Robert Freeman did some insider trading. John Poindexter deceived Congress. Fred Hagler helped another guy sell 2.3 ounces of crack.

They have two things in common: None deserves to go to prison. Yet all probably should-for a few months-to deter others from doing what they did.

But that’s not quite the way it’s going to turn out. And the differing prospects of these three men shed an unflattering light on our system of justice and our society’s moral sense of proportion.

Freeman, former head of arbitrage at Goldman, Sachs & Co., was sentenced April 17 to four months (plus a $1 million fine) for seeking inside information about a pending takeover and using it to unload $500,000 in options.

Poindexter, convicted April 7 on five felony counts of false statements to Congress and obstruction of its investigations into the Iran-Contra affair, faces a theoretical maximum of 25 years.

But he will probably get two years or less-and maybe no prison time at all, like his co-conspirators Robert McFarlane and Oliver North.

Fred Hagler acted as middleman between a small-time drug dealer and buyers (who turned out to be undercover operatives), and attended the sale. He was sentenced in April to 20 years, without parole.

A 37-year-old father of three, he will be locked up until at least 2007, and that’s if he earns all possible good-time credits. But for an unusual break he received from the prosecution, Hagler would have faced a congressionally mandated minimum prison term of life without parole.

Courtroom of the Absurd

This for a doer of odd jobs who eked out a meager existence with his common-law wife and children in a Los Angeles ghetto, a man who was wiretapped asking a customer for a $60 loan so he could go "down to Toys-R-Us" to buy his little boy a birthday present.

Convicted of helping sell the 2.3 ounces for $1,350, Hagler fell under a mandatory minimum of 10 years without parole for selling more man 50 grams (1.8 ounces) of crack. The term is "enhanced" to 20 years if the defendant has one prior drug felony conviction, no matter how petty, and to life without parole if he has two.

Hagler got 20 years instead of life because federal prosecutors in Los Angeles recognized the absurdity of giving him a stiffer sentence than most murderers and asked the judge to disregard one of his two minor prior convictions for cocaine possession.

The prosecutors demonstrated more sense than Congress, which gave judges no discretion at all to go below the statutory minimum sentence.

If 20 years is lenient for a Hagler, what about a Freeman or a Poindexter, whose crimes were far greater?

In fact, it would be pointless cruelty to send Freeman to prison if the only question were what punishment he deserved, in the retributive sense. Publicly humiliated and professionally ruined, he poses no danger to society. U.S. District Judge Pierre Leval, noting that insider trading had become a "standard practice of arbitrage," found Freeman "chastened" and basically decent.

But the judge said jail time was needed to deter the many others on Wall Street who "think themselves authorized to disregard the law."

A case like Freeman’s is hard because the goals of retribution and deterrence point in opposite directions.

How Low to Stoop

When a defendant’s actions typify the ethical standards of his community or profession, the case for retribution diminishes. We cannot fairly attach great culpability to the failure to be more ethical than one’s peers. But the more corrupt the ethical standards of the defendant’s peers, the greater the need to make an example of him.

How big a piece should we take out of one person’s life to teach others a lesson? Not very big. Judge Leval’s four months seems about right.

Similar logic applies to Poindexter. His crimes were serious, but motivated by a sincere, if misguided, sense of duty. His career was exemplary, from the time he led his class at the Naval Academy until he became Ronald Reagan’s national security adviser.

The president wanted him to do things that could not be done without deceiving Congress and the public, which the president and lots of his other aides did too. It would be unfair to imprison the dutiful Poindexter alone for the Iran-Contra lies while Reagan sits in California and North grandstands around the country.

But executive-branch officials need it kicked into their heads that they do not have a license to lie. Six months would be a reasonable compromise.

Fred Hagler seems at first a different story. Wall Street Journaleditorialists and others who see Freeman and Poindexter as persecution victims shed no tears for Hagler’s ilk. It’s hard for most of us to identify with a drag dealer.

But most of us were not orphaned as children, as was Hagler by his mother’s death and his father’s desertion. Most of us did not grow up in foster homes and drop out of high school. Most of us have not had to scratch out a living on the streets of South Central Los Angeles, where the drug culture is pervasive and where Hagler had to dodge dealers to take his daughter out for ice cream.

By the standards of his community, Hagler’s criminal record is unimposing: in 37 years, a $65 fine for battery, a $50 fine for disturbing the peace, a suspended one-year sentence for having a small amount of cocaine in 1983, and 90 days in jail for a similar charge in 1984. And now the 2.3-ounce crack conviction, which he is appealing.

No killings. No rapes. No robberies. No burglaries. No thefts. No weapons. No large quantities of drugs.

The worst thing he did, if he did it, was to sell small amounts of drugs to eager buyers who would have bought them elsewhere if not through him.

Like Freeman and Poindexter, Hagler joined in the criminality that surrounded him. His crime was as representative of the moral standards of his community as was Freeman’s.

Despite the demonization of drag dealers that led to the insane sentences now on the books, Hagler may be the least culpable of the three: He was a struggling small-timer; Freeman and Poindexter were highly placed enough to set ethical standards for others.

The retributive justification for giving Hagler any prison time at all is weak. Deterrence probably does call for giving people like him a few months, so others will know they cannot flout drug laws with impunity. But 20 years without parole is obscene.

The prosecution said the sentence was justified because "drug dealers are destroying that community."

Hogwash. Hagler’s contribution to the destruction of his community ranks with a cigarette-selling pharmacist’s contribution to the 300,000 deaths a year caused by smoking.

Nor is there much deterrent value to draconian prison terms for small-time drug defendants. To the contrary, since they were adopted in 1986 and 1988, the supply of drugs has increased.

A glimpse of what these laws have done came at the sentencing of Fred Hagler and Ms co-defendant, 20-year-old Stephen Green, who received the 10-year mandatory minimum.

Green’s mother, in the back row, began wailing for mercy for both men. Henry Weinstein of The Los Angeles Times reported the scene:

"Please! Please!" begged Mrs. Green, a mother of eight with a $3.75-an-hour job at a convalescent home. "Fred is a good man. He works on cars. We’re poor black people. This is a terrible neighborhood."

Judge Alex Kozinski of the U.S. Court of Appeals for the 9th Circuit, sitting specially as a district judge, told her gently that "this is extremely painful" but Congress had given him no choice.

"Stephen is young," the judge said. "He’ll survive this."

"No, he won’t," yelled Mrs. Green’s daughter, Dietra. Then she led her weeping mother away.