For Michael Milken, hailed as one of history's most brilliant financiers, the 10-year prison sentence he received Wednesday surely was the worst payoff he ever obtained on any deal.

The startlingly stiff sentence dashed Milken's hopes for a relatively short jail term in return for his agreement to plead guilty to six felonies last April.

As a result, the sentence has raised questions about the legal defense strategy pursued by Milken and his attorneys, led by star New York litigator Arthur L. Liman. With the benefit of hindsight, some legal experts say the Milken team erred in fighting the government for more than three years before finally throwing in the towel seven months ago with the plea bargain.

In the process, Milken spent more than $50 million in legal fees and dragged himself and his family through a contentious and highly publicized battle with the government, only to receive the toughest sentence ever for securities crimes. The sentence was tacked on to the $600 million penalty he agreed to pay in his plea agreement.

The sentence was "a fitting conclusion to ... years of denial and obstructing the government's investigation," said attorney Harvey Pitt of the District law firm Fried, Frank, Harris, Shriver & Jacobson who advised Ivan Boesky on his 1986 plea bargain. Boesky agreed to cooperate with the government by fingering Milken and others and ended up with what was viewed as a light, three-year prison term for his single guilty plea.

"I think {the sentence} proved that his strategy was defective," Pitt said about Milken.

Sources said that Milken's defense team, while recognizing that the result was disastrous, believes that it was impossible to predict that U.S. District Judge Kimba Wood would penalize Milken so severely. The punishment was more than double the longest prison term -- four years -- previously meted out in the wave of Wall Street criminal cases that began in 1986.

According to the most frequently voiced criticism of Milken's defense strategy, the financier and his lawyers would have done better to cut a deal much earlier than they did, and thus obtain credit for not forcing the government to pay the price in effort and money to prosecute him.

Pitt was among several veteran securities defense lawyers who said that if Milken had agreed to cooperate fully with government investigators when he pleaded guilty last April, that almost certainly would have mitigated the harshness of his sentence.

"I think {Milken and his lawyers} thought if he didn't cooperate, and therefore didn't reveal the true extent of all of his misdeeds, that he would get a lighter sentence," Pitt said.

"The strategy that they pursued was tough it out, denial, make the government work for every inch it gets. The problem is that in the meantime, everything corroded around him. ... This thing went on too long. If you are going to cut a deal, you want to cut it early before the government gets rolling and before people turn against you," Pitt said.

In sentencing Milken, Wood said she could not reward him now for any help that he may give the government in the future in tracking down other business felons. Instead, she merely held out the possibility that his sentence might be reduced if he provides so much assistance that the government returns to court and requests a shorter jail term.

Michael Armstrong, the attorney who represented Milken's brother Lowell, argued that it was unfair to criticize the defense strategy because the 10-year sentence was an aberration.

"It is so out of line that there is no way a responsible lawyer could have anticipated this sentence," Armstrong said in a telephone interview in which he emphasized he was offering his personal opinion. "You count on the fact that there is some reward for pleading guilty, and again, when you put together the factors -- white-collar first offense with a {guilty} plea and a favorable probation report -- the idea that you would get a 10-year sentence is crazy."

He added: "One thing is for darn sure -- nobody is ever going to plead guilty before Kimba Wood again."

Michael Milken's lead defender, Liman, who previously was in the public spotlight as the chief Senate counsel in the Iran-contra hearings, declined to comment. But a source close to the defense team led by Liman said nobody ever advised Milken that he might receive a 10-year sentence.

"That's because all advice was based on the expectation that sentencing would be predictable and consistent. This was neither predictable nor consistent," the source said.

Nevertheless, there were several indications that the Milken strategy had gone awry. For instance, Wood said that she penalized Milken harshly because, among other reasons, she felt that he had obstructed justice by encouraging his colleagues at Drexel Burnham Lambert Inc. not to cooperate with the government probe.

It seems that Liman made a mistake in arguing vociferously, even after Milken cut the plea bargain, that his client did not obstruct justice and that he had pleaded guilty only to largely technical violations, lawyers said.

"In the whole, if you look at it, it is a series of halfway steps toward cooperation," said attorney Robert McCaw, a partner with the D.C. law firm of Wilmer, Cutler & Pickering who represented Boesky. "To fight for a long time and then cut a deal, and even in that deal not to acknowledge that you {obstructed justice}, was to have the worst of all possible worlds," McCaw said. "You don't get any credit for cooperation, and you get substantial detriment for your obstruction."

McCaw joined other observers in noting that the defense's key argument -- that Milken's crimes were rare and relatively minor regulatory offenses -- was thrown back at Milken by the judge.

"The other thing clear in the courtroom {on Wednesday} was that the strategy of saying these were isolated technical crimes backfired," McCaw said. "The {presentencing} hearings convinced the judge they were not isolated or technical crimes and deprived Milken of the credit that you get for genuine remorse."

Milken did obtain some important benefits from the plea bargain. He got immunity from criminal prosecution for Lowell Milken, also a former Drexel executive who had been charged with various financial market crimes. And by refusing to lead prosecutors to other suspected Wall Street criminals, Milken avoided the stigma attached to Boesky of being a "squealer."

Moreover, many lawyers said it was unfair to play "Monday-morning quarterback" without knowing details of the interplay between Milken and his attorneys. "It is wrong to second-guess the lawyers' strategy," said Ted Levine, a partner at Wilmer Cutler. "Ultimately, it is the client's decision. You don't know what a lawyer recommends. You only know what he implements. It is easy to look back and say it was the wrong judgment now. I don't think it is fair."

There is little question that the key legal strategy decisions, including the decision to fight the government for so long, were made by Milken. But, according to some sources, there were differences at times in the counsel Milken received from Liman and other attorneys at the New York office of the law firm Paul, Weiss, Rifkind, Wharton & Garrison and the advice he got from the Washington law firm of Williams & Connolly.

The Paul, Weiss attorneys were inclined to fight while Williams & Connolly attorneys were inclined in early 1989 to settle the case in the hope that Milken might receive a lesser sentence.

Milken hired both law firms to represent him once his legal troubles began in 1986. While Liman led the defense for Paul, Weiss, Milken's original counsel at Williams & Connolly was noted defense attorney Edward Bennett Williams. But as Williams's health deteriorated prior to his death in 1988, Williams & Connolly partner Vince Fuller took a leading role.

In early 1989, sources said, Fuller, along with his partner Robert Litt, entered into negotiations with government prosecutors that nearly led to guilty pleas by Milken to two criminal counts, a more lenient deal than the one he ended up with earlier this year.

There was never a face-off between attorneys from the two law firms, and some sources disputed that there was even a difference of approach. But other sources said it was clear at the time that the attorneys at Williams & Connolly generally favored settling, while Liman and his partner Martin Flumenbaum at Paul, Weiss favored fighting.

In the end, as Milken received somewhat conflicting opinions, the deal fell apart.