During his time at the Department of Justice, he received a Certificate of Appreciation from President Gerald Ford for his service in the resettlement of Indochinese refugees.

[2] In the first three years, Wolf's unit achieved more than 40 consecutive convictions, which included corrupt officials close to Boston Mayor Kevin White.

When Wolf announced he would become a Senior Judge in 2013, the Boston Globe published a summary of the most notable cases of his judicial career.

In a related case, The Supreme Court of the United States unanimously agreed with Wolf's decision in a landmark judgement on free speech, specifically the right of groups to determine what message their activities convey to the public.

[7] Judge Wolf's judicial work exposed corruption in the Federal Bureau of Investigation's handling of matters involving notorious criminals James “Whitey” Bulger and Stephen Flemmi.

In sentencing Sampson to life in prison, Wolf said:  "You personify the wisdom of [the poet Auden who wrote] “Evil is unspectacular and always human … And shares our bed and eats at our own table.”" He later added that "By committing horrific crimes that virtually compelled decent people in this community to condemn you to die, you have diminished, if not degraded, us all.

In 2006, The Boston Globe had opposed Kosilek's surgery because "private insurers rarely pay for sex-change operations" and "hormone treatment and expert therapy" are "sufficient".

However, in 2012, The Boston Globe wrote that Wolf's decision made a persuasive case that the surgery was "medically necessary, not an elective procedure," however "distasteful.

"[15][16] In his ruling, Wolf found that "Michelle Kosilek, who lives as a woman in a male prison facility, had experienced "intense mental anguish," and said there was a serious medical need" for her to have the procedure.

[21] In 2016, Judge Wolf, Justice Richard Goldstone, and colleagues formed Integrity Initiatives International (III) to combat grand corruption, also known as "kleptocracy."

"[23] In order to achieve this, III advocates for the creation of an International Anti-Corruption Court (IACC), a concept which Wolf first proposed in articles for the Brookings Institution and The Washington Post in 2014.

[24][25] The IACC proposal was further developed in a paper Wolf published in 2018 in Daedalus, the journal of the American Academy of Arts and Sciences, titled “The World Needs an International Anti-Corruption Court.”[26] In 2022, the American Academy of Arts and Sciences published a paper by Wolf, Goldstone and Professor Robert Rotberg, titled “The Progressing Proposal for An International Anti-Corruption Court.”[27] In 2016, President Juan Manuel Santos declared Colombia the first country to endorse the IACC.

[29] In May 2022, nearly 300 world leaders, including more than 30 Nobel laureates, more than 40 former presidents and prime ministers, from over 80 countries, signed a Declaration in support of establishing the IACC.

Prosecution in the IACC would, in many cases, result in the incarceration of convicted kleptocrats and thus create the opportunity for the democratic process to replace them with honest leaders.