After serving a 2 - 6-year prison sentence, the New York Supreme Court Appellate Division, Second Department, reversed Wills' convictions and ordered a new trial.

[10] Wills later cited this experience as his motivation to push Mayor Michael Bloomberg to expand rental subsidies stripped from the city budget in 2011.

[11] In August 2013, Councilman Wills secured 4.4 million from 15.5 billion of NYC's capital budget and spent every dollar toward Education initiatives, making him the largest benefactor of schools in the borough.

[12] In 2016, Councilman Wills also started a, first of its kind, New York City Council fund (13 million) that purchased distressed mortgages from local communities and renegotiated favorable  loan terms which allowed foreclosed residents to stay in their homes in efforts to prevent homelessness.

In November 2011, he pleaded guilty to misdemeanor criminal mischief, admitting to stealing items and damaging property in an incident that he called a business dispute.

The conviction resulted in no jail time or probation, but Wills had to pay restitution totaling $3,000 and perform 3 days of community service.

[18][19] On February 2, 2015, he was arrested again and charged with five felony counts of failing to disclose financial dealings on five separate disclosure reports filed with the city's Conflicts of Interest Board between 2012 and 2014.

[21] Wills argued that the vast majority of his charges stemmed from the office of New York State Attorney General Eric Schneiderman, who is an opponent of the Southeast Queens Democratic community and largely endorsed his primary opponent, future-Congresswoman Kathleen Rice, in the 2010 Democratic primary for New York State Attorney General.