Halpern attended Hackley School in Tarrytown, New York until 1963 and earned a B.S. at the Wharton School of the University of Pennsylvania in 1967. His J.D. came from the University of Pennsylvania Law School in 1972, followed by an LL.M. in Taxation from New York University Law School in 1975, earned while he worked as an associate in the law firm of Mudge, Rose, Guthrie and Alexander in New York City.
He taught law at Washington and Lee University and St. John's University, and New York University until 1979, then briefly returned to private practice with Roberts and Holland in New York City before joining the legal staff of the Internal Revenue Service from 1980-83.
Halpern was appointed by President George H. W. Bush as Judge, United States Tax Court, on July 3, 1990, for a term ending July 2, 2005, and re-appointed by George W. Bush on November 2, 2005, for a term ending November 1, 2020. He retired on October 16, 2015, but continues to perform judicial duties as Senior Judge on recall.
- Colonel, U.S. Army Reserve (retired).