Anderson has played just 90 NHL games in his career and just hasn't been able to stick and carve out a niche for himself. Surprisingly, Anderson has been pretty dominant at the AHL level, having recorded 27 points in 30 games this season and 42 points in 56 games last season, both with the Toronto Marlies. However, with just 3 points in 14 games this season with the Leafs and 5 points in 18 games with the Blackhawks, Anderson just isn't doing enough to warrant keeping his roster spot.
In terms of whether or not he'll be claimed, there certainly is some upside there. Anderson is a hard-worker and is still just 24, but he appears to be caught in this weird spot of being too good for the AHL but not quite good enough for the NHL. Hopefully he does get another opportunity, whether that be in Chicago or elsewhere and if/when he does get that opportunity, hopefully he can make the most of it.