This is the Gospel passage that most people of my particular vocation (mainline, generic, Protestant pastor) try to preach on every three years at about this time, as the twenty-eighth "Proper" after Pentecost, traditionally known as "The Parable of the Talents." And when we do so, we traditionally tend to fumble it badly. The (alleged) allegorical first part is a problem (why would Jesus tell a story about his going away and coming back to judge us, when most of his listeners had no clue that he might eventually go away). And the brutality of the concluding part is a problem (why would Jesus destroy someone and cast him into outer darkness just for not following orders?). So, we wind up preaching something that is sweet and supportive, but also fairly mushy and toothless.
Today I'm more and more inclined to think that it actually has very little to do with "talents" as we know them (singing, dancing, selfie-taking, etc.) and much more to do with money and banking and oppression and power, and also one poor, faithful, schlep who stood up to it all and took a hit for it. That may sound a little strong, but given the First Century transactions by wealthy people with real "Talents" (that is, with money), I think it may be a lot closer to the original intent of Jesus.
Let's start with the money. Most of what we would think of today as commercial trade or "investing" in Palestine was done by the wealthy one percent--meaning rich people, royalty and the priests (who took in and spent investments held in the temple, and then traded with them for foreign goods and currency).
There were two common ways that one with sufficient capital could make a profit from investing. The first was by lending to those involved in the currency exchange business in the Temple. When Jews or others came to Jerusalem from other parts of the world, they needed to change their international currency into the local Jewish currency, and the exchange tables served this purpose. International Jews in particular (and there were many) needed to make a sacrifice in the Temple, but typically only carried Roman currency, with the Emperor's picture on it, so they exchanged it for local currency, which did not (remember the story of Jesus and the coin with Caesar's picture on it?). A wealthy person's investment in this, from fees and exaggerating the exchange rate, could be very high.
The second form of investment was in mortgage loans or bridge loans to small farmer families struggling to stay afloat in the declining first century Palestinian economy. Most loans made huge returns on their investment because interest rates were so astronomically high by today's standards--anywhere between twenty-five to fifty percent. (It's worth noting in this regard that one of the causes of the "lost decade" of the 1980s, for poor and developing countries of the global south, was that the interest charged by banks in the "First World" on loans to countries in the "Third World" rose sometimes to as high as twenty-seven percent.) The purpose for loans then, was primarily for the purpose of getting borrowers in over their heads and then being foreclosed on and losing their property. They would then either become tenants on what had been their own property, or homeless, or join the ranks of the growing number of bandits or revolutionary militias.
You noticed a similar thing happening in southern Mexico (and elsewhere) during the mid-1990s, when the rules of NAFTA allowed the government to stop issuing credit to poor coffee farmers at just the same time that the prices for coffee collapsed to an all-time low. The result was hundreds of thousands of families losing their homes and their farms and becoming beggars, or fighters, or sweatshop workers, or immigrants into the US, fueling the immigration issue decades later that has Congress inflamed today.
Much of the income from the first century loans was deposited in the Temple to keep the rich from having to pay a Roman tax on it, and to keep them from officially being the holders of the debt when the Sabbath and Jubilee-debt-cancellation years rolled around (a law called the "Prosbul" allowed them put their money in the Temple just before the seventh year, to claim they were no longer able to cancel the debt). And then the money was often invested elsewhere by the priests who were the financial overseers of the "bank's" holdings. There are a number of ancient inscriptions that show Priests investing in trade and commodities using this "tax-sheltered" money drawn from mortgages taken out by poor families in rural Palestine. That's probably one of the reasons why Jesus decided to occupy the Temple and set up a temporary boycott of currency trading there as his first official act in Jerusalem. And it is clearly the reason why--when the revolution finally came--the angry 99 percenters stormed the temple and burned the mortgage papers that had been held there.
It was also common, as this parable indicates, for wealthy lenders to assign the dirty tasks of originating the loans, collecting on them, and then repossessing the properties, to their servants. It was considered dishonorable for nobility to expand their wealth, and since servants were a class without honor, they were given the job. That gave the lenders the ability to deny any knowledge of wrong-doing if an evicted family's misery became too public. The story of the widow and the unjust judge is something similar to this (Luke 18:1-8, Proper 24 C).
It's also important to add here that the servants who were entrusted with inflicting this pain on people didn't do it necessarily for monetary gain (because they usually weren't paid anything), but instead they did it for the power and prestige they received for successfully managing the company. As the parable says, if they were successful in little, they would be given power and responsibility over much. The lead character in the parable of the Dishonest Steward plays a similar role. Also reflected here is that interest rates were often as high as fifty percent, so it would not be at all unlikely for a steward of a powerful finance family to double or even triple an investment.
In this story, servants one and two clearly went along with this insidious system and were rewarded handily for their efforts. The first put his money into trading (ergázomai, probably commodities because they were the most frequently traded at the time), and the second used interest-bearing investments (kerdainō, like the loans and currency-trading mentioned above), but both made a healthy profit.
But the third person (often the hero in three-part tales), following the Torah that forbade lending money at interest (Exodus 22.20-30), believed that the system was corrupt, that the leader was evil, that money should not be used as a weapon against homes and farms and families, and he refused to participate. He accused the wealthy one percenter of being a "sklēros," someone who is violent, rough, offensive, and thoroughly intolerable. He accuses him of not actually doing anything to get his wealth: he doesn't plant, he doesn't distribute (diaskorpízō) his wealth. He just collects interest on it from the misery of people who were sucked into the downwardly spiraling system.
So he denounces the crime, buries the money, and in the end gets crucified for his actions. It is telling that he put the money in the ground, which is ultimately owned by God (Leviticus 25:23-28). Is Jesus saying that he gave the money back to God, the ultimate owner? The ground is also where Judas hid his "blood money" when he realized that it had just caused his friend's death.
So, what are the preaching themes and possibilities in this story? There are two traditional readings of this story. The first is that the (evil, greedy, wicked) Master is Jesus, who left us for a while and will come again at the end of time for an ominous reckoning of how we have used or misused our "talents" (usually mis-interpreted as skills and gifts). That's an odd role for Jesus, but it seems to have survived thousands of years of puzzled looks during children's sermons. A second traditional reading is that God is the (evil, greedy, wicked) Master who does the judging, and who is just as nasty in the end. Making God the "heavy" somehow doesn't feel any better than making it Jesus, but there you are. The way that my pastors as a child got around this was to ignore that the third servant got tossed into outer darkness, and gave heroic examples of the non-squandering of our "talents."
Perhaps, instead, this is not an allegory. Perhaps Jesus was simply saying that if you stand up and denounce an immoral, evil, system, you may have to pay for it. Perhaps Jesus was saying that sometimes--like Shadrach, Meshach, and Abednego in the fiery furnace (Daniel 1-3)--the right thing to do is to offer up your life as a bulwark against injustice, even if it means losing that life.
Perhaps the message of the story is simply that the story is true, and that if you don't like it, what are you going to do about it?
 The Wars of The Jews, Flavius Josephus, tr. William Whiston Book 2, Chapter 17, par. 6 (http://www.gutenberg.org/files/2850/2850-h/2850-h.htm#link22HCH0017).
 Bruce J. Malina and Richard L. Rohrbaugh, Social Science Commentary on the Synoptic Gospels (Minneapolis: Fortress, 1999), p. 149.
 William Herzog, "The Vulnerability of the Whistleblower," Parables as Subversive Speech: Jesus as Pedagogue of the Oppressed (Westminster/John Knox: 1994), p.157-8.