Risk (2000)

Young Ben Madigan (Tom Long, THE DISH) has just become an insurance adjuster out of a desire to help people. When he joins the firm, however, he falls under the wing of seasoned and unscrupulous veteran adjuster John Kriesky (Bryan Brown). Preying on Ben's naivete, Kriesky embroils him in an elaborate plan to defraud the company and line his own pockets. Making involvement even harder for unsuspecting Ben to refuse is Kriesky's sexy and willing girlfriend Louise (Claudia Karvan, ATTACK OF THE CLONES), a shady lawyer who aids Kriesky in his scam. When Ben finally realizes what he is involved in, he is already in over his head--both personally and professionally.