There is no question that Tom Freston can afford to give his children the best education money can buy. The former Viacom CEO was among the country's most richly paid TV executives and got an $85 million severance deal when he was forced out of his job last year.

Nevertheless, he is a combatant in an unlikely legal fight: On Monday, the U.S. Supreme Court will consider whether taxpayers should have to foot the bill for his son's expensive private school education.

The family and the city of New York are at odds over the schooling for Freston's son, who was diagnosed with learning disabilities in the late 1990s.

The family's solution was to send the boy to the Stephen Gaynor School, a top-notch but expensive Manhattan academy for children with learning problems.

Freston also followed a path being taken by an increasing number of parents of special education students: He asked the city's public school system to pay his son's tuition.

Federal law demands such payments when a public school system is unable to properly deal with a student's disability, but in this case New York City said it could do the job. It recommended that the boy attend the city-run Lower Laboratory School for Gifted Education.

Freston sued. The city paid $50,000 in tuition over two years before deciding, after a review, to go to court.

The issue before the Supreme Court has nothing to do with the family's wealth, or the morality of a millionaire asking a cash-strapped school district for help with an ivy league-sized tuition bill.

Instead, New York City is arguing a technicality. It says that, under federal law, special education tuition aid is only available to children who actually enroll in public schools — not to lifelong private-schoolers who have never used the public system.

Attorneys for Freston and several advocacy groups say federal rules don't require such an enrollment.

"The danger of making parents try out the school district's program first, even if it's not an appropriate program, is that students who need early intervention waste critical time," said Gary Mayerson, a lawyer who works with the group Autism Speaks.

"If my child can't swim, and the school district's plan is to throw him in the deep end of the pool, I shouldn't have to allow my child to drown to prove that the district's plan is ridiculous."

Leonard Koerner, chief appeals lawyer for New York City, said parents should be required to give the public system a shot, even if only a brief one, before they can appeal for an outside placement.

An attorney for New York's Education Department, Michael Best, said a court victory for the city would ensure that taxpayers don't pay private school tuition for parents "who never had any intention of enrolling their child in the public schools."

Nationwide, the number of special education students placed in private schools at public expense has risen steadily, from about 52,012 pupils in 1996 to 71,082 in 2005, according to the U.S. Department of Education. Overall, however, the number of such placements remains small — just 1.1 percent of the country's 6.1 million special education students.

In New York, a growing number of parents have been exploring a private-school option. During the 2002-2003 school year, the city received 3,908 tuition reimbursement requests, Best said. By the 2005-2006 school year, that number had jumped to 4,804.

Parents who are denied aid may place their children in a private program and sue for tuition, but they run the risk of being stuck with the bill if a court doesn't agree with them.

Freston's lawyer, Paul G. Gardephe, said his client did not want to be interviewed, but issued a written statement in which Freston said he wasn't pressing the case for personal gain.

"Children with special education needs have a right, without jumping through hoops, to attend schools capable of providing them with an education that accommodates their individual needs regardless of their family's financial means," Freston wrote.

He added that the family donated the money it got from the city to create a special education learning center.

However the case comes out, it has had one happy ending: Freston said his son thrived at Gaynor and has transferred to a mainstream school.