At the time of his nomination to serve as U.S. Attorney for the District of Massachusetts, Lelling had served for 12 years as senior litigation counsel for the U.S. Attorney's Office for the District of Massachusetts, prosecuting white collar crime, international drug trafficking, and other offenses. He is a member of the Federalist Society and a former member of the Boston Bar Journal's board of editors. During his tenure with the U.S. Attorney's Office in Massachusetts, Lelling led the prosecution of a billion-dollar pyramid scheme that defrauded almost 2 million investors. A former executive of Telexfree was sentenced to six years in federal prison for his involvement in the scheme. Lelling also helped prosecute Carlos Rafael, a fishing magnate known as "the Codfather" who pleaded guilty to mislabeling hundreds of thousands of pounds of fish, allowing him to illegally increase his profit margin via environmental fraud. He successfully prosecuted several golfing buddies for trading on inside information about American Superconductor.
In 2019, Lelling announced charges in the 2019 college admissions bribery scandal and is leading the prosecution. Lelling heads the securities and financial fraud unit that is prosecuting the case. The unit includes Assistant U.S. Attorneys Eric S. Rosen, Justin D. O’Connell, Leslie Wright, and Kristen A. Kearney.
In April 2019, Lelling indicted Massachusetts trial court judge Shelley M. Richmond Joseph and now-retired Court Officer Wesley MacGregor on obstruction of justice charges in regards to an April 2, 2018, incident where the judge and the court officer helped a twice-deported illegal alien who had again illegally entered the U.S. to evade arrest from the Newton District Court. Joseph and MacGregor face three different obstruction charges: conspiracy, aiding and abetting a fugitive, and obstruction of a federal proceeding. MacGregor has also been charged with perjury. Lelling said "We did not bring this case in response to the public debate over immigration enforcement. There are reasonable arguments on both sides of that debate, but this isn't a policy seminar, it's a law enforcement action."
Personal life
Lelling is married to Massachusetts juvenile court judge Dana Gershengorn and they have two children.
