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Over the years Jones noticed that Neal would sometimes mention things that were vaguely concerning. None of the individual ‘incidents’ would have stuck in his mind, but they kept happening, one after the other. It was well known that Neal had a rough childhood, but most people assumed it was simply due to his parents dying when he was nine (a fact that the conman had willingly shared).
The first interaction that had truly bothered him was when he and Caffrey were both getting coffee, and Neal offhandedly mentioned doing something with a brother.
His eyebrows immediately shot up, “Brother?”
“Uh, yeah.” Neal said, quickly shooting him a sideways look.
He poured a packet of sugar into his coffee before turning to face Neal, “I didn’t know you had a brother.”
Neal’s eyebrows scrunched, “Huh… I would swear I mentioned my family at some point.”
Jones shrugged, “Only your parents.”
Neal’s face cleared, “Ah… Well… I have a-” He paused, “...pretty big family.”
“That’s cool,” Jones said; that was the extent of their conversation.
The second time was when the office was helping Organized Crime with an overload of cases.
They’d been looking over their current case for not even a full five minutes when Neal spoke up, “It’s revenge. I’ve seen it before.”
Neal spoke quietly, but the entire room’s attention immediately shifted to him. He continued, unbothered, “This guy’s hurt and he wants the people around him to feel his pain.” His face scrunched up, as if remembering something unpleasant, “He’s suffering.”
When Neal looked up a minute later, he seemed surprised that everyone was staring at him.
“What the fuck Caffrey?” Diana asked.
Neal grinned sheepishly and rubbed the back of his neck, “Just one too many true crime documentaries, I guess,” he said with a good natured laugh.
In the end, Neal was right. The man had been on a revenge mission, and was definitely suffering.
It happened again during ‘take your kids to work week’.
They’d all been focused on work, when suddenly a shout rang through the air, “The floor’s lava!”
It was a young girl, probably seven or eight. Some of the adults chuckled and moved to humor her, but not Neal.
Jones heard a noise above him and looked up slowly to see the conman perched precariously on a filing cabinet above him, eyes wide and panicked.
From off to the side, Peter sighed, “Neal, what in the world are you doing? Get down.”
Neal seemed to take a few seconds to compute before he quickly scrambled down, grinning sheepishly, “Sorry, Peter. When my family plays games like this; they take it…” He hesitated, “-very seriously… Like… way too seriously.” Neal laughed, but his eyes were dead serious.
So, yes. Jones was concerned about Caffrey’s past.
Neal had a big family who took things very seriously, and he seemed to have some sort of personal connection to a case involving revenge killing. When you put together all the elements, there was really only one possible solution; Neal came from some sort of crime family.
It sounded ridiculous, but it made sense. It explained why they didn’t know anything about him until he turned 18 and lined up with all the things he’d said over the years.
After some serious consideration, he decided to keep it to himself. If it was true, Neal had gotten away, which he knew was insanely difficult, and bringing it up, especially in any official capacity, could put Neal on the map and draw dangerous attention to him.
It wasn’t until later, after finding out the truth about everything, that Jones brought up his original theory about ‘Neal’s’ family, and after several minutes of laughing, Dick admitted that he could see how Jones would have drawn that conclusion.
Neal played dumb when it came to weapons; Diana was sure of it. She didn't have any solid proof, but the facts spoke for themselves—and, by god, that man was way too good at laser tag.
The office had to run a mandatory team building exercise, which Peter put up to a vote, and they chose a laser tag facility. By the time the game was finished, not a single person claimed to have seen Neal, but the scoreboard showed he'd taken out over half the people participating.
Later that day, when practically the entire office had stuffed themselves into a small pizza restaurant about a block away from the lazer tag place, she cornered him by the bathrooms and asked how he’d done it.
Neal shuffled his feet and rubbed the back of his neck. “I found a good hiding spot and then just waited for people to walk by. I’m honestly kinda surprised at how well it worked. I guess nobody was on the lookout for me because I’m nonviolent and all.”
She’d accepted the answer, but something still felt off about the whole thing.
It wasn’t long after that when she noticed Neal had ‘the hand twitch’. The unconscious response that anyone who regularly carries, or used to carry, a weapon has in dangerous situations; the automatic twitch of the hand towards a belt or jacket where one might expect to find a holster.
The first time Diana had noticed it, she thought she must have just imagined it. Neal was, after all, well known for his nonviolent tendencies. The second time though, she had to admit to herself that it was true.
She watched it happen a third, fourth, and fifth time, until it began to become normal; just another part of who Neal Caffrey was. He knew guns, but judging all the wide variety of directions his hand would twitch—hip, thigh, ankle, jacket—he probably could wield a much more varied arsenal than that.
But even knowing all that, she decided not to say anything.
First, there wasn’t definitive proof of anything. Second, Neal had no record of violence. Third, the man was her friend, and even if he had those instincts, it might be something that he’d made a choice to get away from, which she could respect; everyone has a past.
Over the years she forgot that it wasn’t a known thing, Neal’s history with weapons, which was why when she and Neal found themselves alone in a very dangerous situation she threw him her spare firearm without a second thought, not even considering that he might not catch it or be baffled as to why she was giving a loaded gun to a nonviolent convicted felon.
He caught it, of course, and together the two of them easily handled themselves (not a single casualty), but the second the last man fell he turned to her with a baffled expression. That was when she realized what she’d just done.
Diana had just shown Neal that she’d known about his ‘secret’ weapon capabilities.
Panic in his eyes, Neal spoke, “This isn’t what it looks like!”
She shrugged, “Don’t worry about it Neal.” She plucked the gun from his hands and strode out of the building, leaving him standing behind her, no doubt baffled.
From that point on, every time he tried to bring it up, she’d refuse to speak on the topic, either quickly changing the topic or simply walking away mid conversation. They didn’t end up actually speaking of it until many years later, after several of Dick’s other secrets—ones that explained quite a bit—came to light.