
Christopher Sullivan, the former attorney for the city of Rutland, is led out of White River Junction criminal court in May after a hearing in his fatal hit-and-run case. Pool file photo by Eric Francis
However, his defense attorney did win a concession from that judge regarding what evidence he can present at the sentencing hearing.
Christopher Sullivan, 57, had argued through his attorney that Judge Theresa DiMauro should be disqualified from sentencing him because she had “prejudged” his case, pointing to comments she made at a hearing two months ago.
However, Judge Dennis Pearson, assigned to decide whether DiMauro should be disqualified, issued a ruling Tuesday afternoon denying Sullivan’s request.
Sullivan had his initial four- to 10-year sentence overturned in April by the Vermont Supreme Court.
The high court, in that same ruling, affirmed his convictions for drunken driving and leaving the scene of a fatality in the April 2013 crash in Rutland that killed Mary Jane Outslay, 71, of Mendon.

Judge Theresa DiMauro in White River Junction criminal court. File photo by Eric Francis
“The record here — even when considered in its totality and whether there is a pattern larger than the individual instances of allegedly disqualifying conduct — does not support an affirmative, and clear showing of bias or prejudice sufficient to overcome the presumption of judicial impartiality and fidelity,” Pearson wrote in his 12-page ruling.
Pearson said Sullivan’s recourse if he objects to DiMauro’s rulings is to appeal, even though he would have to wait until after the new sentencing.
The ruling is the latest twist in a case that has been working its way through the legal system for more than four years.
According to court records, Sullivan fled after hitting Outslay as she crossed a downtown street. He turned himself in a day later to police.
The Supreme Court overturned his original sentence, saying DiMauro should have allowed the defense more time to prepare testimony from a “mitigation” expert. By that point, Sullivan had already served about two years of his original prison term.
He was freed on $500,000 bail in May. Sullivan was city attorney in Rutland for many years. At the time of the crash, though, he was in private practice.
At issue in the latest filings are comments DiMauro made at a hearing in May after the sentence was overturned.
DiMauro had said at that time she would be limiting the new sentencing hearing to testimony from a “mitigation expert” regarding why Sullivan fled the crash scene.
Joshua O’Hara, a public defender representing Sullivan, has argued that additional evidence should be allowed, including how Sullivan has accepted responsibility for his actions and rehabilitative steps he took while in jail.
In a separate ruling issued Wednesday afternoon, DiMauro said she would allow O’Hara to present such evidence at the new sentencing hearing. She added that ruling in Sullivan’s favor in the matter will hopefully “avoid appeals on the issue and provide closure to the case.”
O’Hara, in arguing to disqualify DiMauro from the case, had also pointed to her comments from that May hearing that the chances Sullivan would have a time-served or substantially reduced sentence are slim.
“Such statements suggest the court has already discounted the likelihood that the evidence it hasn’t yet heard will change the Court’s mind,” O’Hara wrote.
Assistant Attorney General Ultan Doyle, who is prosecuting the case, had argued that DiMauro should remain.
Pearson issued his ruling based on written arguments by the two attorneys. No hearing was held.
Neither Doyle nor O’Hara could immediately be reached Wednesday for comment.
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