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After Jesus exhorts the disciples to "keep watch," to stay awake, he illustrates what he means. We stay alert not by artificially and perpetually stirring expectation that he will come at a given time, but by living in such a manner that we would have no cause for shame if he did come at any time, since he may in fact do so. Paul may echo the warning against living an unexpectant, self-serving life here (compare 1 Thess 5:3-9).
Of the one to whom much is given, much is required. Ministers have special responsibilities to serve others (Lk 12:41-42; compare Hos 4:6-9; 1 Pet 5:1-4). This parable shows that Jesus' assault on hypocritical leaders in Israel (Mt 23) is also applicable to those in the church at the Second Coming who prove equally unprepared (compare 25:14-30; Jas 3:1; see Meier 1980:293-94; Gundry 1982:497). Here the ruling servant exploits the resources meant for others through his gluttony and drunkenness (Mt 24:49; compare the demand for sobriety in Lk 21:34; 1 Thess 5:6-7). "You have ruled [my sheep] harshly and brutally" (Ezek 34:4).
Some servants of Christ will be as unprepared at his Second Coming as was much of the religious establishment at his first. Sharing hell with the hypocrites (Mt 24:51) explicitly recalls the false servants of 23:13-29. Like the tenants of 21:35-37 or the shepherds failing to feed the sheep in Ezekiel 34:15 (compare Mt 24:45), these leaders forgot their true role as servants (23:12) and acted as if they could do as they pleased with those God had entrusted to their care.
Ministers who exploit the flock for their own interests will be damned. See also 2 Peter 2:3. Jesus is severe on leaders who are responsible for crushing or misleading others, not because he does not love these leaders but because he also loves the people they are exploiting. Jesus calls us ministers to serve our fellow servants, and we do ourselves a disservice by toning down Jesus' willfully strong language about the lostness of those who do not. If we are (for example) more concerned about getting a good "altar call" for our own self-esteem than about building up the flock with sound teaching or sharing Christ beyond the church's walls, we are using church members for our own interests. Ministers who use churches merely as stepping stones for personal ambition or who are more interested in preserving their wages than fulfilling their calling (see Mic 3:11-12; 1 Tim 6:5) could discover on the day of judgment that they will not spend eternity with the Lord they proclaimed.