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To completely understand why a former school superintendent siphoned more than $100,000 from a struggling north St. Louis County district, prosecutors say, you must also understand his gambling.

Henry P. Williams liked the slots.

Williams gambled the day he signed his first employment contract with the district. He gambled before or after school board meetings. He often gambled 20 days or more per month.

In fact, over the five years he led Riverview Gardens School District, Williams gambled more than 900 days - nearly 190 days a year - and lost as much as $176,000, according to court records just made public.

All the while, the 8,000-student district was falling into economic and academic failure.

Williams, 67, was driven out of the district almost two years ago after being accused of funneling more than $100,000 in school money into a personal life insurance fund, understating his income and double-dipping on district travel reimbursement. He pleaded no contest in September to two counts of felony theft and three counts of tax fraud.

Early this month, Williams was sentenced in St. Louis County court to 30 days in jail and ordered to pay $102,724.87 in restitution to the district.

He would not discuss his gambling publicly, and rejected multiple interview requests.

But court documents made public after Williams' sentencing reveal what prosecutors believe, in part, motivated his thievery.

They describe a man who repeatedly tapped into his district-funded life insurance policies, and gambled away similar amounts at the casinos - almost entirely on slot machines.

"He stole from the kids to support a habit. That's not right," Riverview Gardens School Board treasurer Selena Melton said. "At least we're getting some of the money back. That gives me some satisfaction."

Puzzling Finances

St. Louis County prosecutors subpoenaed district records in early 2006, following police tips, and soon realized that Williams was stealing district funds.

But what prosecutors didn't immediately know was why he wanted the money.

As superintendent of Riverview, Williams made $135,000 his first year and $160,000 his last.

His contract also stipulated extras: a life insurance policy, $3,000 toward other insurance, a car allowance, mileage, 50 vacation and sick days, and $15,000 to $25,000 each year for his tax-sheltered annuity.

It was Williams' management of that annuity benefit that raised suspicions.

He asked district workers to send the checks not to a tax-sheltered annuity, but to his whole life insurance policies at The Guardian Life Insurance Company of America. And, as soon as the district had deposited the money, Williams was borrowing against those policies, investigators said. He asked the district to pay the policy premiums, plus the interest on the loans.

By the end of 2005, he had $180,000 in outstanding loans against his Guardian policies, according to court records.

Where was that money going?

One place, investigators discovered, could have been to cover back taxes. According to liens filed with the county, Williams still owes nearly $250,000 in federal taxes. None show they've been paid off, and one, for $24,915, was just filed in November.

Then, on a tip, the prosecutor's office also checked to see if Williams was spending money at local casinos.

'7 Stars Club'

The court records begin with a printout from the Ameristar Casino in St. Charles.

In January 2002, just a few months before Williams started as superintendent in Riverview Gardens, casino records subpoenaed by prosecutors show he gambled 21 of 31 days. In February, he gambled 27 of 28 days.

He began work that fall, and continued gambling.

In 2003, records show Williams began frequenting a second casino, Harrah's St. Louis, just downriver in Maryland Heights. His yearly visits increased a bit.

In 2005, Riverview Gardens was in tumult: Williams declared teacher morale at its lowest. More than 700 students marched on the district office after a popular principal was fired. Parents, fearing financial mismanagement, demanded a state audit. Graduation rates, attendance and test scores all dipped.

That year, Williams visited either Ameristar or Harrah's more than 220 days, or nearly two-thirds of the year.

There is little in the documents to suggest Williams was spending school hours at the casinos. Indeed, some school officials now say he was a present administrator who worked a full week.

Still, successful school districts often have leaders who work far more than 40-hour weeks, said William Rebore, chair of the educational leadership department at St. Louis University. "A great deal of information has to flow through the superintendent and the superintendent's desk," Rebore said. "Superintendents who are unsuccessful are those who do not spend sufficient time on the job."

By November 2006, the last month of records held by the court, Williams had visited Ameristar and Harrah's more than 930 times over five years, lost $42,529 in total at Ameristar and $133,704 at Harrah's, and spent in excess of 1,100 hours at Harrah's slot machines alone.

That means, on average, he lost $122 every hour he gambled at Harrah's.

It is possible, industry insiders say, those totals could have been inflated by "free" money the casinos sent to Williams as incentives. However, they say, it's unlikely incentives would have represented a large chunk of the losses.

Representatives from the casinos wouldn't clarify the documents or discuss generalities.

But there are other hints as to Williams' spending.

The court records show he played high-dollar slots with $2,500, $5,000 or even $10,000 payouts, in rooms that now have signs warning gamblers: "This area is reserved for high limit guests only."

The records also show that Williams earned thousands of dollars in freebies, far beyond those won by recreational gamblers. He got hotel rooms, cash back, and meals at virtually every eatery at Harrah's.

But even more so, Williams' account at Harrah's was specially marked. It was tagged "7 Stars Club" - the rewards tier reserved only for elite gamblers, those who played at least $500,000 on slots in one year.

The End

The Riverview board removed Williams from office in March 2007, after state and Post-Dispatch investigations revealed many transgressions: District money directed to his daughter, girlfriend and her family. Thousands of school dollars spent on his office art, cash advances, theater tickets and trips - to London, South Africa, and many U.S. cities.

Worse, Williams left the district in ruins. Riverview savings had dipped from $12 million to less than $2 million, and academics had sunk to the point that the district met just three of 14 state accreditation standards.

Most district leaders say that they are moving on, and declined to discuss Williams and his legacy.

But Riverview employees report seeing Williams at the casinos since he left the district.

One said she saw him a few months after he was fired, in what she called the "high-rollers'" room.

Another said she saw him at the slots, with a woman.

And district custodian Roy Mullen said he saw Williams this winter.

"I was just looking for some of my friends," Mullen said. "I come around the corner and say, 'Holy cow!' I can't believe who I see sitting there."

It was on the weekend, Mullen said, just before Williams was set to be sentenced.