"Obi-wan was far too amused watching him struggle to train Ahsoka, and Anakin was more than happy to help Cal cause the Jedi Master some much needed chaos. Or, Cal Kestis loses his master only a few months into the Clone Wars and Obi-wan just so happens to know what it's like to not be quick enough." Somewhere along the lines he gets the foolish idea to train another Padawan.