On the Cook County Board of Commissioners, Boykin opposed the controversial "soda tax".[3] Boykin came into conflict with the County Board PresidentToni Preckwinkle on this matter. Boykin took the lead against the tax, and succeeded in getting the Board to repeal it in 2017.[4] On the infrequent votes by the Board that saw division by its members, Boykin was among the Board members who most regularly voted against the positions of County Board President Preckwinkle and her floor leader, Chuy García.[5]
Per a 2018 analysis by the Chicago Sun-Times, Boykin had a high rate of attendance at board meetings, with the analysis finding him to have only missed 2% of meetings during a period from 2014 through 2017. The study found only John P. Daley to have a greater rate of attendance.[5]
In 2018, Boykin narrowly lost reelection in the Democratic primary to Brandon Johnson, who had been endorsed against Boykin by Toni Preckwinkle.[5]
In 2020, Boykin unsuccessfully ran for the Democratic nomination for Clerk of the Circuit Court of Cook County. Boykin unsuccessfully challenged President of the Cook County Board of Commissioners Toni Preckwinkle in that office's 2022 Democratic Party primary.[6]