses on the freshman level. Mr. Doyle retired in June, 1964, after having served in the Boston Public School system for over 40 years.

Throughout Latin School’s history, students were required to demonstrate preparedness as qualified applicants via satisfactory grade achievement and an examination. In 1963, the Boston School Committee formalized admission requirements for BPS selective schools’ candidates requiring evidence of proficiency via grades and an exemplary score on a standardized, District assessment.

Dr. Wilfred L. O'Leary ’25, a veteran of World War II, was appointed Mr. Doyle's successor in September, 1964. As Head Master, Dr.O'Leary devoted himself to preserving the high standards of the school. Dr. O'Leary was the recipient of several awards for his outstanding educational leadership. During his tenure, Boston Latin School welcomed women students for the first time in September, 1972.

Starting in the fall of 1975, Judge W. Arthur Garrity ordered the integration of all Boston schools. For the exam schools, Judge Garrity ordered a set-aside system that required those schools to reserve 35% of their seats for underrepresented minority students.

This effort to address educational inequity was also supported by the Boston Latin School Alumni Association and the Boston School Committee, who voted to continue the policy — even after the court approved plan ended in 1989.

Dr. O'Leary was honored by teachers, alumni and friends of the school when he retired in June, 1976. The first female students, who entered as Class IV-B, graduated from Latin School also in June 1976. Mr. David Miller, a teacher at the school for over 30 years, assumed the position of Acting Head Master in September of 1976.

Michael G. Contompasis, '57, was appointed Head Master in April, 1977. Continuing the tradition of excellence, Mr. Contompasis broadened the educational vistas of the school. As a result, national attention was focused once more on Boston Latin School. In the fall of 1981, Money magazine rated BLS as one of the 12 top public schools in the country. 

Dr. Joseph F. Desmond, '44, both teacher and department chairman at his alma mater for 34years, assumed the position of Acting Head Master during the 1986-1987 academic year, when Head Master Contompasis was on sabbatical for study at Harvard University. Upon returning to his position in September 1987, Mr. Contompasis oversaw both the renovation of the main building and the construction of a new physical education addition to the building. During his tenure, in 1992, 1994, and 1995, Redbook magazine rated BLS the best school in Massachusetts. Sumus Primi. In recognition of his outstanding leadership, Mr. Contompasis in 1988 became the 35th recipient of the BLS Association's prestigious "Graduate of the Year Award." He served as head of school until appointed Chief Operating Officer of the Boston Public Schools in August 1998, and subsequently becoming Superintendent of the district from 2005 to 2007.

Cornelia A. Kelley H’44 was appointed Head Master in August 1998, the first woman to serve in that post. Ms. Kelley oversaw the construction of an addition devoted to the arts, with state of the art music and visual arts facilities, as well as a thorough renovation of the existing facilities. In the old cafeteria was built the Harry V. Keefe Library-Media Center, the most advanced school library in the world. In addition, the entire school was upgraded to the latest technologies appropriate to education. These renovations were made possible through city/state funding and the BLSA. In a time of national, state and local focus on education and standards, with the imposition of broad-based testing and close scrutiny of results, Ms. Kelley was charged with keeping the School at the forefront in curriculum, standards, and achievement. She retired in June, 2007 and was succeeded by Lynne Mooney Teta '86.

Following Dr. Mooney Teta’s resignation in June 2016, after several months addressing issues around racial climate, Michael G. Contompasis ’57 was appointed as the head master ad interim of Boston Latin School. He took on this role invigorated to work with “the entire Latin School community  — faculty, parents, students and alumni — to ensure that the school continues its work building a safe, respectful learning environment in which every student has the opportunity to achieve at his or her highest potential.”

Ms. Skerritt began her tenure in the fall of that year and immediately signaled a priority on student voice and expression, coupled with a commitment to deepen an appreciation for the diversity of culture and identities represented in the dynamic BLS community. From transforming assemblies into interactive experiences to creating a social media page that showcased the many accomplishments of the student body, Ms. Skerritt ensured that members of the school community and external BLS community members appreciated the vibrancy of academic and extra-curricular life. The leadership team of assistant heads of school and program directors worked to increase the frequency of classroom observations to provide real-time feedback on instruction in service of high student engagement and consistency within and across departments. In addition, the team worked to increase communication between home and school and increase student achievement by instituting individual parent-teacher conferences specifically for families of students who were struggling to find their footing in particular courses.

In March 2020, Boston Public Schools closed all schools due to the pandemic, COVID-19, and it wasn’t until September of 2021 that the full student body returned in-person to Avenue Louis Pasteur. Under Ms. Skerritt’s leadership, teachers pivoted to remote teaching in all disciplines, including the visual and performing arts. Faculty and students collaborated to maintain and deepen a sense of community across physical distance, holding virtual meetings, panels, and discussions on issues of utmost importance to the nation, particularly after the murder of George Floyd. It was a time filled with challenges and anxiety, while also demonstrating the resolve of our community and passion from our young people to improve the state of the world they are poised to inherit. Throughout this time of virtual (and later hybrid) learning, Ms. Skerritt maintained the committees and structures key to moving the school forward, including School Site Council, Equity Roundtables, and professional development workshops for staff.

The pandemic alongside the country’s racial reckoning also catalyzed shifts in the admissions process to the three exam schools in BPS (Boston Latin Academy, Boston Latin School, and the John D. O’Bryant School for Mathematics and Science). These changes included a transition from the Independent Schools Entrance Exam (ISEE) to the MAP Growth assessment, as well as institution of a system that built in greater geographic and class diversity by having students compete within 8 socio-economic tiers as well as allocating additional points to young people residing in public housing and/or attending schools with a significant number of low-income students. For the two admissions cycles immediately following the COVID-19 pandemic, the entrance exam was not offered due to the health risks of assembling students to test in person. Through all of these shifts, report card grades of Bs or higher were required for all students to be considered for admission.

Upon the return to campus, Head of School Skerritt (the title of “headmaster” had been replaced by “head of school” across the district) facilitated a comprehensive whole-school process that culminated in a set of BLS Core Values. After five years of leading alma mater with grace and grit through a tumultuous period of racial reckoning and a worldwide pandemic, she announced her resignation, effective at the end of the 2021-22 school year.

After a robust screening process led by a committee of administrators, faculty members, parents, alumni, and students in the Spring of 2022, Jason P. Gallagher ’91, P’18, ’21 was enthusiastically named as Boston Latin School’s 29th leader on June 6, 2022. He had served 22 years within Boston Public Schools, the last 11 of which as the principal of the Harvard-Kent School in Charlestown, where as a team, they strove to meet the academic, social, and emotional needs of each child within a culturally responsive and robust learning environment. Under his leadership, the Harvard-Kent had been widely recognized for family and community engagement as well as for student growth and achievement, earning the prestigious EdVestors “School on the Move” Prize in 2019. Before that role, he served as an assistant director in the BPS Office of Special Education, and previously taught at the high and elementary school levels.

Of the 56 signers of the Declaration of Independence, five had been pupils of this school:

John Hancock, MASSACHUSETTS,

Samuel Adams, MASSACHUSETTS,

Benjamin Franklin, PENNSYLVANIA,

Robert Treat Paine, MASSACHUSETTS,

William Hooper, NORTH CAROLINA.

Commemorating those Latin School boys who fought to preserve their country in the Civil War, there stands in the first-floor corridor at the main entrance to the school a statue by Richard Saltonstall Greenough, Class of 1829. This statue, the gift of the graduates of the school, represents Alma Mater holding on her left arm a shield bearing the names of those who fell defending their country and extending in her right hand a laurel crown to those who returned from the conflict. Marble tablets on either side of the main entrance list the names of those who returned.

The Alma Mater statue, which originally stood in the large hall of the building that housed the school when it was located on Bedford Street, was the first — and for some time — the only memorial to the sons of Boston who served in the Civil War.

Latin School's service in World War I is memorialized by a bronze tablet on either side of the main corridor. The tablet on the right has inscribed upon it the names of those Latin School boys who died in service. The tablet on the left is in honor of the 480 alumni and undergraduates who enlisted in the U.S. Army or the U.S. Navy.

During the far-flung campaigns of World War II, 98 Latin School boys in the various branches of the United States armed service laid down their lives.