Raffles Institution (RI) is a "middle class" school that now largely caters to the affluent segment of society.
It also risks becoming insular, cocooned by the glowing list of academic and sporting achievements its students have racked up year after year.
These harsh words came from the school's own principal, Chan Poh Meng, in a speech delivered in front of hundreds of current and former RI staff and students.
Speaking at the school's 192nd Founder's Day ceremony on July 25, Mr Chan, who took over as RI principal at the end of 2013, said the school has suffered accusations of being elitist, a charge he did not deny.
Singapore, on the cusp of its 50th birthday, has been successful, building up a system that is admired the world over.
But fissures have erupted in the process, one of which is the faltering meritocracy that the country has been lauded for in the past.
"Our system of meritocracy is working less well than it used to, two generations in," he said.
Wealthier families have been able to give their children an edge through tuition and enrichment, leading to exams such as the Primary School Leaving Examination (PSLE) no longer being "the level playing field that they once were", he added.
For RI, the school is no longer how many alumni remember it to be in the past, with many students back then coming from diverse family and socio-economic backgrounds.
Today, the school "can no longer afford the comfortable illusion that RI is truly representative of Singapore", Mr Chan told the audience of 1,400 students, alumni, teachers and parents.
RI, widely considered the most prestigious school in Singapore, has long prided itself on its students' academic prowess.
"For a long time, we have measured our success by how high our PSLE cut-off and how low our L1R5 were. By how many Olympiads and competitions and tournaments we won... By the number of 'top' scholarships and places in the Oxbridge and Ivy League universities (students) secure," said Mr Chan.
But he questioned if the school's pride in such achievements may have had negative side effects, by becoming "insular - a school unto ourselves".
"A long period of conditioning means that we often fail to see elitism even when it is staring at us in the face," he said.
"RI has become a middle-class school - that is the current reality. What matters more now is what we do with this reality and this knowledge."
To this end, Mr Chan challenged students and staff to make RI a better school for Singapore, and not just for itself.
He set guiding principles for the school, emphasising that it must do its best to maintain the socio-economic diversity of its student population and reach out to the community with more purpose and heart.
"I put it to you that this is our wider duty to Singapore in 2015 and beyond - to serve as a social glue between parts of the community that have little or no contact with each other."
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