Paul Callahan

Growing a thriving business while enjoying a satisfying career and building an impeccable reputation in Jamaica Plain, Paul Callahan never forgot his faith and his responsibilities in living it. Callahan’s Men’s Shops served thousands of Roxbury and Jamaica Plain customers, including several prominent politicians and sports figures, through The Great Depression, the war years and the post-war social upheavals in Boston. They were respected members of their Roxbury and Jamaica Plain communities for 75 years.

Special thanks to John Lovett who suggested this story and participated in the interview on November 6, 2014. Kathy Griffin provided production assistance.

Paul Callahan

Paul Callahan was born on May 22, 1931 at 10 Roseway Street, Jamaica Plain. Paul’s parents, Edward J. and Mary E. Callahan, had family roots in Ireland and Germany. Edward was born in Jamaica Plain in 1896 and Mary in Olneyville, Rhode Island, in 1898. Paul lived in the Roseway Street house with siblings Edward Jr., Donald and Gloria until his marriage in 1964. Paul’s family owned and operated two men’s clothing stores in Roxbury and Jamaica Plain.

Among many school memories, one of his earliest is of the German airship, Hindenburg, flying over Boston on May 6, 1937 on the way to its fatal crash in Lakehurst, New Jersey. His second- grade class at the Curley school was released to see the ship as it passed overhead. Paul remembers thinking it was very big and very low as it flew slowly over Jamaica Plain.

Hindenburg over Boston, May 6, 1937

After the Curley School, the Agassiz School, and the Curley School again, he graduated from Jamaica Plain High School as the 1950 Class President, Captain of the football team and the acknowledged best-dressed kid in school. His yearbook entry said his life’s goal was “to never grow old.” Decades later, this class president would keep his class young by organizing many reunion trips to Maine and regular reunion luncheons at a local restaurant.

Paul’s football career at Jamaica Plain High School included playing in the first high school game at White Stadium, against South Boston High, on the evening of September 28th, 1949. Paul Callahan, President, Jamaica Plain High School Class of 1950 The coin-toss for the game was done by Mayor James Michael Curley. Up until this time, regular-season games were played at various high school fields and playgrounds around the city, only a few of which had lighting. The new White Stadium, with its clean new locker rooms, tunneled entry to the beautiful grass field, and unlimited hot showers was like playing in the NFL! William Bond, the longtime and much-loved Jamaica Plain High School teacher and coach, had promoted Paul off the bench when the football team’s Center, and later assistant coach, Adam Mroz, was injured. Paul kept the Center’s job for the rest of his playing days.

Paul served in the U.S. Army from 1952 to 1954, stationed at the United States Military Academy at West Point, New York. Paul and his regular-Army troops provided support services for the cadets including medical care, food service, the marching band, and military police protection. Paul was garrisoned on the West Point campus for the length of his service, and despite his lack of typing skills, he was assigned the Company Clerk’s duties!

When discharged in August 1954, Paul started at Suffolk University the following month and graduated in 1959 with a Bachelor’s degree in Business Administration. He had worked part-time in the family business since 1940 and upon graduation went to work, full time, at the Dudley Street store, hoping to earn more than the 10-cents-an-hour he received in 1940 at the Centre Street store!

White Stadium dedication program

He would later manage the Jamaica Plain store for twenty years, leaving a permanent mark on the store’s neighborhood, thousands of satisfied customers, hundreds of uniformed young athletes at St. Thomas Aquinas Parish, and many grateful families who were treated with dignity and respect by the church-related, but privately-funded charity Paul has managed for nearly 45 years.

Paul has lived in the same house on Dunster Road for 42 years. His neighbors there include the Paget family, longtime owner/operators of the Boston Swan Boats, which are stored in their back yard.

79 Dunster Road

Callahan’s Men’s Shops

When Paul’s father, Edward Sr., decided at age 23 to go into the men’s clothing business, he looked for a location where plenty of foot traffic would inevitably bring in business. In 1918 he found the perfect spot at 294a Centre Street, opposite the Thomas G. Plant shoe factory. Employment at Plant’s topped 4,000 people at peak, many of whom were young Irish and German immigrants.

Just a year later, in 1919, Edward opened a second store at 155 Dudley Street, Roxbury, near the corner of Harrison Avenue and the famous Hibernian Hall at 184 Dudley Street. Built in 1913 by The Ancient Order of Hibernians, Hibernian Hall was the center of Boston’s Irish social life. For many years, especially after the war when five Irish dance halls (the Hibernian, the InterColonial Club, the Dudley Street Opera House, the Rose Croix and Winslow Hall) were clustered at Dudley Street, this location provided the kind of foot traffic Edward wanted. Young Irish working men seeking to improve their appearance and social standing flooded the area. The boom years for these dance halls ran from the 1940s to the 1960s. Dudley Street back then was called “the closest parish to Galway.”(1)

John Lovett recalled that his father had danced at Hibernian and remembered the Callahan’s store nearby. Later, John’s father’s brother-in-law, John Kelly from Cork, Ireland, ran Hibernian Hall. That led to a job for John in the cafeteria at the famous dance hall.

Dress codes did not have to be enforced at these lively Irish dance halls because everyone came in their Sunday best. Where better, then, for the men to get decked out than at nearby Callahan’s? In addition to the dance hall attractions, the Dudley Street area was teeming with people coming by streetcar and the “elevated” to shop at Ferdinand’s Furniture store, Folsom’s Market, Timothy Smith’s Department Store, Dutton’s and Hovey’s stores, Blair’s Foodland, and the many specialty shops springing up along Washington Street, including several competing men’s clothing stores.

One of the features of the Dudley Street Callahan’s store was that a tailor, above the store, could cuff a pair of pants in five minutes. This no-charge service, along with the usual suit and jacket alterations, was just a few of the reasons clothing flew out of the store to a widely-diverse, and extremely clothes-conscious, clientele. Callahan’s clients included Mayor James Michael Curley, Governor (and later Secretary of Labor) Maurice J. Tobin, and many other Boston-area politicians, as well as George Scott of the Red Sox and Sam Jones of the Celtics.

In 1928 the store at 294a Centre Street was moved to 362c Centre Street at the corner of Forbes Street, opposite the Blessed Sacrament Rectory. This location added the church and Hyde Square shopping traffic. It was perhaps the “classiest” store in the area at that time, as has been noted by other Jamaica Plain Historical Society writers.(2)

In 1959, Paul moved to the Dudley Street store, replacing his brother Donald who left to become an Air Traffic Controller. Edward Sr. died in 1967, and Paul’s brother, Edward Jr., took over the business at the 362c Centre Street store. Paul was managing the Dudley Street store at the time.

In 1968, Mike Williams, fresh out of Dorchester High School, was hired at the Dudley Street store. He remained an outstanding Callahan’s salesman and family friend for 25 years, eventually managing the Dudley Street store in 1985. When the Dudley Street store closed in 1992, Mike took an administrative job for the City of Boston, where he works today.

In 1969 the family remodeled the Dudley Street store and won an award from the Roxbury Merchant’s Association.

In 1978, the final move of the Jamaica Plain store saw the store at 362c Centre Street, at Forbes Street, relocated to 730 Centre Street, at the corner of Harris Avenue.

730 Centre Street then and now

In 1983, Paul’s brother, Edward Jr, retired. Paul then moved to the 730 Centre Street store and took control of the business.

In November 1992 Callahan’s Men’s Shop was honored as an Outstanding Business by the Jamaica Plain Business and Professional Association.

1993 saw the end of Callahan’s 75-year run when Paul retired after 53 years in the family business. Both stores had survived the sharp decline in race relations and increases in crime in the 1960s and 1970s, and there were a couple of unpleasant incidents in the Jamaica Plain store. Overall, however, Paul says that the stores’ reputations and race relations remained very strong in those turbulent times.(3)

This 1995 watercolor by an artist named T. Carey and the photograph capture the essence of the last store at 730 Centre Street. A restaurant currently occupies the site.

730 Centre Street watercolor by T.Carey

About Men’s Clothing

Small retail clothing shops relied on experienced wholesale salesmen to keep them abreast of evolving fashions. Paul remembers these salesmen arranging visits to clothing manufacturers in Boston to see the new styles and to pick up orders. Those manufacturers included Dainty Dot Hosiery, Cooper’s Underwear, Joe Price Neckwear, Al J. Samuels Clothing (suits), the Cable Raincoat Company, Joe Winer Caps and the distributors of Swank and Hickock leather goods (belts).Coupled with awareness of the current styles was the knowledge of their customers’ preferences and tastes, which varied greatly from store to store over the years. The style preferences in Dudley Street were markedly different than at the Jamaica Plain store just a few miles away, so it was important to buy merchandise the different clientele would prefer, and to never mix the two stores’ inventories.

Callahan’s suit sale

While both stores sold a full line of men’s clothing, the biggest seller, and the thing that built Callahan’s stores’ reputations, was men’s hats. Callahan’s was one of Boston’s largest hat retailers. Back in the day, every man would have a couple of good fedora hats to match his topcoat, suits or other seasonal outerwear. These fedora or “soft” hats would also be seasonal, i.e. of a material suitable for the weather. Some readers may remember one well-known Boston department store, Raymond’s on Washington Street, founded in 1870, whose slogan was: “Raymond’s, Where You Bought the Hat!” In downtown Boston, the best men’s stores, and style setters, were Brooks Bros. and Leopold Morse Company.

Leopold Morse Co., Boston

Callahan’s hat by Stetson Company


Hats were guaranteed

There were hundreds of designs for men’s hats made by the major hat-makers including Stetson, Adams, Bollman, the Picayune Hat Company, and others. These large manufacturers would also custom-build hats to a retail store’s design. The hats could be made of wool, rabbit fur, beaver fur or velour. This gave the retailer a distinctive hat style that could be labeled with that store’s name. Callahan’s hats were made exclusively by Stetson Company and each was embossed on the band with Callahan’s Trademark. Callahan’s was the largest Stetson hat outlet in Boston for a number of years. The only downside to customizing the hats was the long delivery time.

Callahan’s Trademark

Variables in hat design included base material and color, brim width, crown height, and the band location. Paul’s father, Edward Sr., designed a “Secret Hat” and received a certificate documenting the Callahan Trademark for the hat. Edward then ordered a bright red neon window sign announcing “The Secret Hat,” which, sadly, was lost in one of the store’s moves.

Trademark certified by the Commonwealth

When a customer bought a hat, his initials were embossed at the rear of the band, using the stamping device shown. If the initials were placed at the front, the customer would have his initials impressed on his forehead! A hat could also be stretched for better fit using the stretching device.

The embossing, or labeling, machine

The hat stretching machine

The well-known brand of Adams Hats was widely advertised but, because it was made of wool, it didn’t fare well in the rain. The Stetson hats were made of either fine rabbit or beaver fur. Paul has a collection of 30 of these Stetson/Callahan hats, some nearly 40 years old, which still look new. Among his collection are a ceremonial hat and its metal case which belonged to the Sherriff of Dublin, Ireland, in 1905.

Dublin Sherriff’s hat

Neckties were a big seller at Callahan’s, with prices at 55 cents, 65 cents, and the high end reaching $2.50 each. They were hung from boards suspended from the ceiling to be easily seen when matching with the customers’ suits, jackets or shirts. Hand-painted ties were popular and every man had at least one of those to brighten his wardrobe.

Van Heusen and Arrow were the big names in shirts. The shirts were never displayed but were sold, unwrapped, out of boxes on the shelves that kept the stock clean. No cellophane or plastic bags were used in the old days. One shirt sale at $1.95 guaranteed steak for supper that night for the Callahans! Van Heusen button-on collars were also popular.

Van Heusen collars

Advertising and seasonal window displays were vital parts of Callahan’s success. Because it was considered an art, a professional window dresser, Bernie Schwartz, was hired for the twice-a-year window displays. Bernie’s work won “best window” contests for several years.

Callahan’s newsletter


Family life

Paul married his sweetheart, Jane (Wilson), in 1964. Jane was born in 1935 and had lived on Mission Hill at the corner of Parker and Tremont Streets. She graduated from Blessed Sacrament High School in 1954. They had two girls, Nancy and Paula, a son, Paul, and eight grandchildren in 49 wonderful years together before Jane went to her rest in 2013. The family home on Dunster Road is decorated with many of Jane’s beautiful needlework pieces and paintings that she carefully selected for their home.

Around 1990, Paul began donating the baseball and basketball uniforms for the St. Thomas Aquinas CYO teams. They were worn with no hint of who provided them. That is, no sponsor’s name ever appeared on any of them.

For decades Paul has served as an usher at St Thomas and for 45 years he has managed the main charity of the parish, the St. Vincent de Paul Society. The Society is totally supported by parishioners’ donations and fund-raising trips that Paul has planned, organized and led for parishioners and other donors. The charity provides much-needed support for as many as 20 families every week.

Paul Callahan and John Lovett, November 2014

Paul and John Lovett fondly remember Sister Jeanne (Gribaudo) CSJ, originally from Roslindale, a member of the Order of the Sisters of Saint Joseph, who joined St. Thomas Aquinas Parish in the early 1990s as a Pastoral Associate. In that role she had a positive impact on all aspects of parish life, and was largely responsible for making the parish grow. The Pastor, Father Thomas, initially wondered how long their personalities would work together, but they did for many years.

Paul and John were proud to see Sister Jeanne coordinating the late Mayor Menino’s funeral Mass. Sister Jeanne had worked for the Mayor as a dollar-a-year advisor on youth issues. Mayor Menino, who was John Lovett’s classmate in the St. Thomas Aquinas High School class of 1960, dubbed her “Sister Relentless” for her tireless efforts to get the city to allow her to use Boston public school gyms for basketball games she organized in the early 1990s. Sister Jean is now posted to St. Agatha’s parish in Milton and teaches at Merrimack College in North Andover. She remains close to the Menino family.

St. Thomas Aquinas church, 1940s

John Lovett reports an interesting side note from Mayor Menino’s funeral when President Clinton was seen chatting with a Security Officer just after the service. The officer was wondering what the President and Mayor Menino were chatting about in the nice photo of them on the wall at Doyle’s Café? President Clinton replied, “We were talking about managing our weight!”

Community recognition

In a surprise ceremony on March 24, 1995, the corner of Centre Street and Harris Avenue was named Callahan Plaza. Paul was set up for the surprise under a pretext to help his son-in-law at his office nearby. He was then led outside to a cheering group who unveiled the new sign honoring the Callahans. Later that same day, another surprise was sprung by his daughter as Paul found himself guest of honor at a large gathering at the Footlight Club on Eliot Street. He was simultaneously lauded as a genuine good guy and roasted with more than a few embarrassing stories Paul had hoped were long-forgotten. The late Mayor Thomas Menino was also present to lend his testimonial to Callahan’s long-time service to Jamaica Plain and Roxbury.(4)

Callahan Plaza, Centre Street at Harris Avenue


Never comfortable staying idle, Paul and Jane got into the antiques business by shrewd buying at local auctions and then retailing through consignment antique shops. They had a booth in a large store in Wrentham which has since folded and left Paul with large left-over inventory which will probably be sold on-line.

Paul also has a horticultural bent, taking cuttings from his mother’s old plants and thus perpetuating them. He has about 55 house plants and from time to time offers them for sale in an honor-system sidewalk sale which he proudly says has never once been abused. He also maintains a healthy and productive vegetable garden decorated with old Jamaica Plain street signs.

Looking back …

Despite the eleven-hour, six-day work weeks, along with the typical small-business staffing and financing problems, and in later years, robberies and shoplifting, Paul has never regretted his choice of a career. He always remembered his father’s devotion to the family business which motivated him for 53 very happy years as Jamaica Plain’s premier haberdasher, while always finding time for his own family and his church.

By Peter O’Brien, November, 2014


1. Book: Susan Gedutis, 2004, “See You at the Hall: Boston’s Golden Era of Irish Music and Dance”

2. Jamaica Plain Historical Society: Richard Goolsky’s 1940s Jamaica Plain, Part 3.

3. Jamaica Plain Gazette, February 24, 1995

4. Jamaica Plain Gazette, April 7, 1995