Jack Deakins was a former LCPD police officer and former police partner of Frank Murdock. Usually found wearing his favored flowery Hawaiian shirt, jeans and aviators, he dabbled in private investigation work and private security and regularly teams up with his friends Frank Murdock, Harry Brown and Jeffrey Connors to complete assignments. Jack also used to be called 'Skip' by some due to his fondness for the game of hopscotch, he liked the game so much that he became known for carrying chalk around with him. Jack was an avid fan of the classic Chevrolet IROC-Z muscle car. Jack finally left SecuroServ after an altercation with Freddy during which a news reporter was beaten to near death whom Jack befriended weeks before the attack. Jack was dating LSPD cadet Ayda Clarke.
Jack left Liberty City with his former LCPD partner Frank Murdock for Los Santos to set up his own Private Investigation company, and later teamed up with Freddy Price and his private security firm SecuroServ along with Frank.
Jack was loyal to his friends, but was reluctant to break the law unless he deemed it absolutely necessary to do so. He had had an on-again-off-again relationship with SecuroServ chief Freddy Price, and had been hired and fired by the company several times for refusing orders on moral grounds.
After being fired from SecuroServ, Jack teamed up with friend Bobby Irvine to form "Lyrical Limos", a limousine rental company with the novelty act of Bobby singing whilst Jack drove the limousine. The company was a huge failure, failing to attract many customers, and Jack was later convinced by Freddy Price to re-join SecuroServ.
Jack left on vacation to Hawaii for around three months along with close friends Frank Murdock and Jeffrey Connors, after getting frustrated with Freddy Price's increasingly unstable behavior. Eventually Jack and his friends returned to Los Santos and re-joined SecuroServ once again, with Jack joining as a full-time Junior Agent. Whilst Freddy Price was out of town, Jack decided to set up the "SecuroServ Bicycle Division" (SSBD), wearing a SecuroServ uniform along with short-shorts and cowboy boots whilst riding a black bicycle with red-wheels, gaining much attention and ridicule.
Jack left SecuroServ along with friend Legs Macready, to form his own security company named "Justice Security" after falling out with Freddy Price once again due to his questionable morals. Jack decided to visit a local strip bar one evening and was knocked unconscious by a local man. In a chance encounter, Ayda Clarke found him outside on the floor, and called for an ambulance. When dating her, Jack refered to Ayda as "my Angel".
After failing to attract security customers he attempted to re-join SecuroServ as a confidential informant for the LSPD. This failed however, and Jack was subsequentially shot three times in the back by friend Jeffrey Connors after a failed kidnapping. Surviving thanks to his bullet-proof vest and fearing for his life, Jack went into hiding to elude SecuroServ, sporting a number of disguises.
Kidnapping and Murder
On March 6th 2018, Jack was contacted by Frank Murdock by text wishing to arrange a meeting. After spotting Freddy Price's car drive into the parking lot earlier in the evening, and fearing a reprisal for his girlfriend Ayda Clarke shooting Freddy whilst on duty the week before, Jack and Ayda decided to inform the San Andreas State Police before-hand of the meeting with Frank.
Jack and Ayda drove to meet Frank at Mirror Park. After a few minutes of talking, Frank pulled out a gun and forced them to drop their weapons and phones. SecuroServ members Freddy Price, Jeffrey Connors, and Mike Lemonade then pulled up with a large box truck, forcing and locking the couple in the back storage area. Freddy along with Frank drove the vehicle to the top of Mount Chilliad, with Freddy taunting Jack that it had been a long time coming, remarking that it was a punishment for Ayda shooting his wife Fanny Price the week previous.
Jack reminded Frank that his daughter Lily Murdock had been brutally murdered by Richard Oakes in the mountains and that he was aligning himself with another psychotic individual in Freddy, but he was ultimately unsuccessful in persuading Frank to help them. After being joined by Jeff at the top of the mountain, Freddy rolled the truck over a cliff with Jack and Ayda inside, managing to injure himself in the process. Jack died in the resulting explosion, though girlfriend Ayda Clarke managed to survive.