A Texas convict with a lengthy criminal history was executed Tuesday evening for fatally shooting a man and raping the slain man’s fiancee during a home break-in more than 22 years ago.

Rickey Lynn Lewis already had been in and out of prison five times in less than seven years when he was arrested three days after the killing of 45-year-old George Newman and attack on Newman’s fiancee in 1990 at their home in a rural area of Smith County, about 90 miles east of Dallas.