This sad little bear is modeling Karen's new winter cap, a Koolhaas, so you can see it. She didn't want to model it, so poor Mr. Sad Bear was rushed into service.
Mr. Sad Bear was my mother's when she was a child. According to the story, she went with her father to the local landfill in Iowa and rescued him from the pile. All of his fur was matted, and what wasn't matted was threadbare. He had seen better days, though I imagine Mr. Sad Bear would have been hard pressed to remember them. I inherited Mr. Sad Bear when I was little. He was unimpressed, and continued to be sad. (You'll also notice that I had a very sophisticated naming scheme for things as a child.)
Almost every time Mr. Sad Bear makes an appearance, Karen ends up crying a little about his rough life. I suppose he should have known it was going to be rough, being made with a built-in tear—which has long since lost all of its blue paint.