After pleading guilty to a crack cocaine crime, a Providence man received three different prison sentences — ranging from about 13 1/2 years to about 19 1/2 years.

And he was seeking a fourth, lower sentence when an appeals court this month said he’d have to settle for 15 years in a federal penitentiary.

Antron Russell’s roller-coaster sentencing ride highlights a series of major rulings regarding the freedom judges now have to vary from federal sentencing guidelines and to consider the disparity in the way the guidelines treat crack versus powder cocaine.

The case also provided the Boston-based 1st U.S. Circuit Court of Appeals with a chance to declare that it had actually been ahead of the curve — and not at odds with — a 2007 Supreme Court ruling that says sentencing judges may take into account the crack/powder disparity on a case-by-case basis.

Russell’s case focuses on sentencing guidelines that, until recently, treated 100 grams of powder cocaine as the equivalent of 1 gram of crack. That 100-to-1 ratio did not mean crack sentences were 100 times longer than those for powder. (The ratio resulted in sentences three to six times longer for crack.) But it did mean that selling 50 grams of crack triggered a mandatory minimum sentence of 10 years, while it took 5,000 grams of powder cocaine to trigger that same sentence.

Debate about the disparity has raged since the 1980s when Congress passed the Anti-Drug Abuse Act, saying crack was more addictive than powder cocaine, more often linked to other serious crimes and more likely to be used by “vulnerable members of society.”

Critics have challenged those assumptions and called the disparity racist, noting its disproportionate impact on black offenders such as Russell. Critics also have said the disparity resulted in harsher penalties for small-time crack dealers rather than kingpins bringing powder cocaine into the country.

In a statement issued Friday, U.S. Attorney Robert Clark Corrente said, “The recent decisions by the U.S. Supreme Court have afforded trial judges greater discretion in sentencing matters. However, we believe that a case like Russell highlights the importance of tough federal sentences. A defendant like Mr. Russell, who is undeterred by three prior prison terms, who repeatedly sells large quantities of crack, and who recklessly endangers both police officers and bystanders in a violent escape attempt, richly deserves the [15-year] sentence that the court imposed.”

Edward C. Roy Jr., supervising assistant federal defender in Rhode Island, said Russell’s fluctuating sentences show “there is a range of reasonableness.”

Roy, who represented Russell, said he was disappointed that the 1st Circuit upheld the 15-year sentence, but he said federal defenders plan to seek a reduction in Russell’s sentence based on U.S. Sentencing Commission action that has narrowed the crack/powder disparity.

Russell, 27, formerly of 60 Comstock Ave., Providence, remains at the U.S. Penitentiary in Lewisburg, Pa., according to the Bureau of Prisons Web site.

His case stems from March 2003, when the police learned that a man fitting Russell’s description was planning to sell crack at a McDonald’s restaurant in Cranston. According to the decision, Russell arrived at the McDonald’s parking lot in a car driven by a woman. Police officers approached both sides of the car and removed the woman. Russell reached over and drove the car back and forth, hitting three officers as he tried to escape. The police opened fire at the car to stop it. He was not hurt.

Russell was found with 141 grams of crack cocaine in his pocket, and he later admitted to selling another 92.5 grams of crack to undercover officers on three prior occasions, according to the decision.

As part of a plea bargain, Russell pleaded guilty to possession with intent to distribute more than 50 grams of crack. In August 2004, U.S. District Judge William E. Smith imposed a sentence of 19 years and 7 months, which was at the low end of a mandatory sentencing guidelines range.

Russell appealed. And in January 2005, while the appeal was pending, the Supreme Court issued a ruling in the case of United States v. Booker, saying sentencing guidelines were merely advisory and no longer mandatory. Prosecutors agreed that resentencing was required.

At the second sentencing hearing, Russell’s lawyer sought the mandatory minimum sentence of 10 years, saying a shorter sentence would aid Russell’s rehabilitation. The defense also argued that Russell’s criminal history had been overstated and that the 100-to-1 powder/crack ratio was unjust, according to the decision.

But federal prosecutors asked the judge to reimpose the sentence of 19 years and 7 months, saying Russell had a long list of adult arrests and convictions and that three short prison sentences had not deterred him. Prosecutors argued that “it should be left to Congress, not the courts, to modify or even abrogate in its entirety the sentencing distinctions between crack cocaine and powder cocaine,” and they said that if different judges use different ratios to calculate crack sentences, “substantial sentencing disparities would arise,” according to the decision.

Smith categorically disagreed with the 100-to-1 powder-to-crack ratio in the sentencing guidelines, saying a 20-to-1 ratio should be used. The judge then imposed a sentence of 12 years and 7 months — seven years less than the previous sentence.

Still not satisfied, Russell appealed. Prosecutors cross-appealed, arguing that Smith’s categorical rejection of the 100-to-1 ratio violated a ruling that the 1st Circuit issued in January 2006 in another Rhode Island case.

In United States v. Pho, the 1st Circuit said then-Chief U.S. District Judge Ernest C. Torres had been wrong to substitute a 20-to-1 ratio for the 100-to-1 ratio in sentencing a pair of crack offenders. The Pho case, decided two months after Russell’s second sentencing, marked the first time a federal appeals court had weighed in on whether a judge could categorically reject the 100-to-1 ratio under advisory guidelines.

In light of the Pho ruling, the 1st Circuit kicked Russell’s case back to Providence, where Smith imposed the 15-year sentence. Smith explained that he had “undervalued” several factors at the previous sentencing — including the large amount of crack involved and Russell’s violent escape attempt. Smith noted the car hit three officers, officers fired their guns, and “this all occurred at a McDonald’s restaurant, a busy place. There could have been children running around.”

Russell appealed again, seeking support from the Supreme Court’s 2007 ruling in Kimbrough v. United States, which said judges may consider the crack/powder disparity in deciding whether a sentence within a guidelines range is greater than necessary.

But the 1st Circuit rejected Russell’s appeal this month, saying he would not be able to parlay the Kimbrough decision into a fourth sentence.

The 1st Circuit said its decision in the Pho case has been widely misunderstood, and it questioned why the Supreme Court had overturned Pho when it decided Kimbrough. The Pho decision did say that judges could not categorically substitute one crack/powder ratio for another based on “general disagreement with broad-based policies.” But the 1st Circuit emphasized that the decision also said judges could consider the “nature of the contraband and/or the severity of a projected guideline sentence” on a case-by-case basis.

“This case-by-case individualized analysis is precisely the approach endorsed by the Supreme Court in Kimbrough,” 1st Circuit Judge Kermit V. Lipez wrote. “Thus, at its core, Pho is actually consistent with Kimbrough: both decisions emphasize the importance of individualized, case-by-case sentencing determinations, rather than a reliance on generalized ratios.”

At Russell’s third sentencing hearing, Smith undertook the proper analysis in weighing the crack/powder disparity and other case-specific factors, the 1st Circuit said. At that hearing, Smith said the Pho decision called for judges to avoid basing sentences on “across-the-board” policies and to fashion sentences “on a case-by-case basis.” The 1st Circuit said that view of Pho was “consistent with the Supreme Court’s later holding in Kimbrough,” and it said Smith “presciently anticipated the guidance that the [Supreme Court] would provide in Kimbrough.”

The 1st Circuit took note of the challenges posed by the Supreme court ruling that said guidelines are no longer mandatory. “This case crystallizes the difficulties confronted by defendants — and district court judges — as they navigate the turbulent waters of Booker and its aftermath.”

The winding legal path of Antron Russell:

August 2004: U.S. District Judge William E. Smith sentences Providence’s Antron Russell to 19 years and 7 months in federal prison for possession with intent to distribute crack cocaine.

January 2005: U.S. Supreme Court issues ruling in United States v. Booker, saying federal sentencing guidelines are no longer mandatory. In light of the Booker ruling, the 1st U.S. Circuit Court of Appeals sends Russell case back to U.S. District Court in Providence for resentencing.

October 2005: Judge Smith sentences Russell to 12 years and 7 months in prison, stating a categorical disagreement with sentencing guidelines that then treated 100 grams of powder cocaine like 1 gram of crack.

January 2006: The 1st Circuit issues ruling United States v. Pho, saying judges can’t base sentences on categorical disagreements with broad policies but can consider, on a case-by-case basis, the type of drug and the severity of a projected guideline sentence. In light of the Pho ruling, the 1st Circuit sends Russell back to Providence for resentencing.

May 2007: Judge Smith sentences Russell to 15 years in prison, saying he’d previously “undervalued” factors such as Russell’s violent escape attempt.

August 2008: 1st Circuit upholds Russell’s 15-year sentence.

efitzpat@projo.com