In the modern understanding of the word, “sophistry” has a decisively negative connotation. It refers to people who envelop, even purposely trick and deceive you with words. Nonetheless, the original sophists were a group of wandering philosophers; they would charge money for sharing their knowledge and were known for their reasoning skills as well as their manners of persuasion.
The ancient Greek sophists, and often Socrates is mixed up with them, were said to be “corrupters of youth” as their teachings often clashed with the conservative and age-old traditions of the Greek forefathers. By providing youth with a different definition of truth - away from the mindless following of rules and a more sharpened awareness of one's own impact on the world – these philosophers must have caused resentment in a society that preferred the already established morals and values.
In this case, one should, however, point out that Socrates (and his pupil Plato shared this view) did not necessarily like the sophists, not so much because of their teaching, but for the fact that they had the audacity to ask for money for something that everybody is said to already possess. Socrates compared himself to the midwife who brings out the truth in each individual, and he considered it rather immoral to ask anything in return for his work as a truth-seeking philosopher.
However, there are more problems arising from this situation. It is, to put it in modern jargon, making commerce of a profession that ought to be kept pure from monetary influences. If money is allowed to enter the philosophical realm, then the quest for wisdom becomes tarnished.
Why? Because others might be prone to use flattery for profit and popular esteem. When the person is given the truth he or she “wants” to hear, they would be more willing to pay; yet when you tell them unpleasant facts about themselves, your profit margin would tend to decrease.
Compare it to a visit to the local psychic. People who go there have a predominant question on their minds, and they want to hear a certain truth or reassurance to come out the mouth of the psychic to collaborate their own initial beliefs to begin with. The psychic would be tempted to supply this preconceived “truth” so that the client remains satisfied and comes back for more, regardless of the validity of the statements.
Not to say that all sophists - or even psychics - behave in such a manner, but in a world where money and popular opinion rule, flattery becomes salient. A good example for this would be the modern obsession with media. Media has become another form of entertainment by feeding people more often than not what they want to hear. The media becomes rather focused on making profit instead of providing objective facts.
The actual truth about the matter will be on the back-burner when it comes to what actually sells; the media often falls into the trap of adjusting or tailoring to people's needs, fears and tastes, thereby becoming empty of value and truth.
This “commercialization” has unfortunately managed to spill even into areas such as art and literature. Many artists find it hard to resist the temptation or rather trap of “pleasing the crowds.” They would become less of an aggressor and critic of social customs and instead serve what people have been wanting to hear anyway.
This need for approval and for money is often so deeply ingrained that we, even as self-respecting artists, mostly do not realize on a conscious level how much we self-censor our own work to fit the paradigm that others consider art (even if we nobly deduct the financial aspect of it, we still want to “please” the ever-present critics). It is a pity, as the real unique voices that need to be expressed become muffled, mired or even drowned in commercial mud, and all we are left with is often a clever, yet meaningless and vacant sophistry of words and thoughts.