He was the legal architect and defender of Mexico's drug war, which has left tens of thousands of dead or missing but has made no major dent in drug trafficking.
He headed an office that had direct contact with US authorities during the catastrophic gun-smuggling program known as "Operation Fast & Furious," which funneled guns south across the border and fueled the violence.
And on his watch, federal investigators slapped fabricated charges of kidnapping on indigenous women after a confrontation between street vendors and federal police in central Mexico, leading to years of unlawful jail-time.
Eduardo Medina Mora, the name tacked to such a stained record, has nonetheless been handed a seat on Mexico's Supreme Court.
Mexico's Senate approved Medina Mora as a Supreme Court justice earlier this week, despite a late push on social-media led by prominent leftist figures to block his nomination.
Somehow, it wasn't so surprising.
Across three presidential administrations and atop some of the most important jobs in the country, Medina Mora has managed to oversee some of the worst governmental blunders in Mexico in recent years — yet he keeps getting promotions in the ranks of power.
His most recent job was ambassador to the United States, which Medina Mora held since January 2013 and quit on Tuesday in anticipation of President Enrique Peña Nieto's submission of his name for approval as a new justice.
Peña Nieto's officialist Institutional Revolutionary Party, or PRI, and the center-right National Action Party, known as PAN, combined votes against opposition from leftist lawmakers to approve the nomination.
More than 20 Mexican human-rights and civil organizations had previously denounced the appointment, calling Medina Mora responsible for violations committed by security forces during protest movements in 2006 in San Salvador Atenco and in Oaxaca. He was secretary of public security at the time under President Vicente Fox.
Medina Mora also faced rebuke for his attempt to challenge the decriminalization of abortion in Mexico City at the federal level in 2007, and for failed security operations he oversaw in Ciudad Juarez and in the state of Michoacan, during his time as attorney general in the administration of President Felipe Calderon.
The list goes on, opponents said.
"When there is deficiency, corruption, or failures in the justice system, these fallacies should be brought before the Supreme Court," said Edgar Cortez, an investigator with the Mexican Institute for Human Rights and Democracy, in an interview Wednesday. "Now [with Medina Mora's appointment], it seems less realistic that the tribunal will play this role and that human rights will be upheld in this country."
Mexico's government has been grasping for legitimacy after protests and worldwide condemnation over the case of the 43 teachers college students disappeared in the state of Guerrero last September. The disappearances came amid international pressure from the United Nations and other organizations over the widespread use of torture and extrajudicial killings by Mexican authorities.
Making matters worse, President Peña Nieto, his wife, and his finance secretary came under fire when allegations surfaced of cozy real estate deals with companies linked to government contractors.
The appointment of a politically damaged figure like Eduardo Medina Mora to Mexico's Supreme Court doesn't appear to be helping the government's image problem.
Above, the confirmation hearing in Mexico's Senate for Eduardo Medina Mora's appointment to the Supreme Court.
Perhaps the most serious governmental failure linked to Medina Mora is Operation Fast & Furious, which occurred during the Calderon government.
In this period, a US weapons-smuggling sting allowed more than 2,000 firearms to "walk" into Mexico illegally, in a failed attempt to track them to top cartel leaders.
Some of the weapons were later linked to high-profile homicides in the resulting drug violence, such as the killing of US Border Patrol Agent Bryan Terry in December 2010 by an AK-47 that entered Mexico under "Fast & Furious."
Other such guns were used in the tragic Villas de Salvárcar massacre in Ciudad Juarez in January 2010, in which 17 mostly student and aspiring athletes were killed by an armed commando during a house party.
A US Justice Department report published in September 2012 showed that American officials managing "Fast & Furious" inside Mexico had contact with Medina Mora's office during the program. An investigative report by Univision Noticias noted that US officials briefed Medina Mora on the program in 2007.
But Medina Mora pushed back in recent days against allegations that he approved "Fast & Furious" during his time as attorney general.
"I would have never authorized this kind of operation [...] a grave criminal practice such as weapons trafficking that has cost the lives of thousands of people in our country and the whole world," Medina Mora wrote in a letter addressed to mexican journalist Carmen Aristegui, who reported last week that he knew about "Fast & Furious."
'To try and attribute to me, part or all of this decomposition that you refer to is biased, speculative, and unscrupulous.'
Other dark moments and embarrassments mark Medina Mora's record.
In 2009, federal agents under Medina Mora swooped into Michoacan state for a highly touted anti-corruption operation. Dubbed the Michoacanazo, dozens of state and municipal government officials in Michoacan were detained for alleged links to organized crime groups.
A year and a half later, all of the detainees walked, due to lack of proof.
In August 2006, three indigenous Otomí women, Alberta Alcantara, Teresa Gonzalez and Jacinta Francisco, were accused of kidnapping federal agents after a melee with street vendors in the state of Querétaro. The women were apparently picked up randomly and spent more than three years behind bars.
They were eventually freed when Mexico's Supreme Court intervened in the face irrefutable evidence that the women were not involved in the case. Medina Mora had defended the government's actions.
In May 2006, when Medina Mora was public security secretary for President Fox, a massive federal police operation sought to repress a campesino protest in San Salvador Atenco, Mexico state, while Enrique Peña Nieto served as governor.
During the operation, two students were killed and 26 women who were detained said they were sexually tortured by authorities. The case is still being heard by the Inter-American Commission on Human Rights.
Later in the year, a popular uprising in the state of Oaxaca also ended in federal police repression.
During the conflict, 18 people were killed and hundreds more injured or detained. Human rights groups denounced the excessive use of force, arbitrary arrest, torture, and fabrication of charges against protesters in Oaxaca, allegations that were later heard and confirmed by the Supreme Court.
Mexican academic Alejandro Madrazo Lajous headed a Change.org petition signed by thousands against Medina Mora's confirmation.
"Our country is at the crossroads," Madrazo wrote. "In the middle of a severe legitimacy crisis in which an important part of the population believes that the authorities responsible for maintaining order and administrating justice are characterized by their incapacity and arbitrariness in carrying out their mandate."
Medina Mora responded to Madrazo, disputing the claim that he was responsible for the "decomposition of security and justice."
"To try and attribute to me, part or all of this decomposition that you refer to is biased, speculative, and unscrupulous," Medina Mora said.
Human rights abuses aside, Medina Mora has resided outside of Mexico since 2010, when he was appointed Mexican ambassador to the United Kingdom. The Mexican Constitution explicitly states that Supreme Court justices have to have lived in the country for the two years prior to their appointment, a requirement that Medina Mora doesn't fill.
VICE News contacted the federal government to ask why an exception was being made in this case, and the unofficial response given was that the rule doesn't apply to diplomats.
Medina Mora, who is cousin of Citigroup co-director Manuel Medina Mora, has also worked in the corporate sector. As Mexico passes controversial legislation including the recent energy reform, officials' corporate ties are coming under closer scrutiny.
"Part of his biography is that he has been a litigating lawyer at the service of the corporate and business sector," Cortez told VICE News. "This is a delicate point because he will participate in these debates and discussions and most likely will put business interests at the forefront, instead of the interests of the general population."
Mexican Supreme Court justices, which total 11, serve for 15-year terms.
Follow Andalusia Knoll on Twitter @andalalucha.