|“||He's no one you'd ever want to meet||”|
James O'Phelan, better known as "Jimmy O", was the leader of the Real IRA group who sold guns to SAMCRO.
Sometime before the events of Season 1, Jimmy O ex-communicated Chibs out of the Real IRA and banished him from Ireland. He then married Chibs' wife Fiona Larkin and adopted his daughter Kerrianne. Jimmy is also responsible for the scars on Chibs' face.
Jimmy O arrives in Charming to repair the True IRA's relationship with SAMCRO, after Cameron Hayes and his son Edmound Hayes started selling to the League of American Nationalists. He personally meets with Chibs and demands that he set up a meeting with Clay. Chibs is initially resistant because of his personal feelings for Jimmy. Then, Jimmy O threatens Fiona's life and insinuates that he has taken a sexual interest in Chibs' daughter. Chibs, however, is blinded by anger and this is used by Agent June Stahl to talk Chibs into ratting out the True IRA. Chibs gives up information on Edmound's safehouse. O'Phelan later avoids capture by the ATF and gives SAMCRO the guns meant for L.O.A.N. for free to make up for Cameron and Edmound's betrayal. He sends a crate containing two dead rats to Edmound, as a message that he knows Edmound sold him out.
In Season 3, Jimmy finds out the truth about Abel's whereabouts, but he feeds Jax misinformation to try and keep up the dealings between the True IRA and SAMCRO. He splits his time between Belfast and Newry, where he is concocting a plan to throw SAMCRO off of Abel's trail. In "Lochan Mor", Father Kellan Ashby meets with Jax Teller and tells him that Jimmy has gone rogue from the Real IRA and is trying to destroy the relationship between the True IRA and the SOA. Ashby promises to give Abel back to Jax, if Jax assassinates Jimmy.
Jimmy tries to have Liam O'Neil, Sergeant-at-Arms of SAMBEL, kill SAMCRO by blowing up a gun shipment in Dungloe that the SOA are protecting, the blast results in the death of 5 SOA members including Chibs' nephew Padraic. While all of this is happening, Jimmy is at the home of Maureen Ashbey trying to take back Fiona and Kerrianne. He ends up killing Michael Casey which he has no problem with. But is stopped by Gemma and Fiona who over power him and his right hand man Donny. Gemma is close to killing him before Fiona stops her. Fiona threatens that if Jimmy came near her or Kerrianne again she would kill him herself. After Liam O'Neill botches the killing of SAMCRO, Jimmy happens to come across SAMCRO torturing O'Neill. He and his men plan to assault and kill the bikers, but are caught in a trap that sees Jimmy and his second-in-command, Donny, barely escape with their lives. Jimmy O and Donny then kidnap and torture Sean Casey for information about Abel Teller's whereabouts. Jimmy executes Sean as a message to the True IRA. He and Donny kill the Irish couple that has Abel and then use the infant as leverage to ensure safe passage out of Ireland and back to California where Jimmy will make contact with the Russian mafia. In a swap at a dock, Jimmy and Donny give Abel back to Jax, but they take Father Kellan Ashby as their new hostage.
Back in California, Jimmy attempts to buy safe passage to Sa South America via the Russian mafia. However, his Russian connection, Victor Putlova, changes his deal with Jimmy and demands more money and a bigger discount on weapons in exchange for smuggling Jimmy out of the United States. Not left with much of a choice, Jimmy has Donny retrieve $712,000 to pay the Russians in advance.
In the Season 3 finale, Jimmy is betrayed by the Russians and given up to SAMCRO, however he is taken into custody by the ATF shortly after. He is then recaptured by SAMCRO and then stabbed to death by Chibs Telford, but not before Chibs gives Jimmy a Glasgow Smile similar to the one Jimmy gave Chibs.