Superintendent of City Schools
His family was poor, but he distinguished himself in school, first as a student and eventually as the creative and persistent leader of the largest city school district (New York) in the U.S. where this child of immigrants brought new programs to hold adults accountable to improve their students.
FAMILY BACKGROUND
Anthony Alvarado (AA) was born in New York City, raised in the South Bronx area. His father, a Cuban immigrant, was the manager of a dress factory. His mother, born in Puerto Rico, was a homemaker.
EDUCATION
AA was a dedicated student who made the most of his opportunity to attend a private college prep school (Fordham Prep) in the Bronx. He then earned a Bachelor’s degree in English from Fordham University, followed by a Master’s degree in the same subject from Fordham.
FIRST ADULT JOB DONE WELL LEADS TO PROMOTIONS
Typical of many first-time teachers, AA’s first opportunity along the career path as an educator was to serve as a substitute teacher. Next, he was hired for several administrative posts at the Board of Education’s Brooklyn headquarters, where he was able to demonstrate to the overall district leadership his willingness to learn the overall district policies and procedures and offer good suggestions for how the policies could best be implemented to be helpful to teachers and students.
Accordingly, AA was appointed by the city’s overall Board of Education to be Superintendent of District 4, a predominantly Black and Hispanic area. In this post, AA first became known for challenging the board’s bureaucracy but until he had more senior authority, wisely avoided directly speaking out against his superiors. Later, when appointed overall Chancellor (another word for overall Superintendent), AA openly stated that district bureaucracy had constrained individual initiative. As AA stated at his induction ceremony, “There is always the question, Can the octopus so enmesh you that there will always be an arm around you, tugging you from the direction you want to go? The octopus is the system. I’ll walk around with a pair of shears in my back pocket. Whenever I see a tentacle, I’ll take it out.”
Throughout his different schools’ administrative jobs, AA accomplished much, including:
- Advocated training teachers more rigorously.
- Promoted raising the expectation of success for pupils and teachers alike.
- Established min-schools devoted to specific subjects, attracting residents from elsewhere in the city to one of its poorest neighborhoods (Editor’s note – in Philadelphia, this concept is known as a ‘magnet’ school).
- He recruited experts from New Zealand and Australia, the two English-speaking nations with the highest literacy rates.
- He held principals accountable not just as school managers but also as instructional paragons.
- He slashed the overall school district’s central staff.
- Reading scores rose and some middle-class families that could afford private schools returned to the district’s public schools.
AA’s education philosophy held adults responsible for the failure of kids. As he stated (in an interview with a local PBS program, “Making Schools Work”), “What has tended to happen in American public schooling with poor kids, is that expectations for their basic academic performance are decreased in contrast to middle and upper economic class kids. This must not be allowed to happen and as long as it does, the social and economic divisions among people will persist if not increase.”
CHALLENGE – BUDGET LIMITATIONS
AA was criticized for allowing the district(s) he was leading to exceed their respective budgets.
AA’s defense: “Let’s spend money for schools and teachers rather than warehousing aimless children in jails.”
CHALLENGE – MANAGING PERSONAL FINANCES
Only through a random gun arrest of an aide who had lent money to AA, did AA’s bad judgment regarding his personal finances become known to the public. When the aide was arrested for firing a gun through a neighbor’s window for reasons never known – with no involvement by AA – police investigators discovered two uncashed checks totaling about $10,000 payable to the aide by AA as repayment for personal loans.
AA eventually admitted his tangled personal finances, which were stretched because he was supporting two daughters from a previous marriage. Investigators determined that AA had received $80,000 in loans from his school district subordinates. While there was no crime involved (the subordinates received no benefits from loaning money to their boss – for example, potential benefits such as job promotions or unearned overtime pay or extended job vacations – none of which was ever found), AA admitted to his very poor judgment by soliciting the loans and then he resigned as Superintendent, acknowledging his “horrendous” judgment but claiming that he had “never used public funds or the public system for personal gain.”
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(Editor’s note – Why is it a very bad idea to ask employees to loan their boss money or to buy something unrelated to their job, from their boss? The basic reason is that having any personal (nonbusiness) relationship between a boss and an employee – other than acceptable minor courtesies such as occasionally exchanging a minimal cost birthday gift or being treated to lunch – changes the dynamic of their business relationship. Every business requires that supervisors be able to honestly evaluate and motivate employees for the sole benefit of the business. Similarly, a supervisor should be willing to listen to constructive comments from an employee about how the business could be better managed. But if the supervisor owes (any amount of) money to the employee, the supervisor cannot honestly assess the work of the employee.
Two personal examples from the Editor: As a supervisor, I never brought our daughter’s Girl Scout cookies to the office for sale; I brought the cookies to share but would never accept any payment for them. Earlier as a junior employee, I bought a used car from a supervisor. It turned out there were never any problems with the car but how can a supervisor and an employee objectively determine a fair price between themselves and what if there had been undisclosed (did the supervisor know but not say?) engine issues requiring expensive repairs?
Issues involving exchange of money between supervisor and employee are separate from even more serious problems within the toxic mix of office romance or sexual harassment between a supervisor and an employee – neither should ever be involved at the office. Consequences range from loss of employment and reputation to criminal charges.)
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Three years later, AA felt vindicated professionally when he was hired by the same city school district to be one of their superintendents for a different school district.
Eventually, AA was recruited to be Chancellor of instruction, the No. 2 position, for the San Diego school district. There he instituted coaching for teachers and increased student instruction in reading and writing. But he was viewed as an outsider and became a lightning rod for political opposition to most reforms.
AA was later a professor of education at Stanford University in Palo Alto, California and served on the board of Educational Testing Service, the nonprofit organization that develops and administers standardized testing across the U.S.
CAREER SATISFACTION
During his years as an education leader for a public school district of mostly Black and Hispanic heritage, the number of district children who could read at or above grade level rose in three years from 25% to 48%. The district’s rank in reading scores among the city’s 32 community districts rose to 15th from 32nd.
Education colleagues called AA “a dynamic and incredibly creative educational leader.” Another said, “He not only had important, innovative ideas, but he also was able to implement them. He was an inspirational force who turned things around in two large community school districts.”
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This career story is based on an obituary written by Sam Roberts, published by The New York Times newspaper on January 10, 2024, plus internet research.

