Elizabeth had Neal pegged from the start. In the pilot episode of White Collar, Peter was hesitant to take a chance on Neal. He admitted to Neal that his wife was the one who convinced him. Peter thought it was crazy for anyone with such a short time left on his sentence to break out of prison. Elizabeth said he did it out of love for Kate. Peter told Neal she called him a romantic. Elizabeth was right.
Warning for minor spoilers for the Caffrey Conversation AU.
In the canon series, Neal's romantic side made him vulnerable. It led him to go against his natural instinct and confront Fowler with a gun. Toward the end of the series, a villainess took advantage of his susceptibility. Mozzie was concerned that Neal's romantic nature would get him into trouble and advised him not to wear his heart on his sleeve. (Season 5, Episode 6: "Ice Breaker"). Neal ignored him.
In Caffrey Conversation, Neal has the same vulnerability. His friends at Columbia tease him about it. Klaus Mansfeld cautioned him on numerous occasions about emotional attachments. In the second chapter of Echoes of a Violin, Neal admits that Klaus mocked him for being the Young Man Among Roses. This Elizabethan work by the master miniaturist Nicholas Hilliard depicts a young courtier standing next to a rose bush with his hand on his heart. The Victoria & Albert Museum describes the miniature as being the epitome of the Elizabethan sonnet hero.
By flaunting the theft of Young Man Among Roses just before Neal's trip to London, Azathoth signaled he's also aware of Neal's weakness. It seems inevitable that a master manipulator like him will want to take advantage of that vulnerability.
For further information about the miniature, check out its page on the Victoria & Albert website.
Echoes of a Violin on Archive of Our Own
Echoes of a Violin on FanFiction
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