Berkowitz was born on February 4, 1962 in San Francisco, California. He received his degrees from Harvard College (1983, government and economics, with honors), Cambridge University (MPhil, polar studies, 1986), and The University of California Hastings College of Law (1990). He moved to Alaska in 1990 and is a lawyer and business owner.
Further information: 24th Alaska State Legislature
Berkowitz was the Democratic Minority Leader in the Alaska House of Representatives from 1999 to 2007. He was first elected to represent District 26 (Anchorage) in 1996, and then re-elected in 1998, 2000, 2002, and 2004.
In the 2006 election, Berkowitz was the Democratic nominee for Lieutenant Governor of Alaska, running with gubernatorial nominee Tony Knowles. Knowles and Berkowitz were defeated in the general election by Sarah Palin and Sean Parnell, losing by 48% to 41%.
In 2008, Berkowitz ran for election as U.S. Representative for Alaska's At-large congressional district, held by scandal-plagued Republican Don Young, who was seeking his nineteenth term in Congress. Berkowitz defeated Diane Benson in the August 26 Democratic primary by a substantial margin.
The initial results from the general election on November 4, 2008, showed Young leading the race, but with many absentee and provisional ballots left to be counted, the race was not called. On November 12, 2008, the media declared that Young, 75, had retained his seat in the United States House of Representatives, for his 19th term. Young received 50% of the vote compared to Berkowitz's 45%.
Berkowitz himself conceded defeat on November 18, 2008, after counting of absentee and provisional ballots had mostly been completed and Young had a clearly insurmountable lead. Berkowitz received more votes in 2008 (142,560) than any Democrat who had ever run against Young for Congress, and the 2008 race was the closest any Democrat had come to unseating Young since 1990, when John Devens of Valdez received 48% of the vote.
Berkowitz indicated he was interested in challenging incumbent Governor Sarah Palin before her surprise resignation in 2009. Berkowitz entered the race despite Palin's resignation and on August 24, 2010 he defeated State Senator, Hollis S. French to win the Democratic nomination. He and running mate for Lieutenant Governor Diane E. Benson faced incumbent Republican Governor Sean Parnell in the November general election and were defeated by a margin of 59% to 38%.
Berkowitz ran for mayor of Anchorage in 2015. He finished ahead of the rest of the field in the nonpartisan primary on April 7, advancing to a runoff with Assemblywoman Amy Demboski. He was endorsed by third-place finisher, former Republican state representative Andrew Halcro. He won the runoff election on May 5 by a 19-point margin.
Comments Berkowitz had made on the Bernadette and Berkowitz Show attracted controversy. In the context of a debate on Oct. 13, 2014, with co-host Bernadette Wilson over same-sex marriage, Berkowitz had said, "I support the idea of adults being able to choose who they have a relationship with. Father and son should be allowed to marry, if they’re both consenting adults — if you’re defining marriage as the bundle of rights and privileges that’s now accrued to people, then yes." Berkowitz later called the remark a "hypothetical insinuation", denying that he supports incest.
On July 1, 2015, Berkowitz was sworn in as Anchorage's mayor. In his inauguration speech, he urged city residents and leaders to work to overcome differences and "rise above the immediacy and smallness of the moment".
Berkowitz took the position of Senior Vice President of the Anchorage, Alaska branch of Strategies 360 in February, 2011.
Berkowitz and Bernadette Wilson were co-hosts of the Bernadette and Berkowitz Show on Anchorage radio station KFQD in 2014. He left the show when he began his mayoral run.