Judicial Record
In 1990, Whittemore was elected to the bench of the Hillsborough County Circuit Court in the Florida Thirteenth Judicial Circuit, and remained on the court until 2000. He was named the 1998 Jurist of the Year by the Hillsborough County Bar Association, and Outstanding Jurist of 1999 by the Florida Bar's Young Lawyers Division. After recommendation by both of Florida's U.S. Senators, Democrat Bob Graham and Republican Connie Mack III, he was nominated by President Clinton to a new seat in the Florida Middle District Court on October 20, 1999. Whittemore was confirmed unanimously by the United States Senate on May 24, 2000, and received his commission the following day.
On June 4, 2001, Whittemore ruled against Rolando Viera, a Cuban baseball pitcher who was attempting to enjoin Major League Baseball from including him in its amateur draft so that he could instead be a free agent. Viera had claimed that the MLB draft was discriminatory because it had a different residency requirement for Cubans, but Whittemore decided that whatever financial loss Vierra suffered from being subject to the draft did not satisfy the federal injunction requirement of irreparable harm. Viera was picked by the Boston Red Sox that same week in the seventh round of the draft.
Whittemore presided over the criminal trial of Gerald and Betty Payne, the founders of Greater Ministries International Church. Over $450 million was bilked from church followers in the Paynes' fraudulent investment scheme, which was billed as one of the largest Ponzi schemes in U.S. history. Whittemore sentenced Gerald to 27 years for conduct he called "absolutely despicable." Betty was sentenced to over 12 years, which was increased from what Whittemore initially considered after she repeated a claim they were the innocent victims of government persecution and their religious freedoms were being violated. "It's one thing to have blind faith," Whittemore told her. "It's quite another to cast yourself as a martyr for no apparent good. I just deliberated a matter that you could serve 33 months less. What you've just done is throw that right back in my face."
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