Ross Ulbricht asked last week U.S. District Judge Katherine Forrest to spare him life in prison, admitting the Silk Road website was a “naive and costly idea” that destroyed his future.

The 31-year-old Ulbricht expressed his regrets in a letter to Forrest, who is scheduled to sentence him May 29. Ulbricht faces a mandatory minimum of 20 years in prison and a maximum of life.

“Silk Road was supposed to be about giving people the freedom to make their own choices, to pursue their own happiness, however they individually saw fit,” Ulbricht wrote to Forrest. “What it turned into was, in part, a convenient way for people to satisfy their drug addictions.”

“In creating Silk Road, I ruined my life and destroyed my future,” Ulbricht told Forrest. “I could have done so much more with my life. I see that now, but it is too late.”

Ulbricht, in U.S. custody since October 2013, asked Forrest to give him a sentence that will leave him “a light at the end of the tunnel.”

“Even now I understand what a terrible mistake I made,” he said. “I’ve had my youth, and I know you must take away my middle years, but please leave me my old age.”

Who is the judge deciding the fate of Ross Ulbricht?

That would be U.S. District Judge Katherine Forrest, born in New York. She received a B.A. with honors from Wesleyan University in 1986, and a J.D. from New York University School of Law in 1990. Katherine then joined Cravath LLP in 1990, becoming a partner in 1998.

Forrest’s main focus in her career as a lawyer was antitrust, intellectual property, securities litigation, contract, and general entertainment issues.

Forrest represented numerous companies in their pursuit of regulatory clearance from the FTC and DOJ, including the AOL/Time Warner merger, the sale of the Warner Music Group, the sale of WEA manufacturing, and the acquisition of Grey Goose by Bacardi.

Forrest was listed as one of the country’s leading practitioners for antitrust and intellectual property issues in Chambers USA 2007: America’s Leading Lawyers for Business.

She was also named in The International Who’s Who of Competition Lawyers, and listed in Who’s Who in America, Who’s Who of American Women and Who’s Who in the East. She was once named by The American Lawyer as one of America’s top 50 young litigators.

Katherine was a frequent lecturer before her tenure on the bench, addressing many legal and arts-related organizations, such as the Association of the Bar of the City of New York, the New York State Bar Association, the National Council on the Arts, and was invited to speak on “monopolization” for the Practicing Law Institute’s 46th Annual Antitrust Law Institute in 2005.

Forrest has authored several articles, including “Clearance of Cross-Border Transactions: Achieving Consistent US/EU Clearance Results” in the M&A Lawyer (June 2006), and “The State of E.U./U.S. Merger Coordination” in the International Mergers and Acquisitions Review (2006/07).

According to public records, Judge Forrest had $4.3 million at the time of her bench appointment. Some posit she is much richer.

National Defense Authorization Act

During her tenure as a judge, Forrest blocked enforcement of a provision in the National Defense Authorization Act that authorizes indefinite military detention for those deemed to have “substantially supported” Al Qaeda, the Taliban, or “associated forces.

On May 16, 2012, in Hedges v. Obama, Forrest ruled in favor of journalist Chris Hedges, activists, and journalists who feared they could be detained under a section of the NDAA.

“In the face of what could be indeterminate military detention, due process requires more,” Forrest said.

She noted it was in the public interest to reconsider so that “ordinary citizens are able to understand the scope of conduct that could subject them to indefinite military detention.”

“Can Hedges and others be detained for contacting al Qaeda or the Taliban as reporters?” Forrest asked the government at the hearing.

The government could not convince her they could not be detained.

“Failure to be able to make such a representation… requires the court to assume that, in fact, the government takes the position that a wide swath of expressive and associational conduct is in fact encompassed by 1021,” she wrote in her decision.

Journalist Chris Hedges called the ruling “courageous,” but that Forrest “did what she was supposed to do” considering “the law is so clearly unconstitutional,” he said.

Forrest’s ruling was later unanimously reversed by appellate court panel.

JP Morgan/Goldman Sachs

In August 2014, Forrest dismissed a price-fixing suit against Goldman Sachs, JP Morgan Chase, and Glencore, maintaining that, although the defendant’s actions did affect the aluminium marketplace, the plaintiffs failed to show the defendants had intended to manipulate prices.

“Plaintiffs pretty much today have to have smoking-gun evidence of a conspiracy or they cannot go ahead and try to prove that there was a conspiracy,” said Robert Lande, a University of Baltimore professor specializing in antitrust.

Silk Road

Forrest began presiding over the jury trial U.S.A. v. Ulbricht in January 2015, where Ross Ulbricht faced charges of having created and run the Silk Road online drug marketplace. He was found guilty on all counts and faces his sentencing this week.

In the proceedings, Forrest notably ruled that an emoji is permissible court evidence.

She shot down a retrial, despite the fact that two agents were later arrested due to their conduct during the investigation.

She sentences Ross Ulbricht May 29.