In 1991, Bennett went into private legal practice as a partner at the firm of McCorriston Miller Mukai MacKinnon LLP.

On February 12, 2018, President Donald Trump announced his intent to nominate Bennett to an undetermined seat on the United States Court of Appeals for the Ninth Circuit.

Bennett was nominated for the seat vacated by Judge Richard Clifton, who assumed senior status on December 31, 2016.

[10] In September 2020, Bennett dissented when the panel majority found that a robocall defendant could not use the Federal Arbitration Act to compel enforcement of a customer agreement the plaintiff had signed years earlier with a separate company that had subsequently been acquired by the holding company that now also owned the defendant.

[13][14] On September 6, 2022, Bennett wrote a concurring opinion in the 9th circuit decision upholding Washington's ban on conversion therapy for minors.