Alan Simpson, an old school moderate Republican senator who helped craft major U.S. immigration reform in 1986 and made friends across the aisle, died on Friday in Cody, Wyoming, his family said in a statement.

Former U.S. Senator Alan Simpson has died at the age of 93, according to a statement from his family and the Buffalo Bill Center of the West. Simpson, who represented Wyoming, died early Friday after struggling to recover from a broken hip in December.

Pushing the 1986 immigration reform bill through Congress — his major legislative accomplishment — was like “giving dry birth to a porcupine,” he quipped.