The salaries and benefits of headmasters of private prep schools have been rising nationally and in the Bay State. The Globe checked federal tax records to see who receives the most. Below are the schools and the 2003-04 figures on headmaster pay and benefits
| Head of school | Salary | Benefits | total |
| Barbara L. Chase, Phillips Academy, Andover | $280,017 | $133,991 | $414,008 |
| Robin Robertson, Milton Academy, Milton | $310,000 | $29,771 | $339,771 |
| Eric Widmer, Deerfield Academy, Deerfield | $307,000 | $31,700 | $338,700 |
| Robert P. Henderson, Jr. Noble and Greenough School, Dedham | $257,000 | $50,548 | $307,548 |
| Bruce Shaw, Shady Hill School, Cambridge | $229,160 | $32,092 | $261,252 |
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