Jesse James Hollywood the Alpha Dog Killer — True Crime

Jesse James Hollywood the Alpha Dog Killer — True Crime

A teenager starts a crime empire and watches it all fall apart with ill-made plans of murder.

Image for postPhoto by Matthew Hamilton on Unsplash

Teenage Crime Boss

At the age of 19, Jesse James Hollywood was already a crime boss. He had purchased an upscale home in the West Hills, drove a black Mercedes, and had non-stop parties. Hollywood achieved it all by being a marijuana distributor.

Image for postPhotos of Jesse James Hollywood | via Murder Files

But as with every business, there are downsides. The start of the end for Hollywood was when one of his dealers and a friend, Benjamin Markowitz, owed more than he could pay.

Benjamin Markowitz owed over $1,500 to Hollywood and didn?t appear to be ready to pay it back any time soon. Then one night at Hollywood?s house, Benjamin Markowitz broke a window; this was the last straw for Hollywood.

Image for postBenjamin Markowitz | via WikiFandom

Change of Plans

Hollywood decided he was going to get Benjamin Markowitz to pay his debt one way or another.

On August 6, 2000, Hollywood planned to ask Benjamin one last time, face-to-face, for the money. And if Benjamin didn?t hand it over, he was going to kidnap him and make his family ransom his debt.

But, on the way to find Benjamin, Hollywood came across the younger brother, Nicholas Samuel. And for whatever reason changed his mind, and took Nicholas instead.

Along with Hollywood was Jesse Rugge and William Skidmore. The three took Nicholas to a friend?s house to lay low. Others came and went from the place, and would later say that Nicholas didn?t appear to be a hostage, that he was free to roam about and was treated like a guest.

During the days he was held, Nicholas even went with different people to house parties. Teens and their parents said they had seen the boy, and none of them thought he was being held against his will.

Meanwhile, brother Benjamin still wouldn?t pay his debt, not even when Hollywood threatened to hurt Nicholas. Hollywood had assumed Benjamin would pay. He never expected the brother to call his bluff.

Hollywood knew he was in trouble and contacted his lawyer to talk about his options. His attorney told him that he could be facing a life sentence for kidnapping Nicholas. Now is when the plan took another turn for the worse.

No Going Back

Hollywood decided that the problem, Nicholas, needed to go away. He gave a TEC-9 to some associates and told them to take care of Nicholas.

Ryan Hoyt and Jesse Rugge took Nicholas out into the Santa Ynez Mountains. He had no idea what was going on until they happened upon the freshly dug grave along the Lizard?s Mouth trail.

They then duct-taped Nicholas?s hands and put tape over his mouth. They hit Nicholas in the back of the head with a shovel, causing him to fall into the hole and then shot him nine times in the torso and head. In an attempt to get rid of the gun, they buried it with the body.

Nicholas?s body would be found six days later.

Four of the accomplices that helped Hollywood, Ryan Hoyt, Jesse Rugge, Graham Pressley, and William Skidmore were arrested and charged with murder.

But the crime boss Jesse James Hollywood was in the wind. Police tracked him to Colorado Springs, Colorado, but again he was able to get out of town before being arrested.

Image for postImage for postJesse James Hollywood mugshots | via Wikipedia

New Life

After five years on the run, Hollywood was found living in a Brazilian resort community outside of Rio de Janeiro. There he was living with his pregnant girlfriend and going by the name Michael Costa Giroux. He was working as an English teacher.

Hollywood thought that he couldn?t be extradited from Brazil if he fathered a child there. Unfortunately for him, that law changed, and also it didn?t apply to him since he had come into the country on a fake passport.

An interesting fact, the day Hollywood was arrested in Brazil, his father Jack Hollywood was arrested in the US for manufacturing GHB.

While in jail awaiting trial Hollywood started signing all of his mail ?Alpha Dog? and said that when he got out, he was going to take an ?Alpha Dog World Tour.?

The movie titled Alpha Dog was released in 2006, which retells the story of Hollywood and the murder of Nicholas Markowitz.


Ryan Hoyt was convicted of first-degree murder and sits on death row at San Quentin State Prison in California.

Jesse Rugge was given a life sentence but has since been paroled in 2014.

Graham Pressley served five years for second-degree murder and was released in 2007.

William Skidmore served nine years for kidnapping and robbery and was released in 2009.

Image for postMelinda Enos Hollywood (left) and Jesse James Hollywood (right) | via The Independent

In July of 2009, Hollywood was convicted for the murder of Nicholas Markowitz and was sentenced to life imprisonment without the possibility of parole.

Jesse James Hollywood currently resides at the Richard J Donovan Correctional Facility in San Diego, California. In 2014 he married Melinda Enos. She had begun writing to him after he was convicted.

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