June 2020 Primary Election

In February 2020, Pinto announced her candidacy for Ward 2 Councilmember after incumbent Jack Evans resigned amidst an ethics scandal. Evans resigned before his colleagues could potentially expel him.^[9] As with other candidates, Pinto ran in the primary election for the Democratic nomination and the special election to fill the remainder of Evans' term.^[10]

Pinto was the last entrant into a crowded field that included Evans (who filed to run in both the primary and special elections just ten days after he resigned following multiple ethics violations).^[9] Pinto touted that she was the only candidate with business, tax, and legislative experience, which was needed in the wake of the COVID-19 pandemic.^[6] Karl Racine endorsed her campaign.^[3]

In early polls, Pinto trailed behind opponents with only two to three percent of the vote. However, after the Washington Post editorial board endorsed Pinto, claiming that she would provide a "needed new start," she began to gain momentum.^[11]

Pinto garnered support from Congressmen Richard Blumenthal, for whom she had previously worked,^[12] and Joe Kennedy III, who previously received $7,500 and $12,800 in donations, respectively, from her father James Pinto.^[3][13]

Pinto pulled off a surprise victory, earning 28 percent of the vote in a field of eight candidates listed on the ballot and ultimately winning the Democratic primary by about 300 votes.^[14][8]

Following her June 2020 primary election victory, Washington City Paper reported that Pinto had never previously voted in a DC election. Among Ward 2 candidates, she had the lowest share of D.C. contributors and the most money from out-of-state donors. Pinto was the only candidate who did not participate in D.C.'s Fair Elections public financing program, which allowed her to self-fund $45,000 for her campaign.^[3][15]

June 2020 Special Election

In the June 16 special election to finish the remaining term on the vacant Ward 2 Council seat, Pinto won with 43 percent of the vote in a field of seven candidates.^[16][17][2]

November 2020 General Election

Pinto faced multiple challengers in the general election, focusing their campaigns on her finances and local expertise. Opponents included Peter Bolton, the D.C. Statehood Green Party candidate, and independents Martín Miguel Fernández and Randy Downs.^{[18][19][14][20][21]}

In 2021, Pinto was accused of breaking campaign finance laws in an effort to retire her campaign debts. At a $500-a-head fundraiser hosted by a Ward 2 developer, Pinto raised $21,000. That violated a DC law prohibiting candidates to pay off campaign debts by fundraising more than six months after being elected. Pinto said that, in meetings with the Office of Campaign Finance (OCF), she specifically asked if such a fundraiser would be permittable and that OCF officials did not raise any objections. OCF disputed this characterization.^[22]