Castle Wiki
Winston Wellesley
Wikia Castle - Winston Wellesley
Vital Statistics
Gender Male
Status Alive
Parents Lenanne Wellesley (mother)
Casper Wellesley (father, deceased)
Other family Blake Wellesley (brother)
Unnamed brother (deceased)
Trent Wellesley (nephew)
Olivia Debiasse (niece, deceased)
Character Information
Appearances Kill the Messenger
Portrayed by Gregg Henry

Winston Wellesley greets Beckett and Castle's line of questioning in "Kill the Messenger" with all the condescension one would expect of the scion of one the Big Apple's great families and a member of New York's de facto royalty.

Winston's name came up in the duo's conversation with his nephew, Trent Wellesley, who in turn may be connected to a cold case which is somehow relevant to the death of bike messenger Caleb Shimansky.

Winston himself, ten years on from the evening in question, can apparently remember little about Olivia Debiasse, implying that she was a fetching little thing who was simply part of the night's 'entertainment'. As the investigators dig deeper, however, the picture changes radically.

Winston is the son of Lenanne Wellesley, a matriarch in the Rose Kennedy mold, who runs her family with an iron fist and only occasionally bothers to conceal it with a velvet glove. At least, she did. Mother's faculties aren't what they were, and Winston is not the favored child, so his brother Blake acquired power of attorney. Winston, however, was desperate to be 'of use' and still did his mother's bidding in almost all things, having 'failed her' in an essential - he's a homosexual, a fact he's careful not to advertise. This gives the lie to his original depiction that Olivia was his 'dish of the day'.

Blake, as a candidate for Senator, has attempted to use his influence to 'suggest' that the 12th Precinct should conduct their investigation under his aegis, something Captain Montgomery equally politely refused to do, but eventually he and Winston are brought in together to the interrogation room.

As it emerges that Winston and Mother kept much from him, the bombshell in which is that Olivia was in fact his daughter, Blake ignores Winston's warnings and airs the family's dirty laundry. All of which leads back to Lenanne, and in turn the killer.

However, while Winston was willing to perpetuate many lies to protect his brother's image at his mother's behest, including that he, not Blake, was Olivia's father, he had no involvement in the murder case that Lenanne kickstarted 10 years ago.