Michael Weinstein
I'm a big fan of Bill Simmons and really love what's going on at Grantland. One illustrator that is frequently used for pieces is Michael Weinstein. Once I checked out his work, I was happy to see he has done a bunch of other personal sport projects.
One project was his extensive rebranding of some NBA teams. You can read how he got to these designs on his blog.
Another cool project was his NBA city sport collages:
