What President Trump's Private Prison and Death Penalty Executive Orders Tell Us About Criminal Justice Reform to Come

Adrian Rocha • February 7, 2025

o weeks into  President Trump’s second term, cannabis has not surfaced as a leading issue in the early days of his new administration. However, several appointments and two executive orders signed during the first week of his second term will factor into the new administration’s drug and criminal justice policy approach.


On his first day in office, President Trump signed an
Executive Order (EO) rescinding a slew of EOs signed by former President Biden, including one effectively ending the use of private prisons to house federal prisoners. At the time President Biden signed the EO  directing the Justice Department not to renew contracts with private prison firms, it was estimated that around 14,000 individuals incarcerated at the federal level were being held at private prisons. 


Additionally, President Trump signed another
EO encouraging the Attorney General to “pursue the death penalty for all crimes of a severity demanding its use.”  During his first term, President Trump voiced his support for seeking the death penalty for drug traffickers. This position was later formalized in a memo by then-Attorney General Jeff Sessions that encouraged federal prosecutors to seek the death penalty in cases involving large-scale drug traffickers. There were concerns at the time that the memo could be used to seek the death penalty for individuals involved in large-scale, state-legal cannabis operations; however, these fears never came to pass.


The uncertainty around leadership further complicates the implementation and impact of these two executive orders. President Trump’s Attorney General nominee, Pam Bondi, who will oversee the Justice Department, was confirmed earlier this week. Additionally, the recent resignation of the Director of the Bureau of Prisons (BOP) has left the agency without a leader. During her confirmation hearing, Bonid reiterated her support for the continued implementation of the First Step Act, which could lead to additional releases from the BOP. 


In a letter to the newly minted  Department of Government Efficiency, Senator Elizabeth Warren
(D-MA) also encouraged the federal government to look at scaling back the enforcement of federal cannabis laws, broader legalization, and the BOP to pursue compassionate release at greater scale to reduce the size and cost of the federal prison population. In her letter, Senator Warren cites a potential cost savings of $881 million if the BOP were to more zealous seek the release of individuals over age 65, are classified as presenting a minimum or low risk of recidivism, and are found not to be a danger to the safety of any person or the community.


LPP has successfully advocated for the release of constituents incarcerated for cannabis via commutations and compassionate release motions, including nine in the first Trump administration. If the goal of a second Trump administration is to divert resources away from government largesse, ending unnecessary cannabis enforcement and granting clemency to those still incarcerated for cannabis is a great way to start. 


October 27, 2025
Featuring Carmelo Anthony, Omari Hardwick, Calvin “Megatron” Johnson, and other cultural icons, the NYC event united artists, advocates, and changemakers to advance cannabis justice.
September 24, 2025
NEW YORK, NY – September 24, 2025 – The Last Prisoner Project (LPP) will host its sold-out second annual Journey to Justice Gala on Wednesday, October 15, at Sony Hall in New York City, bringing together artists, advocates, and supporters to celebrate progress toward ending the War on Cannabis. This year’s gala will spotlight the resilience of individuals directly impacted by cannabis incarceration, sharing their stories through powerful performances and heartfelt tributes. Special guests include NBA All-Star Carmelo Anthony , co-founder of Grand National with Jesce Horton, and Brandon “Beedy” Pierce—an agency supporting LPP. Also in attendance will be NFL Hall of Famer Calvin Johnson , Eddie, and Dr. Wendy Osefo of The Real Housewives of Potomac , and comedian and actor Guy Torry , who will serve as the evening’s MC. Additional guests include Jason Flom , Khaliah Ali , and Fab 5 Freddy . The night will also feature a live performance by Joy Oladokun and Bartees Strange and a DJ set by Keith Shocklee , founding member of Public Enemy. “I’m just thrilled to lend a voice to such a noble cause, so that everyone who supports Happy Eddie through purchasing my products will know that no one should be in prison for something that is now legal in many states,” said Eddie Osefo, owner of Happy Eddie . “As we come together as a community to celebrate and advocate for criminal justice reform and lessening social stigmas around cannabis, we must remember to support organizations like LPP that provide prisoner support initiatives aiming to improve the lives of incarcerated constituents by providing them with financial and emotional support during their time behind bars." The gala will honor LPP constituents who have returned home and are now advocating for others. Award recipients include Mario Ramos , who served 13 months for cannabis before opening his New York City dispensary, Conbud, and Deshaun Durham , granted clemency by Kansas Governor Laura Kelly last year, who now champions reform efforts. The evening will also recognize the work of LPP’s Cannabis Justice Initiative (CJI) , which has saved constituents more than 350 years of unjust sentences, including seven life sentences. Additional honorees include Leonel Villaseñor and Jose Sepulveda, two federal clemency recipients who returned home earlier this year. Stephanie Shepard, who served a 10-year federal sentence and is now Board Chairwoman and Director of Advocacy at Last Prisoner Project , said, “The Journey to Justice Gala is a powerful celebration of freedom and the lives forever changed through our work. This year, we’re honored to uplift several of our formerly incarcerated constituents—like DeShaun Durham, who is now thriving and leading in his community after years behind bars for cannabis. Your attendance helps us raise the critical funds needed to support more stories like his. Join us for a night of purpose, progress, and people power.” Proceeds from the sold-out event will directly support Last Prisoner Project’s legal, policy, and reentry programs, ensuring their longevity and impact. Last Prisoner Project thanks its sponsors — Goodwin, DeLisioso, Gotham, Grand National, General Hydroponics, Vladick, Raskin and Clark, Edie Parker, Free My Weedman, Happy Eddie, Primitiv, GTI, iAnthus, ConBud, Ethos Cannabis, BATCH, PuffCo, Sweed, and Ben and Jerry’s— for making this evening possible. Additional thanks go to newly added sponsors Dutchie, Ayrloom, Emerald Dispensary, Flower Mill, 3isFor, and Canopy USA. For more information or to view sponsorship packages, visit the Last Prisoner Project Gala website. For Media Inquiries: Will Mesinger, West End Strategy Team wmesinger@westendstrategy.com | LPP@westendstrategy.com
August 6, 2025
Wednesday, October 15 at Sony Hall in New York City Notable Guests Include Carmelo Anthony, Calvin “Megatron” Johnson, Dr. Wendy & Eddie Osefo, Fab 5 Freddy, Jason Flom & Khaliah Ali, Donte West, Keith Shocklee and Studdah Man of Public Enemy, and Guy Torry with a Performance by Joy Oladokun PURCHASE TICKETS & MORE INFORMATION