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Three men pleaded innocent Tuesday in Cook County Circuit Court to the 1988 contract killing of a Palatine Township woman who was shot five times in the head outside her apartment building.

Those entering the pleas of innocent in the Rolling Meadows Courthouse were Joseph Rinaldi, 33, of Oak Forest; Chicago Firefighter Michael Permanian, 32, of Chicago; and Ronald Kliner, 32, of Des Plaines. All three men are being held without bond in Cook County Jail.

Prosecutors charge that Dana Rinaldi, 28, was killed Feb. 18, 1988, as a result of a contract killing arranged by her husband, Joseph, who later collected $130,000 from two life insurance policies on his wife.

Rinaldi allegedly hired Permanian and Kliner, boyhood friends, to carry out the killing because he was unhappy with his 8-year marriage to Dana Rinaldi.