The teachers must pass by today or face the sack. But Wilfredo Laboy, the schools superintendent of Lawrence, Massachusetts, is questioning why he should have to pass.
Like most US states, Massachusetts requires all its teachers and school administrators to pass a literacy exam. Mr Laboy admitted inadequate revision, poor concentration and "grammar and punctuation" had proved his undoing.
The man brought in to lead Lawrence's troubled schools, which were plagued by financial scandals and poor test scores in 2000, has until December to make the grade.
But Mr Laboy said: "I'm trying to understand the congruence of what I do here every day and this stupid test," he told his local paper, The Eagle-Tribune. He described his failures as "frustrating" and "emotional" and laid particular blame on the fact that Spanish is his first language.
Mr Laboy is a native of Puerto Rico, and said: "English being a second language for me, I didn't do well in writing. If you're not an English teacher, you don't look at the rules on a regular basis."
Kathleen Kelley, president of the Massachusetts Federation of Teachers, was unimpressed.
"A superintendent of a school system is the educational leader. If we are demanding high standards for students and teachers, the person who leads them should meet the same standards," she said.
Teachers who failed the test faced summary dismissal before the union intervened, she added, and most had passed the written component which tripped up Mr Laboy, and stumbled only on the oral part.
And while the teachers are at risk of losing their jobs today, a 3 per cent rise last week took Mr Laboy's salary to more than $156,000 (pound;104,000).