Sass first ran for State Treasurer against incumbent RepublicanJack Voight in 1998; she lost with 754,177 votes to Voight's 814,380, with 31,452 for the Wisconsin Greens nominee, 28,561 for the Libertarian Tim Peterson, and 171 for the Taxpayers' Party candidate. She was a delegate to the 2000 Democratic National Convention; and ran unsuccessfully for the Wisconsin State Senate's 33rd District in a 2001 special election to succeed Margaret Farrow, losing the race to Ted Kanavas 10,238 to 3,557. She ran once more in 2002 against Voight, losing again with 720,445 votes to Voight's 824,049 and 114,955 for Green Paul Aschenbrenner; and ran unsuccessfully in 2004 for Milwaukee County Treasurer. In 2006, she defeated incumbent Voight on November 7, 2006, in a narrow upset victory by a margin of 8,648 votes with little party support. She had spent almost $4000 on the race, most of it coming from her own pocket. On November 2, 2010, Sass was defeated for reelection by Kurt W. Schuller. In February 2012, she lost to fellow Democrats Tim Carpenter and Spencer Coggs in the four-way non-partisan primary to win a place on the ballot for Milwaukee City Treasurer in the Spring 2012 election. Coggs polled 13,559 votes; Carpenter 12,880; Sass 5,089 and Socialist Rick Kissell 2,241. In August 2014 she lost to former Assemblyman David Cullen for the Democratic nomination for Milwaukee County Treasurer; Cullen drew 38,492 votes to Sass' 33,729. In 2018, she ran in the Democratic statewide primary for Wisconsin State Treasurer, this time facing two female opponents. One of her opponents was Cynthia Kaump, a small business owner and financial professional from Madison, Wisconsin, who also had been a political and investigative reporter on television news for over two decades. However, Kaumps’ momentum as she was gaining in the polls dropped significantly when a week before the primary it was revealed by the Milwaukee Journal Sentinel that she owed money to a tax preparer business. Sass’ main opponent in the primary was Eau Claire, Wisconsin native, Sarah Godlewski. Although a successful entrepreneur and lobbyist, Godlewski had an inside track as she was the National Finance Council Co-Chair for Ready for Hillary, the 2016 PAC for Hillary Clinton in her Presidential campaign and was the Wisconsin Women's Director for Clinton's 2016 Presidential bid. She also teamed up with Sass’ nemesis, Jack Voight to co-chair the Save Our Fiscal Watchdog Committee, a successful grassroots Get Out The Vote effort which defeated an April 2018 proposed amendment to the Wisconsin Constitution to remove the office of State Treasurer. Sass ran a spirited campaign stating if she won, “Sass says her goal as treasurer if she were to win this year would be to create a “State Bank of Wisconsin” to offer low-cost loans and services to citizens. Sass’ multiple campaigns gave her such an advantage that Godlewski & Kaump had to spend heavily on television ads to close the gap.. In the end Godlewski won the Wisconsin Democratic Party State Convention straw vote that was largely meaningless. However that and her television ad campaign allowed Godlewski to garner 41% to Sass’ 34% and 25% for Kaump. In 2020, Sass filed for Green CountySupervisor. She focused her campaign on corporate farms stating: “Green County has always been a farming community. These large farms are pushing farming families out that have been in our community for generations. We all need to help each other and fight for small family farms.” She faced attorney Skip Miller and in the April election was elected with 62% of the vote.
