When the Rev. Michael Pfleger marched against violence, he marched against people like Phillip Dupree.



Dupree, 25, was a gang member with a record of arrests for drugs and guns. But last summer, Dupree showed up at Pfleger's door asking for help.



"He was just tired of the streets, he looked for help and support to make that change," Pfleger said. "I watched him go from people we called out during the marches to walking the marches with us."



Around 2:50 p.m. Wednesday, Dupree was riding with his 62-year-old grandmother in the 8000 block of South Ashland Avenue in the Gresham neighborhood when someone shot into their small Kia, according to police.



Dupree died on the scene, according to the Cook County medical examiner's office. His grandmother was taken in serious to critical condition to Advocate Christ Medical Center in Oak Lawn, said Officer Thomas Sweeney, a police spokesman.



The Kia, pocked with bullet holes, came to rest near a hair braiding business in the 7900 block of South Laflin Street -- about five blocks down the street from Pfleger's church, St. Sabina.



Dupree was among three people killed and at least seven wounded in Chicago on Wednesday into Thursday. Fourteen days into the new year, nearly 150 people have been shot in Chicago so far, 23 of them fatally.



Dupree had racked up more than two dozen mostly misdemeanor cases involving marijuana possession, criminal trespassing and gang loitering. But toward the end of the last year, he was charged with aggravated unlawful use of a weapon and aggravated fleeing, both felonies.



It was around this time that Dupree started going to St. Sabina and appeared to be committed to changing his life, Pfleger said.



"There is not a whole lot of support out here for people who want to make a change," the pastor said.



Just last week, Pfleger said he saw Dupree walking on the street and briefly chatted with him about how he was doing. Pfelger remembers telling him to have faith and stay focused.



"Unfortunately, the streets aren't so forgiving of change," Pfleger said.



In other shootings:



• A 25-year-old man was killed and his 23-year-old girlfriend was wounded as they drove down the Chicago Skyway around 1:30 p.m. when someone opened fire from a black SUV, police said.



Elliott Brown, of the 4000 block of South Calumet Avenue, was pronounced dead on the scene. The woman was wounded in the arm, officials said.



• Shortly before 9:30 a.m., an 18-year-old man was found shot in the head shortly in the first block of South Kenton Avenue in the West Garfield Park neighborhood, according to Officer Janel Sedevic, a Chicago police spokeswoman.



Preliminary information indicated the man suffered a wound to the head and was taken in critical condition to Stroger Hospital, Sedevic said. Later Wednesday afternoon, police said the man had suffered wounds to the chest and legs, and was pronounced dead at the hospital.