India, Jan. 6 -- As Nicolas Maduro and his wife Cilia Flores pleaded not guilty in a Manhattan courtroom Monday, the proceedings were overseen by a familiar figure in high-stakes legal battles: 92-year-old U.S. District Judge Alvin Hellerstein. The jurist brings a decades-long career of handling complex, politically charged cases to the historic prosecution of the captured Venezuelan leader.

Appointed to the bench by President Bill Clinton in 1998, Hellerstein has served for over 25 years in the Southern District of New York, often called the "Mother Court." A Columbia Law School graduate and former U.S. Army lawyer, he is known for his judicial independence and meticulous handling of lengthy, intricate cases.

The Maduro case itself was...