Mighele Massey, from Dudley, and Karl Browning and Darren Pegler from Kidderminster were jailed with another man at Worcester Crown Court.
The three defendants and Gareth Pegler, from Wychbold, were sentenced on Friday while others in the case are still awaiting their sentence.
Gareth Pegler, Massey and Browning were all involved in supplying cocaine between 2018 and 2020, with some deals involving over 20kg.
Gareth Pegler, Darren Pegler and Browning were also involved in the cultivation and supply of cannabis.
Following an investigation into serious and organised crime, the four were arrested across 2020 and subsequently charged.
Gareth Pegler, 39, of Saxon Way, Wychbold, was charged with conspiracy to supply cocaine, three counts of conspiracy to produce cannabis and handling a stolen car. He pleaded guilty and was jailed for 14 years.
Massey, 38, of Stourbridge Road in Dudley, was charged with conspiracy to supply cocaine. He also pleaded guilty and was sentenced to seven years and nine months in prison.
Browning, 43, of Hurcott Road, Kidderminster, was charged with conspiracy to supply cocaine and conspiracy to produce cannabis. He was found guilty and jailed for four years.
Darren Pegler, 41, of Coronation Way, Kidderminster, was charged with conspiracy to produce cannabis. He was also found guilty and sentenced to 12 months.
Detective Sergeant Gareth Evans, from West Mercia Police, said: “Drugs can have a devastating impact on communities. (The judge) identified that the supply of cocaine is not a victimless crime - drug supply generates other offences often to support habits or pay debts which impacts on the wider public.
"Vulnerable people are often used to perform roles within the enterprise, with little or no regard for their wellbeing. Gareth Pegler received a substantial sentence that represented the extent of his exploitation of others.
"These sentences demonstrate it is simply not acceptable to be involved in drug crime in any way and we seek the assistance and support of the community in targeting those responsible.
"We urge anyone with any concerns about criminal activity to please get in touch. We review and consider all reports we receive."
Anyone with any concerns can call 101 or visit www.westmercia.police.uk/ro/report. Always dial 999 in an emergency.