[2] After law school, Easterbrook clerked for judge Levin Hicks Campbell of the U.S. Court of Appeals for the First Circuit from 1973 to 1974.

The Post concluded that good lawyers were no longer willing to work for the Solicitor General and attributed this to Bork's role in firing Archibald Cox as Watergate special prosecutor.

The three bottom-of-the-barrel selections were Robert Reich (later Secretary of Labor in the Clinton Administration), Danny Boggs (future Chief Judge of the Sixth Circuit), and me.

[2] The American Bar Association gave Easterbrook a low "qualified/not qualified" rating, presumably due to his youth and relative inexperience.

[5][6] Among Judge Easterbrook's most prominent opinions are: As a young judge in one of his early opinions, Kirchoff v. Flynn, 786 F.2d 320 (CA7 1986), a lawsuit over an arrest for feeding pigeons in a park, Easterbrook used such language as "trundled to the squadrol" to describe an arrest; and states of the pigeon-feeder that she "will never be confused with the 30th Earl of Mar, whose hobby was kicking pigeons".

University of Chicago Law School Dean Saul Levmore stated that "Easterbrook is an important influence on legal education through his judicial opinions.

In a section devoted to Easterbrook's judicial demeanor, the report claims he "has consistently displayed a temperament that is improper for a Circuit Judge.

The Council pointed to another opinion, Kale v. Obuchowski, which derided a lawyer's argument as "pettifoggery" and concluded that the appeal was "frivolous, doomed and sanctionable".

[citation needed] However, this review by the council was never repeated, lending partial support to the defenders of Easterbrook and Posner that the report was an opportunity for anonymous venting by lawyers who were unhappy with the results of Seventh Circuit decisions, in no small part thanks to the decisions of Reagan appointees Easterbrook and Posner.

[19] In June 2009, Easterbrook wrote the decision in NRA v. City of Chicago holding that the Second Amendment, which protects the right to keep and bear arms, did not bind state governments.

In December 2017, Easterbrook supported the 4–3 en banc decision to reverse an earlier federal magistrate judgment that a confession had been unlawfully coerced from 16-year-old Brendan Dassey.

Easterbrook in his concurrence called on the Supreme Court to hear the case, and also pointed out its parallels with June Medical Services v.

Easterbrook wrote, "The Board [of Immigration Appeals] seemed to think that we had issued an advisory opinion, and that faced with a conflict between our views and those of the Attorney General it should follow the latter.

Yet it should not be necessary to remind the Board, all of whose members are lawyers, that the 'judicial Power' under Article III of the Constitution is one to make conclusive decisions, not subject to disapproval or revision by another branch of government."

[24] On June 29, 2020, Easterbrook wrote the opinion to reinstate significant voting restrictions in Wisconsin, originally put into place when Republicans controlled all branches of state government early in the previous decade and which U.S. District Judge James Peterson had overturned on constitutional grounds in July 2016.

Easterbrook wrote that even though the voting restrictions are discriminatory, it was purely based upon party affiliation (the areas most impacted are heavily Democratic leaning).

[25][26] On August 2, 2021, Easterbrook wrote the unanimous majority opinion upholding Indiana University's requirement for students to get the COVID-19 vaccine.

[27] Ten days later, circuit justice Amy Coney Barrett left the decision in place, denying a motion to block the policy temporarily while the challengers sought review from the Supreme Court.

[28] A few months later in a similar case, the full Supreme Court likewise declined a request to block vaccine requirements for health care workers in Maine.