checkered career
A not-so-stellar past moral/business record of someone who's either a board-game player or a cab driver.
Any taxi-operator who has a history of playing board-games wif his passengers --- either by parking someplace and moving da game-pieces around instead of expediently conveying da customers to where they're going, or even partaking of said sedentary recreation while actually he's behind da wheel, and thus not properly keeping his eyes on da road --- would definitely be viewed as having a checkered career!