|Portrayed by J.R. Bourne|
|Parents:||Joe Ryan † (father)|
|Siblings:||Nate Ryan † (brother)|
Kenneth "Kenny" Ryan is the new owner of the Stowaway that has bought it for a personal vendetta against the Porters.
Kenny and his brother, Nate, were the sons of Joe Ryan, a racketeer in Montauk whose gang extorted "protection money" from local business owners. He was shot and killed by Matt Duncan using Carl Porter's gun in 2006 after arranging a hit and run that put Matt's daughter in a hospital. Consequently, his sons, who were also criminals and knew that he was meeting Carl the night he was killed, wanted payback.
In "Confidence", we see Declan and his new troublemaking friend, Trey Chandler, breaking into a house in Southampton and taking jewelries. Working with Trey, he then goes to Jack Porter and tells him that he apparently caught the thiefs running away from his home that night and shows him Declan's driver's license. After they both confront Declan, who refuses to sell out his other companion, he settles the argument between the brothers by saying that he won't press charges if he gets his stuff back. Jack says he owes him a favor, and Kenny says he's "going to hold [him] to that." Unfortunately, in "Intuition", Trey tells Declan that the loot has already been sold and the buyer won't return it. It is revealed that Kenny and Trey have been in cahoots the whole time and have arranged the robbery as part of a plan for Kenny to be able to pressure Jack into making him co-owner of the Stowaway.
It was revealed in "Lineage" that Ryan's desire to take over the Stowaway dates back to the death of his father, a local criminal, which he and his brother believed was caused by Jack and Declan's father.
Later, when his brother, Nate finally comes by to meet the Porters, he expresses reluctance with their plan, saying that the Porter brothers are good people.
When Kenny and Nate find out that Matt Duncan is coming to the Hamptons for Carl David Porter's christening, they get him alone and beat him up to get him to tell them what happened to their father. Nolan also finds out and tells Jack that it was not his Southampton home that Declan and Trey had stolen from before and he is actually only subletting a one-bedroom apartment in Sag Harbor.
In "Collusion", Conrad, after an agreement with Jack, buys the Ryan brothers' share in the Stowaway, remarking that the Porters have been put through enough. Kenny, apparently satisfied, accepts even though Nate still wants payback.
Afterwards, Nate makes a deal with Conrad to steal the laptop Amanda is using to blackmail Conrad and then get the Porter couple out of the way. While attacking them at the Amanda, Nate is killed in a propane gas explosion after injuring Jack. Nolan saves Jack with a boat he bought and then alters the paperwork to make it look like Kenny is the owner.
Kenny reemerges in "Victory" after being lured out by the Porters. While being questioned by Jack, he truthfully denies owning a boat and reveals that Nate kept recordings of his conversations with Conrad.
Kenny is a "magnetic, self-assured Hamptons resident who tries to hide his rough edges behind his fancy clothes and Mercedes".
Although prepared to commit crimes and smuggle drugs Kenny lacks the determination to persue his efforts if he feels there is no point. This is shown when he learns of the confession to the murder of his father when Conrad buys him out of ownership to the Stowaway. Kenny acts as the partner in crime with his brother Nate, however it is Nate who is the more controlling of the two brothers demanding they continue with their plans both when Kenny sold the Stowaway and when Kenny grew to like Jack and Declan.
Kenny has been shown to be very forgiving of certain people. After he receives Matt Duncan's confession and a check from Conrad, Kenny immediately decided he was satisfied and (unsucessfully) tried to ask Nate to move on. After Nate's muder-suicide, Kenny gave Jack a recording of Nate and Conrad's conversation that ultimately lead to Amanda's death.
Whereas his brother was clearly villainous at any time, Kenny on occasion offered sympathy to the Porters such as to Declan after Jack was arrested when Nate planted drugs on the Amanda framing him.
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