Chris was sitting on a park bench in south Chicago when he started to recall his first real connection to the mob.  It was on May 7, 1922, the boss of the Castle family was killed in a drive-by shooting near his E. 116th Street a mere block from his home. Valenti was believed to have been personally responsible. Within hours the Castle underboss Silva Mangunna was fatally wounded in Lower Manhattan by Valenti and gunmen working for him. The next day, Valenti and some of his men attacked the new boss of the rival Castle family, they killed him too.  Joe the Boss Masseria wanted Valenti found and dealt with.  Masseria tapped Lucky and Lucky went to Frank.  Frank thought Vito should handle it however Meyers was there and thought Chris should handle it.  Meyers told Lucky that Chris was so good that he will gift wrap the man and have a bow on the casket.  

Lucky told them both that he needed a day or two to think on.  However, he didn’t have that luxury   Joe the Boss and his bodyguards were walking down Grand Street within a block of Police Headquarters.  Valenti men opened up on them, Joe and his men fired back.  The police filed out like army ants  and when the shooting was over, the gunmen had shot four men and two women, but had not harmed their targets just as Masseria and his men realized they didn’t hit their attackers.  Masseria tossed his pistol away along with his men.  Valenti got away by ducking down a close by alley and sliding into a restaurant.   The police covered the entire area but came up short.  Rumors have it that two police captains each received a payoff from each crime boss.  Chris got a call from Frank that Joe the Boss needed his help.

On May 13, 1922, Chris  walked out of his apartment at 80 2nd Avenue, and was rushed by three armed men who opened fire on him. Chris ducked into a store at 82 2nd Avenue with the gunmen in pursuit. They shot out the front window and shot up the inside of the store.  The gunmen fled across 2nd Avenue to a getaway car idling just around the corner on E. 5th Street.   Chris then gave chase with his pistols drawn firing at them as they ran.  Chris hit one in the back of the head and another in the chest with three shots as the gunmen turned to Chris.  The getaway driver took off in a mad rush.  The car was a Hudson Cruiser. The gunman jumped on the running boards as the car sped west on E. 5th Street towards the Bowery, guns blazing.  Chris was furious that he was shot at and could not get the men sent to kill him.   

Forty-eight hours later, on May 15, 1922 Umberto Valenti attended a meeting in a cafe at the corner of Second Avenue and E. 12th Street.  Accounts differ as to who was there. Masseria's key ally Giuseppe Morello is often said to have been present.  Apparently realizing his life was in danger, Valenti burst outside as the bullets began flying.  An eight-year-old girl standing nearby was wounded.  Valenti managed to make it on the running board of a passing taxi before collapsing mortally wounded.  The Herald stated, "Valenti, said to be strong in his hatred of Masseria, was killed coldly and with as little compunction as one would swat a fly." Gangland lore had long held that his killer was none other than Chris Lucchese. Just after this incident, Giuseppe Masseria began being referred to as "Joe the Boss”