During 2019 Chicago mayoral election, Green ran for the office as a candidate, but withdrew on January 1, 2019 citing insufficient campaign resources to fight a challenge by Willie Wilson to signatures on his ballot petition.

Records show that at least five other businesses Green has started (Urban Eyes Development, O and G Family Enterprises, Chicago Sweet Dreams, Majostee Realty, and Sunbend LLC) have similarly undergone involuntary dissolution.

In June 2020, Green started protesting along with other activists against Chase Bank's loan policy and demanded to retain and implement Community Reinvestment Act.

[11] On June 3, 2020, WBEZ published a report in which it was written that, in over a six year period, Chase Bank only handed out 1.9 percent of total loans to black-majority neighborhoods.

[16][17] In June 2022 Green announced that he intended to run for mayor of Chicago again on a platform focused on public safety, modernizing city government, economic development, and climate change.

The Sun-Times reported Green also accepted Paycheck Protection Program funds himself of $20,833, the maximum available to a sole proprietor.