Parker (Ryan Phillippe) and Longbaugh (Benicio del Toro) are two born troublemakers who travel anywhere they can to find or steal money any way they can. While at a sperm donation facility, they overhear a telephone conversation detailing a $1,000,000 payment to a surrogate mother for bearing the unborn baby of Hal Chidduck (Scott Wilson). Parker and Longbaugh resolve to kidnap the pregnant surrogate, Robin (Juliette Lewis). At the pregnancy clinic the kidnapping of the surrogate mother escalates into a shootout with her bodyguards, Jeffers (Taye Diggs) and Obecks (Nicky Katt), as Parker and Longbaugh leave with her. After the shootout in which two other guards and bystanders are killed, they escape with Robin and elude Jeffers and Obecks, who are arrested. As the fugitives head South, Jeffers and Obecks are bailed out and returned to Chidduck by Joe Sarno (James Caan), a seasoned operative and close friend of Chidduck. As Sarno begins coordinating the rescue of Robin, Longbaugh contacts Robin's gynecologist, Dr. Allen Painter (Dylan Kussman) and orders him to a truck stop to examine Robin.After the examination, Painter returns to Chidduck, and it is revealed that Dr. Painter is Chidduck's son.Longbaugh calls and demands a $15 million ransom for the safe return of Robin and the baby. Jeffers and Obecks, tempted by the money, begin forming a plan to save the child, keep the $15 million for themselves, and kill everyone under the guise of paying off the kidnappers. As Longbaugh hangs up the telephone outside a Mexican motel, he is approached by Sarno, who offers to pay $1 million if they surrender the pregnant Robin and simply walk away. Sarno reveals to Longbaugh that his daughter has something in the works, promising to take care of the old man. Longbaugh declines the offer and returns to his hotel room where Parker and Robin play cards. Sarno then returns to Chidduck's home to relay the events and plan the next step.Jeffers and Obecks realize that Sarno is a wild card in this affair, and Jeffers comes to realize that Robin is Sarno's daughter. Jeffers, Obecks and Painter leave to meet with the kidnappers, while Sarno departs separately with the $15 million ransom. At the motel, Parker is having second thoughts on the kidnapping, he confers with Longbaugh outside the motel room which gives Robin an opportunity to seize a shotgun and barricade herself in the motel room after almost shooting Parker.As sirens are heard in the distance, Parker and Longbaugh hastily escape, and Robin emerges into the parking lot just as Mexican police officers arrive, followed by Jeffers, Obecks and Painter in another car. As Painter and the bodyguards try to persuade Robin to leave with them, the officers pull their guns and order everybody on the ground. Suddenly, Parker and Longbaugh open fire from a nearby hilltop, igniting a fierce firefight that kills the two officers before Jeffers shoves Painter and Robin into his car and drives off, leaving the dead officers and a wounded Obecks in the motel parking lot.Parker and Longbaugh torture the wounded Obecks to gain Robin's location, while Jeffers confines Robin in the room of a secluded Mexican brothel and forces Painter to perform a cesarian section on her to retrieve the baby, despite Robin's confession that the child was conceived between her and Painter and is not Chidduck's. During the operation, the heavily-armed Parker and Longbaugh infiltrate the brothel and search for Robin. The ensuing ambush, that leaves Parker wounded, turns into another standoff with Jeffers threatening to kill Painter and the baby before Painter kills Jeffers with a hidden gun. Outside the brothel, Sarno arrives with a group of bag men and the $15 million ransom, which they stack in the courtyard. Parker wants to kidnap Robin and Painter again, to which Longbaugh, guilt ridden after seeing her condition, says "She's had enough". Despite realizing that the $15 million is bait, Parker and Longbaugh charge headlong into an ambush.All of Sarno's men are killed in the ensuing gunfight. However, Sarno manages to shoot and cripple the already wounded Parker and Longbaugh, and then calls for an ambulance. As a child's cries break the silence, Painter emerges with Robin, newborn baby in her arms. Lying in a pool of blood, Parker and Longbaugh call out to Sarno, informing him that the baby is in fact Robin and Painter's, and thus Sarno's own grandson. Painter wonders aloud if this fact will influence Sarno to let them keep the child. Robin and her baby are then taken away in the ambulance with Painter, Sarno and the $15 million, leaving Parker and Longbaugh to bleed out.Miles away and days later, Chidduck's wife reveals that she's pregnant (possibly from Jeffers, with whom she was having an affair).
Output: Question: Who approaches Longbaugh and offers $1 million to surrender Robin?, Answer: Sarno