Lewin in 2017
Lewin is originally from Rochester, New York, but lived outside of Boston for several years as a young boy. As early as nursery school, he was an avid sports fan, and he got his start in broadcasting as the radio commentator for the Rochester Red Wings at the age of 16. After graduating from Northwestern University (where he was a member of the Lambda Chi Alpha fraternity) in 1990, Lewin became the Red Wings' regular play-by-play announcer.
Lewin went on to call Baltimore Orioles games on the radio in 1995 and 1996, on TV for the Chicago Cubs on WGN in 1997 and on TV for the Detroit Tigers from 1998-2001 on Fox Sports Detroit. In 2000, he was the first-ever recipient of the Ty Tyson Award for Excellence in Sports Broadcasting, awarded by the Detroit Sports Broadcasters Association. He was the TV voice for the Texas Rangers from 2002 through 2011, usually on Fox Sports Southwest but also on local broadcasts for KDFI, KDFW and TXA 21. The Rangers organization announced on October 11, 2011, that Lewin would not be returning as play-by-play announcer for the team. On February 9, 2012, it was announced that Lewin would be joining the New York Mets Radio Network, succeeding Wayne Hagin. He shared play-by-play duties with Howie Rose on Mets broadcasts. Lewin left his position with the Mets following the 2018 season. As of the 2019 MLB season, Lewin serves as a part-time play-by-play announcer for Boston Red Sox Radio Network broadcasts alongside Joe Castiglione.
Lewin was one of the original play-by-play commentators for Fox Major League Baseball, calling regular season regional games from 1996-2011. He started on the fourth regional crew calling games, but by 1999 was promoted to the number three booth where he would remain from 1999-2011. He would often fill in for principal play-by-play men Joe Buck (with Tim McCarver during the regular season) or Thom Brennaman (with Steve Lyons during the postseason). Lewin left Fox Sports after his contract with Fox Sports Southwest was not renewed. Since 2006 Fox prefers hiring national play-by-play announcers who work more than one sport..
During football seasons past, Lewin served as both a sideline reporter and play-by-play man for Fox NFL and called NFL games for SportsUSA/Jones Radio. From 2005 to 2016, he was the radio voice of the San Diego Chargers (he left after the team's move to Los Angeles at the end of the 2016 season). On August 26, 2006, Lewin provided television play-by-play for Fox Sports' Fox Saturday Baseball game of the week between the New York Yankees and Los Angeles Angels of Anaheim. That game took place at Angel Stadium of Anaheim. When the game was over, he traveled 90 miles down to Qualcomm Stadium in San Diego to provide radio play-by-play coverage of the San Diego Chargers' NFL preseason game against the Seattle Seahawks for the Chargers Radio Network. The two games announced in one day was similar to Ted Leitner's time as announcer for both the Chargers and the San Diego Padres when he would broadcast a Chargers game then travel to join the Padres broadcast late in the baseball season.
Lewin has also subbed in as the Dallas Stars play-by-play man when Dallas' usual lead voice, Ralph Strangis, was recovering from a car accident in 2003. He also did play-by-play for Fox NHL Saturday in 1998 and FSN Detroit's coverage of CCHA hockey.
On October 29, 2010, it was announced that Lewin would be moving to 105.3 The Fan to host a new show in their 11am-2pm time slot. The new show started on November 1, 2010, with Greg Williams and Richie Witt moving their show to the 2pm-7pm slot. On Monday, November 29, 2010, it was announced Mark "Elf" Elfenbein would be joining the show now named The Josh and Elf Show. Following Lewin's hiring by the New York Mets and departure from The Fan, Elf and friends was launched. Numerous personalities tried out to fill Lewin's spot. He would eventually be replaced by Jane Slater, making it The Elf and Slater Show.
Lewin is employed by the Big Ten Network calling football games. He also has called Conference USA football on Sports USA as well. On June 2, 2016, he was hired to be the play-by-play announcer for the UCLA Bruins football team.