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His fifth book is more personal: In Hoffa's Shadow: A Stepfather, A Disappearance in Detroit, and My Search for the Truth, published in the fall of 2019. In this memoir, Goldsmith explores who killed labor leader Jimmy Hoffa. He reveals the perennial mystery's connections to both broader American historical and economic trends, and Goldsmith's own family. Goldsmith's stepfather was Charles "Chuckie" O'Brien, who had lived with Hoffa and his family as a child and young adult. He later followed Hoffa into the union, and they remained associated. In 2001, the FBI found Hoffa's DNA in a 1975 Mercury car that O'Brien had borrowed after it was owned by a mobster. He denied Hoffa was ever in the car and said he was not involved in his disappearance that year.

Goldsmith questions a key premise of Martin Scorsese's 2019 film The Irishman due to the information he gathered for his own book about unions in the U.S., his stepfather Chuckie O'Brien, who was an associate of Jimmy Hoffa, and Hoffa's mysterious disappearance.

"We conclude only that when the nation has been thrust into an armed conflict by a foreign attack on the United States and the president determines in his role as commander in chief ... that it is essential for defense against a further foreign attack to use the [wiretapping] capabilities of the [National Security Agency] within the United States, he has inherent constitutional authority" to order warrantless wiretapping—"an authority that Congress cannot curtail.”

The Special Program, a screenplay exploring Goldsmith's experiences in the Department of Justice's Office of Legal Counsel, was sold to The Weinstein Company on December 16, 2013. According to the Spec Scout database, as of November 21, 2014, this project was "no longer set up with the Weinstein Company."

This book argues that the presidency after the 9/11 attacks was much more constrained and accountable than conventional wisdom suggests. Goldsmith asserts that the president is constantly under scrutiny and checked inside and outside the executive branch by variously motivated actors–courts and Congress, but also lawyers, inspectors general, ethics watchdogs, journalists, and civil society–who generate information about what the executive branch is doing, who force it to explain its actions, and who are empowered to change these actions when the explanations fail to convince. Goldsmith labels these multiple forms of watching and checking the presidency a "presidential synopticon," and claims that this synopticon reined in the George W. Bush administration's early excesses in the "war on terrorism," creating a consensus on counterterrorism policies by 2008 that explained the Obama administration's then-surprising decision not to change the counterterrorism policies it inherited in material ways. Goldsmith concludes that the presidential synopticon's constraints on the presidency also paradoxically empowers the presidency by making its counterterrorism actions more legitimate. But it also produces "unhappy consequences, including the harmful disclosure of national security secrets, misjudgments by the watchers of the presidency, and burdensome legal scrutiny that slows executive action." Goldsmith discussed the book on the Daily Show with Jon Stewart on April 4, 2012.

In 2007, Goldsmith published The Terror Presidency, a memoir about his work in the Bush administration and his thoughts on the legal opinions that were promulgated by the Department of Justice in the war on terror. His discussion covers the definition of torture, the applicability of the Geneva Conventions to the war on terror and the Iraq War, the detention and trials of suspected terrorists at Guantanamo Bay and elsewhere, and wiretapping laws. He is largely sympathetic to the concerns of the Bush administration's terrorism policies, but believes they made a huge strategic mistake by acting unilaterally rather than seeking congressional consent soon after 9/11. He believed that fear of another attack drove the administration to its focus on the hard power of prerogative, rather than the soft power of persuasion. In the end, he believed the fear and concentration on hard power were counterproductive, both in the war on terror and in the extension of effective executive authority.

Goldsmith also appeared on the Bill Moyers show on September 7, 2007. Moyers asked about the notable incident of his being in the hospital room of Attorney General John Ashcroft after he had been suddenly taken ill the day before. That day Ashcroft had ruled that Bush's domestic intelligence program, Stellar Wind, was illegal. It included provisions for warrantless wiretaps. Gonzales and Andrew Card, White House Chief of Staff, had come to try to persuade Ashcroft to change his mind and withdraw his memo. Goldsmith was there to support Ashcroft. Goldsmith said that, as Gonzales and Card left the room, Mr. Ashcroft stuck out his tongue at them behind their backs. President Bush re-authorized the program over the formal objections of the Department of Justice.

In April and May 2004, the Abu Ghraib prisoner torture and abuse scandal broke. In June, the Bybee Torture Memo was leaked. Goldsmith considered it to be "tendentious, overly broad and legally flawed." He worked to have the memos changed. Including his challenges of White House staff on issues related to domestic surveillance and trials of terrorists, he was successful in moderating some of what he considered to be the previous "constitutional excesses" embraced by the White House.

In June 2004, Goldsmith withdrew as legally defective the Bybee Memo and the Torture Memos, and advised DOD not to rely on the March 2003 memo. At the same time, he submitted his resignation. Several years later he said this was to try to force the administration to accept his withdrawal of the memo. OLC legal opinions written in August 2002 related to the government's use of enhanced interrogation techniques, or torture, on individuals detained as enemy combatants. Newsweek later reported in 2007 that the CIA had regarded the Bybee memo as a "golden shield" against potential prosecution of officials involved in the program.

But, Goldsmith was unable to have his office complete what he intended as the replacement legal opinions before he resigned on June 30, 2004. He said later that he had felt he had lost the confidence of the administration. By December 2004, the replacement counsel at OLC had reaffirmed the previous legal opinions.

In March 2004, the OLC concluded the e-mail program was not legal. Acting Attorney General James Comey refused to reauthorize it. On May 6, 2004, Goldsmith wrote in a 108-page memo:

Goldsmith said he resigned in 2004 largely because he felt he had lost the confidence of administration leaders. He notes that the White House Counsel Alberto Gonzales asked him to remain, while Addington, an influential White House figure, asked which other OLC opinions he intended to overturn. Goldsmith wrote in his book, "Nobody had said no to them before."

In addition, on March 14, 2003, after Goldsmith had been hired to work as a legal adviser to the General Counsel of the Department of Defense, John Yoo wrote a legal opinion at the request of the DOD General Counsel, five days before the US invasion of Iraq, concluding that federal laws did not prohibit torture by interrogators of foreign subjects overseas. (This memo was not revealed until 2008.)

In October 2003, Goldsmith was appointed to head the Office of Legal Counsel, which provides legal guidance to the president and all executive branch agencies, including those tasked with the interrogation of enemy combatants. This gave him the base for influencing debates within the Bush administration regarding the conduct of the War on Terror.

In 2002, Goldsmith joined the Bush administration as the Special Counsel to General Counsel of the Department of Defense, at a time when the government was developing plans for responding to the 9/11 attacks. In April 2003 he was nominated to be a United States Assistant Attorney General, tasked with leading the prestigious Office of Legal Counsel in the Department of Justice. The Senate confirmed him in October 2003. He resigned in July 2004 to join Harvard Law School. He wrote a book about his experiences there called The Terror Presidency (2007).

In August 2002, before Goldsmith joined the Bush administration, the Office of Legal Counsel, Department of Justice, had issued three documents, which became known as the Torture Memos, or the Bybee memo (referring to one in particular.) The Bybee memo was directed to the Acting General Counsel of the Central Intelligence Agency in relation to interrogation of a detainee, Abu Zubaydah. It authorized certain methods of torture (characterized by the Bush Administration as "enhanced interrogation techniques") for use with detained enemy combatants at the Guantanamo Bay detention center and other locations.

By September 2002, Jack Goldsmith had been hired to work as a legal adviser to the General Counsel of the Department of Defense, William J. Haynes II.

He worked at the Washington, D.C. law firm Covington & Burling from 1994-1996. He served as a professor at the University of Virginia Law School before going to the University of Chicago.

Goldsmith grew up the stepson of Charles "Chuckie" O'Brien, widely believed to have played a role in the disappearance of Jimmy Hoffa, former president of the International Brotherhood of Teamsters. Goldsmith attended and graduated from Pine Crest School in 1980. He matriculated and graduated from Washington & Lee University with a Bachelor of Arts summa cum laude in 1984. He earned a second B.A. with first class honours from the University of Oxford in 1986, a J.D. from Yale Law School in 1989, an M.A. from Oxford in 1991, and a diploma from The Hague Academy of International Law in 1992. He clerked for Judge J. Harvie Wilkinson III on the United States Court of Appeals for the Fourth Circuit from 1989 to 1990, and for Justice Anthony Kennedy of the Supreme Court of the United States from 1990 to 1991.

Jack Landman Goldsmith (born September 26, 1962) is an American lawyer and Harvard Law School professor who has written extensively in the fields of international law, civil procedure, federal courts, conflict of laws, and national security law. He has been "widely considered one of the brightest stars in the conservative legal firmament."