Boulware received an Artium Baccalaureus degree, cum laude, in 1993 from Harvard College and studied toward a Doctor of Philosophy in Sociology from 1995 to 1998.

[6] On June 5, 2014, Senate Majority Leader Harry Reid filed for cloture on the nomination.

[9] In 2015, Boulware began hearing a high-profile anti-trust lawsuit against the Ultimate Fighting Championship filed by several of its former fighters.

Boulware ruled that Rudin received ineffective legal representation from her late defense attorney.

[13] On September 9, 2015, President Obama nominated Boulware to a position on the United States Sentencing Commission.