Bleich was admitted to study at Harvard University but deferred for a year to take a public policy fellowship at the Coro Foundation in St. Louis, Missouri, where he became involved in juvenile justice issues.

He was legal assistant to Judge Howard M. Holtzmann of the Iran-United States Claims Tribunal at The Hague from 1991 to 1992, and Special Rapporteur to the Permanent Court of Arbitration.

[5] Bleich joined the Los Angeles-headquartered firm Munger, Tolles & Olson LLP in 1992, and was made partner three years later, in December 1995.

He moderated a discussion on human rights in the new administration at the 2009 American Bar Association's Section of International Law Spring Meeting in April 2009.

[9][10] Bleich's practice focused on cybersecurity,[11][citation needed] trade,[12] and international disputes, as well as on-pro bono work.,[13][14] He was selected in 2014, 2015, and 2016 as one of the leading 500 Lawyers in the U.S.[15][16] Serving pro bono, he obtained posthumous admission to the California Bar for a Chinese national, Hong Yen Chang, in a petition addressing the unlawful exclusion of Chinese in the 1890s, leading the Court to "right this historic wrong.

"[17] Bleich also successfully represented a victim of domestic violence in an action against her abuser in a second unanimous decision by the California Supreme Court.

[21] Bleich joined Cruise LLC, the autonomous vehicle company backed by GM, Honda, Softbank, Microsoft, Walmart, and T. Rowe Price as Chief Legal Officer in 2020.

[25] In 2018, Flinders University in Adelaide, South Australia, named Bleich a professorial fellow to its College of Business, Government and Law.

[28] Other key achievements included overseeing record growth in trade between the U.S. and Australia, bringing the Defense Trade Cooperation Treaty into force, establishing new alliance agreements for satellites and cyber, executing a new space cooperation agreement that supported the Mars Curiosity rover landing, leading joint U.S.-Australia efforts in Afghanistan's Oruzgan province, and promoting regional efforts to reduce domestic violence.

"[30] During the Clinton administration, Bleich served as director of the White House Council on Youth Violence, formed during the aftermath of the Columbine High School massacre.

[34] Bleich participated in PG&E's reparations to all wildfire victims, the company's acknowledgement of criminal wrong-doing, and its successful emergence from Bankruptcy.

[38] Bleich served on the Fulbright Foreign Scholarship Board after being appointed by President Obama in November 2014, and was later elected vice-chair and then chair for three successive terms.

[39][40] Bleich served by appointment of former secretary of state John Kerry on the board of the East West Center as a member of the executive committee from 2017 to 2021.

Bleich was appointed by Chief Justice Tani Cantil-Sakauye to serve as Vice-Chair of the Rules Revision Commission for the State Bar.

[42] Bleich has served on a number of other private company and non-profit boards since 2014, including RAND Australia,[43] the Pratt Family Advisory Board,[44] Futures Without Violence,[45] the World Affairs Council,[46] the American Security Project,[47] Verified Voting,[48] the San Francisco Symphony, the Folger Shakespeare Library,[49] and the Sorensen Center for International Peace and Justice.

[6] Bleich has also been recognized for his pro bono service to immigrants, homeless and foster youth, veterans, victims of gun violence, survivors of domestic abuse, human rights organizations, religious and racial minorities, gay and lesbian service members, journalists, native Americans, detainees, and others victims of discrimination.

[55] In November 2017 he received the Ruth Bader Ginsburg Award for Excellence in the Legal Profession[56] from the Jewish Bar Association of San Francisco.