I'm with the people saying you should probably just buy it now. While I don't work for Walgreens (and due to competition reasons I rarely shop at Walgreens; only when I need something my store doesn't sell), I do work for a grocery store chain in the Midwest, and my dad is actually in charge of all of our nonfoods merchandise, as well as candy/seasonal products, so I grew up surrounded by situations like this and work in them now.
Since it is a Valentine's Day item, once the store runs out there is no getting more in. If it was a month ago, there might've been a chance of them getting another shipment, but with only two weeks till Valentine's, they won't reorder it.
Walgreens *should* start discounting by the 15th. My store usually starts discounts on seasonal merchandise the day of the holiday (or, in the case of Christmas, late afternoon on the 24th). The reasoning behind this is that most stores receive their next seasonal set before the end of the previous holiday (like at our store, we've had Valentine's M&Ms out since the week before Christmas), and want to turn over quickly to maximize profit on each holiday. My dad will be marking down some Valentine's merchandise late next week/early Valentine's week (the stuff that normally doesn't sell), the majority of it on Valentine's Day, and anything not marked down by Valentine's Day will be moved late that night and marked down. The Easter set goes up overnight on the 14th--actually, we've already got standing displays scattered in a couple places in the store with Cadbury eggs and Reese's Peanut Butter Cup Easter eggs. I would be very surprised if we had any of our Valentine's merchandise left by the 16th, and we'll probably do serious markdowns if there's anything left by the 17th or 18th--but we're not expecting much left.
Like a PP said, a lot of people wait till the very last second to shop for Valentine's Day. And at that point, a giant teddy bear looks very appealing (aren't they always?). Our store is already running out of certain Valentine's Day stuffed animals, and we're still two weeks out. I would be very surprised if any made it past Valentine's Day.
So, yes, if you wait on the bear, it will be discounted after Valentine's Day--but that's only if it makes it to the day after Valentine's Day. If you have your heart set on this bear, buy it now. Personally, what I would do is talk to a store manager and get an estimate of how many bears they have left, then make my decision based on that number. If they have a pallet of teddy bears in the back room, no reason to purchase it now. If what's on the shelf is all that's left, immediate purchase is your best bet.
I will add that if you miss out on this teddy bear, Easter should be the next holiday set (unless your store does something for St. Patrick's Day; mine doesn't really), and Easter often brings cute stuffed animals, too. So if you do hold off, and they run out of bears, you might find something even better in their Easter merchandise.
