neighborhoods to the east. Daley’s commute brought him into
closer physical proximity with the blacks who lived across the railroad tracks, but it did nothing to break down the psychological
barriers that still separated him and his classmates from their black neighbors. De La Salle regarded its location in a black
neighborhood as an unfortunate trick of fate, and it made no effort to introduce its young charges to their neighbors. “The
school was surrounded by tenements and by low life,” a history of De La Salle, prepared by the school itself, states bluntly.
“It was a white school as an island surrounded by a black sea.” Daley traveled to De La Salle in a pack of his fellow Bridgeporters,
and quickly made his way out of the neighborhood when school let out. 24
De La Salle, founded by an Irish immigrant from the Christian Brothers Order named Brother Adjutor of Mary, had a highly practical
approach to educating the children of the Catholic working class. Brother Adjutor believed the best training for a young man
with few advantages was intensive instruction in business. De La Salle’s curriculum combined Catholic religious studies with
commercial courses, including typing, bookkeeping, and business law. The school had actual “counting rooms,” and other lifelike
replicas of business settings, for students to begin acting out the financial jobs they would one day hold. Daley continued
to be a diligent but unremarkable student. One classmate remembered him as “a hard worker ... maybe a little above average.”
Brother Adjutor’s educational philosophy worked well for Daley: the business skills he acquired at De La Salle were of considerable
help later in life, when his financial skills proved to be a critical factor in his rise up the ranks of the machine. Like
Nativity, De La Salle instilled the importance of unquestioning obedience. The Christian Brothers, imposing figures in long
black robes and stiff white collars, instructed with a strictness that at times crossed the line to brutal. “They were good
teachers,” one of Daley’s classmates recalled, “but if you got out of line, they wouldn’t hesitate to punch you in the head.” 25
De La Salle’s real strength was its extensive efforts to get jobs for its graduates. Most young Irish-Catholic boys coming
of age in places like Bridgeport in the early 1900s never made it out of the working class. But De La Salle opened up another
world, a white-collar alternative, for its students. As graduation neared, its faculty operated as a kind of Irish-Catholic
educational machine — mirroring the Irish-Catholic political machine — in which Brother Adjutor and other instructors drew
on their contacts in the business world to find jobs for the “Brother’s Boys.” Brother Adjutor’s reference letters were similar
to the ones precinct captains were writing in clubhouses across the city. Because of “the necessity of giving our students
a good start in life,” went one, “I have for many years past strenuously exerted myself to secure for them good positions
in the leading mercantile houses of this and other cities.” The school’s combination of commercial training and methodical
Irish-Catholic networking was a powerful engine for thrusting working-class boys into the upper echelons of the city’s power
structure. When Daley was elected mayor, he would be the third consecutive mayor educated at De La Salle. The school also
produced numerous aldermen, including two from Daley’s own graduating class, and many prominent businessmen. A commemorative
book boasted, with only some hyperbole, that “The battle of Waterloo was won on the playing fields of Eton” but “the business
leaders of Chicago were trained in the Counting Rooms of De La Salle.” As an adult, Daley would remember De La Salle warmly
as a place that “taught us to wear a clean shirt and tie and put a shine on your shoes and