Teddia “Teddy” Caldwell, 50, on Thursday, was sentenced to 14 years in prison, ending years worth of court proceedings for the head of the notorious Gary drug ring.
U.S. District Court Judge Philip Simon handed down the sentence, to run concurrently, after Caldwell admitted to leading a cocaine ring and aiding in the murder of Kevin Hood, a rival car wash owner and alleged drug dealer. Caldwell has testified in the trials of others involved with the murder, and Simon said he is “one of the most important and best cooperators” for the court.
“Had you not cooperated and been convicted, you would’ve been sentenced to life,” Simon told Caldwell.
Simon called the case “terrible all around,” and said that it wasn’t Caldwell’s first time in the system, referring to multiple armed robberies. He also said Caldwell had a limited work history and served in the military but was discharged for bad conduct.
Simon also said he is sympathetic to the fact that Caldwell’s mother was addicted to drugs and “somewhat abusive,” and that he has “serious medical issues.” Even though he ran a drug ring, Caldwell didn’t have many drug and alcohol issues, Simon said, which also helped the sentence.
“I hope that this sentence gives you hope for the future,” Simon said. “I’m only doing this because of your cooperation.”
During his sentencing, Caldwell began crying while apologizing to Hood’s family and his own family and friends. He also thanked the court for the opportunity to speak.
“I sit here a different man than I was when I walked in eight years ago,” Caldwell said. “I can honestly say that I’ve learned a lot and turned my life around.”
Several of Hood’s family members spoke during Caldwell’s sentencing, including his mother, Ellan Hood, and aunt, Mary Lee. His aunt said that his death remains difficult for the family, and they’re continuously reminded about how they never got to say goodbye.
“I saw him lying on the ground that day, and that still haunts me,” Lee said. “Kevin Hood, Jr. will never be forgotten because he’s given us so much to remember.”
Ellan Hood told the court that no one else’s family should go through what they’ve gone through, and no one’s child deserves to die like her son did.
“This is bittersweet,” she said. “I’m glad this horrendous case is over, but Kevin is still not coming home.”
Caldwell pled guilty in August 2022, according to Post-Tribune archives. Caldwell admitted to leading a cocaine ring from 2016 to 2018, according to court documents, which sold drugs out of his home and car wash business, Da Wash, located at Broadway and E. 20th Place.
Caldwell admitted to conspiring with Taquan “Boonie” Clarke, Devontae Martin and an unnamed person to rob Hood. The four men took a “large amount” of “cocaine and/or money,” and split the proceeds, according to Caldwell’s plea agreement.
Hood, 43, of Gary, was killed on July 28, 2017, during the robbery outside his business, Shine on Hand Car Wash, located near 15th and Massachusetts streets, according to the Gary Police Department. Martin drove through the car wash with an AK-47-style rifle to rob Hood of money and cocaine, according to the superseding indictment.
Martin jumped out of the vehicle, and the two got into a physical fight, during which his gun was discharged, according to court records.
Caldwell saw Martin and Hood fighting in the street, and Clarke ran up and shot Hood, according to court records.
Authorities linked another murder to Caldwell’s organization, but he only pleaded guilty in connection to Hood’s death.
In May, Devonte Hodge, 30, of Gary, received a life sentence at federal court for his involvement in the October 2016 murder of Akeem Oliver, 29. Both were involved with Caldwell’s drug ring, and Oliver was giving police information about Isaiah “Drizzy” Edwards’ June 2016 murder.
Assistant U.S. Attorney David Nozick called Hodge a “committed witness killer” at his hearing, and he estimated that Hodge could be responsible for as many as five to seven murders, according to Post-Tribune archives.
Caldwell is the estranged husband of Gary Councilwoman Linda Barnes Caldwell, D-5th, who wrote a letter in February on his behalf, calling him a “hardworking father” who was “deeply committed to providing for his family,” according to court documents.
“He acknowledges that he has made mistakes in the past,” Barnes Caldwell wrote.
Post-Tribune archives and staff writer Meredith Colias-Pete contributed.
https://www.chicagotribune.com/2025/12/19/gary-drug-ring-head-caldwell-receives-14-years-in-prison/
