The wilderness, whether literal or theoretical, is not a space to be taken lightly. As we learned yesterday, it's a place of intense trial, the duration of which can vary dependent upon how one responds to "humbl[ing] and test[ing]" that takes place there. In the Bible, the trip between Egypt and Canaan was only meant to last eleven days(Deut. 1:2), but rebelliousness and unbelief caused the Children of Israel to wander for forty years (Heb. 3:15-19; 4:1-11).
In this context, what happened to Papa O’Toole in Lost Without You makes sense. Joe’s challenge of Divine Delivery Theory was a rebellious act that exposed his unbelief, demonstrated by the decades of spiritual---and even geographic---wandering explicated here over the past few weeks. In order to be restored physically and spiritually, Joe needed “humble[d] and test[ed]... in order to know what was in [his] heart,” and confront the pain that caused him to go "off trail" decades before. Ironically, the wager placed in the Mailbox Grille that day invited God to begin that work in Joe, his eagerness to prevail in the bet heightening Joe's sensitivity to "something" and ultimately the "miraculous."
Bet On It
Fortunately for Joe, God specializes in the miraculous, and Joe's bet was the invitation He needed to start working. Little did Joe know, he would become part of the miraculous outcome such that he would have no choice but to acknowledge "something" and Oliver's Divine Delivery Theory.
God was trying to get Joe's attention from the very beginning, and orchestrated a highly specific set of circumstances to do so, the first of which was his encounter with the little boy, taking place before the bet was even made. Joe is the only one who ever interacts with him, fielding questions about delivering items covered in peanut butter and jelly, dropped in the street, run over by a car, and torn up in a bike chain. And, of course, it's that little boy, and Topper's destroyed letter, which served as the mechanism through which the entire enterprise here took place.
Notice that when Joe asserts that this same letter "[wasn't] looking very providential," and asks if Oliver coming along on the hike is him "admitting defeat," that Oliver not only rebuffs that possibility, but prompts Joe to inquire about what it sounds like when "something tells Oliver something." The "still small voice" to which Oliver refers is God, creating a connection between "God" and "something" for the remainder of the film. Despite the bit about the "still small voice" being omitted from the U.S. version, it's the only place where "God" and "something" is explicitly connected. Without the reference, the argument is diminished and based solely on implicit references.
It is a good question though: why did Oliver join his father in the woods if he truly believed that the letter was still deliverable?
The answer is because God---not Oliver---was the one really being challenged here. God sent Oliver out with his father (using Shane to do it) because Oliver would never be able to prove that the letter would make a miraculous difference in the world. Oliver isn't capable of performing (or do a good job of recognizing) miracles, only God can. Besides, sending the O'Toole men into the woods together was part of the bigger plan.
"I must have banged a rib...or something."
It was definitely "something" alright. In addition to declaring His presence, God also used Joe's injury as an opportunity to confront Joe with "what was in [his] heart," the puncture wound a physical manifestation of his spiritual ailment, and incurred in the exact place on El Dorado Canyon where he went "off trail" decades prior. Joe had to be "laid low by a scratch"---physically prevented from running away---so that the source of his pain might finally be revealed to him. His damaged relationships may not have felt like "more than just a small cut," but the extent to which the damage permeated other areas of life over time were as devastating as the infection caused by the actual puncture wound. One of those damaged relationships was with Oliver, whom Joe's attempt to reconnect with prompted the bet initially.
But having a new relationship with Oliver required Joe put the past in the past, and correct the wandering behavior that caused him to be alienated from his son. Joe also needed his tendency to put his identity in being Oliver's father corrected. Just as Oliver can't perform miracles, he can't heal Joe in any sense of the word either. Only God was capable of healing these wounds---emotional, spiritual and physical---and He humbled Joe by confronting him with his own humanity to do so.
God was interested in restoring both men in every way, including in their relationship with each other. He even caused Joe and Oliver to travel in a huge circle in the wilderness until they were able to reconcile. They were only rescued after this process was initiated by saying "I love you" to each other.
The most important reference, however, is in advising Oliver as he goes to address "Shane and Dale," both of whom were supposedly waiting in the lobby. "'Something' tells me....you'll know what to say" is, in a sense, Joe not only acknowledging God here, but also suggests that His "still small voice" imparted the knowledge to be shared with Oliver, as if it may have been there deep down inside Joe the whole time.
It's also significant that before he leaves, Oliver turns to say "there has been a lot of leaving in this family, let's not do that anymore." This is Oliver asking his dad not to anything that might cause them separation in the future, and committing to doing the same. Remember it's their separation which prompted Joe to repeatedly invite Oliver to hike or spend time with him. Here Oliver is coming to Joe, when up until this point it has always been the other way around. Taking a step back, you realize Joe not only got the hiking trip, but also the reconciled relationship he desired with his son, despite not winning the bet---a miracle in and of itself.
Wilderness Series: Introduction | Joe | Oliver | Shane | Norman | Prologue