[3] Wolski received a Bachelor of Arts in history and a Bachelor of Science in economics from the University of Pennsylvania in 1984,[2] and thereafter served as research associate to a supply-side economist at the Center for Strategic and International Studies and at the Institute for Political Economy.

In 1988, he served in the Reagan Administration as speech writer to Secretary of Agriculture Richard Lyng, and in 1989 he served in the administration of President George H. W. Bush, in the General Counsel's office at the U.S. Department of Energy.

Wolski then became an attorney with the Pacific Legal Foundation until 1997, where he was counsel of record at the petition stage in Suitum v. Tahoe Regional Planning Agency, 520 U.S. 725 (1997).

He was General Counsel and Chief Tax Adviser to the Joint Economic Committee of the U.S. Congress in 1999 and 2000.

On September 12, 2002, President George W. Bush nominated Wolski to a seat on the U.S. Court of Federal Claims.