Mr. Moncrieffe is originally from Jamaica, but has legally lived here in the U.S. for many years. His lawyers faced the same dilemma we face when representing aliens accused of crimes, the question of whether a guilty plea might make the person subject to deportation (or “removal” as the term is now called). Like many people, Mr. Moncrieffe seemed ready to accept a deal that called for no jail time and expungement. Little did he know that the feds wanted to kick him out of the country for this relatively minor offense.

Under the immigration laws, a drug distribution crime falls into the category of “aggravated felonies”. These more serious crimes make it almost impossible for an alien to avoid removal once the immigration authorities start their machinery in that direction. Pursuant to the immigration laws, a noncitizen convicted of an “aggravated felony” is not only deportable, but also is not eligible for discretionary relief. Under the immigration laws, an “aggravated felony” includes anything that is the “illicit trafficking in a controlled substance.” To understand yesterday’s ruling, it is also important to realize that pursuant to the federal drug laws, marijuana distribution is a felony, but if it only involves “small amounts” that are distributed for no remuneration, then the offense is merely a misdemeanor.

The emerging star of this Supreme Court Term, Justice Sonia Sotomayor, wrote for the majority in the 7-2 opinion. Justice Sotomayor noted that under Georgia law, marijuana distribution encompasses a range of conduct from social sharing to distribution of larger amounts. She also noted an issue that has regularly bedeviled the federal courts: how to categorize a person’s prior offenses. Over the recent decade, the Court seems to be inclined to use something called the “categorical” approach. Under this analysis, courts examine what the state conviction necessarily involved and not the facts underlying the case. In using this approach, the federal court assessing the impact of a prior conviction presumes that the conviction rested upon nothing more than the least of the acts criminalized. After using this “least serious version of the crime” approach, a judge is then supposed to determine whether even those acts are encompassed by the generic federal offense that is similar to the state crime at issue.

Justice Sotomayor then turned to how drug offenses are analyzed to see if they fall into the “aggravated felony” pigeonhole. She said that a state drug offense must meet two conditions: it must proscribe conduct that is an offense under the federal drug laws, and the federal drug laws must “necessarily” prescribe felony punishment for that conduct. Although possession of marijuana with intent to distribute is clearly a federal crime, as noted above it turns into a misdemeanor when it involves only a small amount distributed for no remuneration. The Georgia drug distribution statute includes people (like Mr. Moncrieffe here) who had small amounts of pot with no desire to be paid for sharing their stash. Using the categorical approach, federal courts must assume the least serious version of the crime, and therefore violation of this statute cannot be the “aggravated felony” that causes almost automatic deportation.

Again, this kind of case reveals the difficulty in defending clients who are not citizens. It also shows the problem in dealing with seemingly minor drug cases. People need to be careful when hiring lawyers for such matters, to make sure their attorney is up on the law and possible consequences of a conviction.

In 2010, the U.S. Supreme Court recognized this deficiency in Padilla v. Kentucky, 559 U.S. ____ (2010), when it ruled that 6th Amendment protections require criminal defense attorneys to inform non-citizen clients when there is a risk of deportation as a result of a guilty plea. After Padilla, non-citizens who were placed in removal proceedings for their criminal conviction were able to raise specific 6th Amendment challenges through petitions for habeas corpus and other similar post conviction mechanisms.

What happens if a person’s conviction occurred prior to the Padilla decision in 2010? The District Courts were left to determine the answer, and many reached different results using the “new rule” principles of Teague v. Lane, 489 U.S. 288 (1989). Essentially, if the Court announced a “new rule” in Padilla, the holding cannot apply to subsequent challenges with already-final convictions. However, if the decision was merely an application of the existing standards that govern ineffective assistance of counsel established by Strickland v. Washington, 466 U.S. 668 (1984), then the ruling could be applied retroactively to convictions entered prior to 2010.

In the recent Chaidez case, the Supreme Court said that the Padilla rule does not apply retroactively. Here’s how they got there. First, instead of simply assessing whether Padilla’s representation fell “below an objective standard of reasonableness,” which is the “regular” Strickland test, the Supreme Court for the first time said in Padilla that an attorney must affirmatively advise a client of the negative collateral consequences of a guilty plea. Next, the Court noted that the main question in Padilla was not whether counsel was ineffective by remaining silent on the issue, but rather “does the scope of the 6th Amendment extend to consequences outside of the criminal proceedings?” Because there was no prior precedent which dictated this answer, the Padilla decision “broke new ground.” Because it broke new ground, the rule is not applied retroactively to cases handled before the Padilla decision was announced.

Unfortunately for Ms. Chaidez and many others, when an immigration attorney completely fails to advise that an aggravated felony conviction triggers mandatory deportation, this failure by the lawyer cannot be challenged under Padilla if the plea was entered before 2010. However, all may not be lost because the Court hints at the remaining potential for challenges under the pre-existing Strickland test. It leaves open the possibility to challenge “material representations” where the client is affirmatively misled with the wrong advice regarding deportation or another collateral matter. Ultimately, the Court highlights that deportation “is a ‘particularly severe’ penalty,” and advice of a plea’s deportation risk should “not [be] exempt from Sixth Amendment scrutiny.”

Does this mean that non-citizens who pleaded guilty before March 31, 2010 should simply give up without attempting to challenge their lawyer’s ineffective assistance of counsel? Of course not. A person facing deportation from a country she considers home may feel it is worth every effort to fight removal, so long as it is understood that this recent decision limits the likelihood of success.

The case is United States v. Gustavo Dominguez. Mr. Dominguez is a naturalized U.S. citizen who was born in Cuba. Mr. Dominguez has represented numerous Cuban nationals who came to this country and later became professional baseball players. The government’s theory was that Dominguez conspired with others who smuggled the potential players into this country, with the goal of later representing the players if and when they were snapped up by a Major League franchise. The players were taken to California where Dominguez got an experienced immigration attorney to help them work through the immigration process. The trip to California and the immigration applications led to charges of transporting illegal aliens and concealing or harboring them in this country.

The jury found Mr. Dominguez guilty of conspiring with and aiding others who smuggled the players into the country. Additionally, the jury held that Dominguez was guilty of helping to transport the Cuban players from Florida to California and also found him guilty of harboring or concealing these same players. The majority of the Court of Appeals Panel reversed the convictions relating to transporting and concealing the players. Basically, the majority held that by taking the players to an attorney Dominguez could not be guilty. Oddly, the majority affirmed the convictions for smuggling these same players.

Judge Tjoflat wrote a spirited dissent. He explained that the trial court’s rulings basically required that someone in Mr. Dominguez’s situation needed the sophistication of a “Philadelphia lawyer” in order to wade through issues related to people who enter this country from Cuba, related to the “wet foot-dry foot” policies that apply solely to immigrants from this one country. According to Judge Tjoflat, Dominguez should receive a new trial where he can present testimony concerning this policy and his state of mind.

We represent several employers either charged or threatened with indictment for employing persons from other countries who turn out to be here illegally. This case is just the most recent illustration of how federal immigration policy often intersects with the law involving defending a person against a federal criminal prosecution.