did you check html output: does it have <link rel="stylesheet"> tag which points to your file?
Also can you access your css by direct url: http://MySiteCollection/_catalogs/masterpage/Bob/grid.css? Was it published with major version and approved (if approval workflow is in use).
Also you may add custom css to OTB master page without creating custom master page. For doing that go to Site settings > Master page > Alternate css and set link to custom css file there. It will override OTB styles on pages.