There is an on-going joke all these years, since the release of the original Resident Evil 2 in 1998, that Albert Wesker might have been secretly lusting over Rebecca Chambers, because of an easter egg included in the game, which was also present in its recent remake in 2019. In the S.T.A.R.S. office, the boss naturally had his own private space where his desk also was. One of the drawers in his desk used to hold a little secret. In the original game, you had to interact with it 50 times, and then you would be rewarded with a special film roll.
You then had to take the film roll down to the Dark Room and develop it, to find out it was actually a photo of Rebecca in a rather playful pose, dressed in basketball outfit with the R.P.D. logo on her top.
There is no prompt to interact with it; you can take it, however, and when you do you can see that it has the phrase "Rising Rookie" written on it.
There is this fan theory which claims that Wesker was a creep and liked to keep a photo of Rebecca in his drawer because he fancied her. Personally, I never had such an impression, and I was convinced right from the start that Wesker had, in fact, nothing to do with Rebecca's photo. Wesker cared only for power and had little to none interest about anything or anyone else, let alone a timid, awkward - at the time - rookie, who moreover was more involved in the medical field and was not much of the action type. The fact that the film roll, in the remake, is hidden at the back of the drawer further hints that it probably was not placed there by Wesker himself. You could say all sorts of things about Wesker, but as far as this kind of creepiness is supposedly hinted here, it feels way too out of character for him. The way I saw it, someone from his team purposely put the film roll there either to prank him or to make him look like he was indeed a creep. Or maybe to prank Rebecca - since she was notorious for her naivety at the time - by making her believe that the boss fancied her.
In the very recent Resident Evil Requiem, during Leon's nostalgia trip around the ruined R.P.D., our hero discovers a series of playful clues which were part of a treasure hunt organized by Barry Burton, obviously some time before the Spencer Mansion incident. Barry had set up several puzzles so as to tease his younger colleagues by having them searching around the police station to find the rewards he had hidden for them. Among the clues, is Barry's list of things he had to do, where he had noted that it's a top priority to find a missing book which was last checked out by the captain (meaning Wesker). Although this looks like it was Barry's personal list, it was left in plain sight on his desk, so that anyone could see it.
Then in Wesker's drawer, the same where the film roll was in Resident Evil 2, Leon finds the Library Card which reveals the title of the missing book (Medicinal Benefits of Herbs) and lists the people who had borrowed it, with Wesker indeed being the last person to have it (interestingly enough, he kept it only for two days).
Then Leon can go to the Library and find the book on a shelf of the upper floor.
When Leon opens the book, he finds the infamous photo of Rebecca inside.
It is insinuated that Wesker borrowed the book from the Library and somehow "forgot" Rebecca's photo among its pages when he returned it. Or at least this is how the facts make him look. Knowing his personality, however, it is highly unlikely that he would walk around carrying Rebecca's photo, randomly leaving it here and there without taking notice, especially if he was - supposedly - interested in her. In reality these new facts from Requiem hint even more that it was never Wesker himself who had put Rebecca's film in the drawer of his desk, and most probably he had no idea of its existence.
With all the new elements at hand, seeing now how Barry used to play around with his colleagues, and considering that one of his puzzles mentions specifically the Library Card with Wesker's name on it, it is highly possible that it was Barry who, back in the day, hid the film roll in Wesker's office and, subsequently, the developed photo in the book that Wesker had borrowed from the Library. Come think of it, he knew Wesker's moves with every detail, knew that is was him who had the book last. Supposedly Barry did now know where it was (therefore the note about the "missing book"), but what if it was him who had secretly taken it, after Wesker had returned it, so as to specifically hide Rebecca's photo among its pages, then put it back on the shelf and indirectly urge the others to look for it by leaving his To-Do list on his desk, thus making it known to everyone that it was the captain who had the book last, so that whoever eventually found it, would see Rebecca's photo and infer that it was Wesker who had left it there. Barry was a good man but, as is revealed now in Requiem, he also loved to fool around and tease his colleagues, and he would probably make no exceptions for his boss either. Not exactly unexpected from an old dog like him!









