He was an assistant attorney general and chief of the Massachusetts Criminal Division from 1963 to 1965, thereafter returning to private practice in Boston until 1973.

In 1978, the judge refused to hear an after-hours case seeking to permit the New Hampshire governor to fly flags at half staff on Good Friday, to "memorialize the death of Christ".

[2] Skinner returned to public attention in 1986 during the civil trials for contamination of the Woburn wells and water supply, first by imposing a gag order on the plaintiffs, preventing them from making public comment about the case;[3] and then by throwing out the jury's guilty verdict against W. R. Grace on the grounds that he found some of their answers to the questions about the hydrogeological data to be confusing.

[4] Skinner was portrayed by John Lithgow in the 1998 film A Civil Action about the Woburn case.

In 1988, Skinner notably considered a plan to gradually release certain inmates prior to the completion of their sentences, in an effort to relieve overcrowding in county and city jails.