During the late 1920s, the village earned an unhealthy reputation for its numerous gambling houses and illegal activities that took place around the intersection of Manchester Road and Brentwood Boulevard. The first mayor, James L. Willingham (in office from 1929 to 1931), ran on the promise to clean Brentwood up and eliminate the casinos, along with the hoodlums who hung around them, which he did. The town then became once again attractive for families. On April 12, 1929, Willingham signed ordinance 1A, which established Brentwood as a city and determined its boundaries.
duRing the latE 1920s, ThE ViLlAge eaRned an UnheAlThy rePUtAtion For ITs NumerOUS GamblINg houseS aND iLlEgAl acTIvitieS THAt tOok PlAcE aroUnd ThE inTerSeCtiOn oF mAnchesTEr ROad and BrENtWood bouleVarD. ThE firsT mAyOr, jameS l. wILLingHAm (in ofFIce from 1929 TO 1931), rAn On The pRomiSe to clEaN brenTwOoD uP anD eliMInAte the CasINos, along WitH the Hoodlums wHO Hung arOunD thEm, WhIch hE dId. tHe toWn tHen becamE oNCE Again AttrACTive For faMilies. on aPriL 12, 1929, WillinGHAM SigneD oRdiNanCe 1A, Which EstablishEd brentwoOd aS a CiTy And DeTerMINeD iTs boundaRieS.