Madeline Pratt trusted Raymond Reddington just about as far as she could throw him.
She wasn't a fool. Just because she happened to think the man was sex on legs didn't mean she ignored his reputation. He was loyal only to those who were loyal to him. As fond of him as she was, she certainly couldn't count herself as part of that group; she looked out for herself first and foremost, before anyone else.
For a long time, she thought the same was true about Raymond, which was part of the reason she considered them so well-suited to one another.
So, no, Madeline Pratt didn't trust Raymond Reddington any more than he trusted her, and he didn't trust her very much at all. (He trusted her with his trouser belt, with being able to walk the fine line between pain-as-pleasure and plain old torture, but that was really the extent of it.)
Perhaps she trusted him less than that, even.
When Raymond promised to meet her in Florence, Madeline had him followed. She had many eyes and ears around the world, much like he did. She considered the possibility that he wouldn't show—he was, after all, one of the flightiest men she'd ever met—but she hadn't considered why.
And so on that cool August day, when her people sent her video footage of him as he strode into the J. Edgar Hoover Building with such purpose and determination, she recognized it as the beginning of the end. That it happened on the day he promised to meet her only served to rub salt in the wound.
Raymond was smitten with the girl, eager and preening and downright pathetic. He showed off like a school boy, tried to impress her with his quick wit and his connections. He held her hand and comforted her while her life fell apart around her.
And the worst part of it all? The girl didn't realize what she had in front of her. She still went home to her husband every night, despite evidence that the man wasn't who he claimed to be. Madeline had half a mind to uncover his duplicity in no uncertain terms and wave it in the girl's face, but she ultimately decided to sit back and see how everything played out.
In the meantime, she devised a test for Raymond; Madeline had to see the girl for herself, if only to see if she could decipher what the hell made her so special.
'Nicole' surprised her, but then again, she should have expected Raymond wouldn't be interested in just any FBI agent. If that was all he wanted, surely that blond beefcake would've sufficed.
A thief and a pickpocket. Madeline was pretty confident they didn't teach those skills at Quantico.
If the heist hadn't been a setup, she was sure the girl would have gotten away clean. If she wasn't FBI, if she wasn't Raymond's pet, Madeline would seriously consider taking her on as a protege.
Fate. What a ridiculous thing for Raymond to say. What an insult. As if whatever superficial connection he had with the girl could even hold a candle to what was between them. She and Raymond had history.
For a year, Madeline had been trying to come up with a way to pay Raymond back for taking advantage of her sympathy. The King auction was a stroke of inspiration; orchestrating her own abduction was an ironic touch she just couldn't pass up.
A setup for a setup, a play for a play. Fair was fair.
Either Raymond would somehow get himself out of it like he usually did, or he wouldn't. At this point in their relationship, she was at peace with either outcome, really.
Everything at the auction ran smoothly, right up until the point when it didn't. Word got out of an undercover agent on the property—young, beautiful, FBI. Before she was made, she bid exorbitant amounts of money she surely didn't have on Raymond Reddington. She lost the auction, but created a spectacle before disappearing into the crowd, a distraction that Raymond gladly participated in.
Only two cages were empty when the feds stormed the compound: the kidnapped Peretti boy's and Raymond's. The man who won Raymond was found dead on the cold tile floor with a bullet in his brain. The old man King was dead as well; rumor had it he was shot through the heart by Raymond himself, generations of a dynasty put to rest with a single bullet.
Perhaps Raymond and the girl were a force to be reckoned with after all. Madeline looked forward to finding out.
