The phrase “Lawful Permanent Resident” is one of the more unfortunate expressions in our present immigration system. Residency under this status is about as “permanent” as the accompanying “green card” is green. There are now officially more ways to lose your residency than Paul Simon had to sneak out on his girlfriend, and many of them are not as obvious as you’d think. (Only in Immigrationland could first-degree murder and failure to report a change of address within ten days be legally equivalent.)

Perhaps even more unfortunate is the hypnotic effect that the word “permanent” can have on criminal lawyers when considering whether to recommend that a client enter a plea in a given case.  It is all too common for counsel in these situations to blithely state that the ensuing conviction won’t carry any immigration consequences without doing the research, or, as I recently heard an attorney argue in open court, that “permanent residents can’t be deported.” It’s easier just to assume the best, I guess.

So now comes Jose Padilla (not the dirty bomb guy), whose request for further review was accepted by the U.S. Supreme Court last month in what may prove to be one of 2009’s most interesting and impactful immigration-related appeals. Mr. Padilla was a lawful permanent resident of the U.S. for more than forty years after emigrating from Honduras, during which time he served in Vietnam and then took a job as a long-haul trucker. Unfortunately for him, his last load included over 1,000 pounds of marijuana, with which he was caught in Kentucky and indicted on misdemeanor (???!) possession and felony drug trafficking charges.

When considering his options prior to trial, Padilla’s attorney allegedly informed him that he shouldn’t be concerned with immigration consequences of any of this because he had “been in the country for so long.” Based on this advice, Padilla entered a plea and accepted a five-year prison sentence, after which he was immediately placed in immigration proceedings. His case has now reached the Supreme Court on the theory that his attorney’s advice as to the potential immigration consequences was Constitutionally ineffective.

This argument has been tried before in pretty much every jurisdiction, and it’s usually a loser. This is because immigration consequences are typically seen as “collateral” to a criminal conviction, just the same as when felons lose things like (in some states) the right to vote, or (historically, but not so much anymore) the opportunity to serve in the military. As such, criminal attorneys are not generally required to give actionable advice as to the potential immigration consequences of entering a plea in a given case. And this is pretty reasonable, on balance. State criminal law and federal immigration law intersect in the strangest ways and in the oddest places, and expecting the average criminal trial attorney to keep up with all of the crazy details and developments in this area might not be any more reasonable than expecting the average immigration lawyer to have a practical working knowledge of the countours of the hearsay rule and its many, many exceptions under statutory and common law.

But then again: if you are going out of your way as an attorney to affirmatively step up and offer advice to a client on any legal matter, you’d best come correct. Even in the most thoroughly bourbon-soaked backwoods of Appalachia, any reasonable criminal lawyer should know that Immigration might want to have a word with a non-citizen found to be freighting  a HALF-TON of quality Mexican Mary Jane in his motor vee-hickle. So I’ll go ahead and say it right here: “you’ve been in this country so long that they won’t care” was advice so errantly stupid, so eminently unreasonable, and so inarguably incompetent as to require the invention of a new legal standard several miles beyond “ineffective.”

And that is why Padilla is such an awesome test case. Basically, if the Supremes don’t find that this was ineffective assistance, they will likely never find that any immigration advice affirmatively provided to a client prior to a criminal plea ever could be. More as it happens…

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Like so many other great American ideas, the concept of court-ordered probation in lieu of committed time was born in Boston. In 1841, a local shoemaker named John Augustus volunteered to take a local drunk under his wing after paying the man’s bail in an effort to rehabilitate him through a proposed system which he called “probation.” After modest success in this direction, Augustus went on to counsel a total of 1,946 convicted criminals in a remarkable volunteer career which ultimately spanned more than two decades. Reflecting on a group of boys he took charge of in his early days as America’s first probation officer, he wrote:

…the scene formed a striking and highly pleasing contrast with their appearance when first arraigned. The judge expressed much pleasure as well as surprise at their appearance, and remarked that the object of the law had been accomplished, and expressed his cordial approval of my plan to save and reform.

The Commonwealth eventually agreed with this assessment, andMassachusetts became the first state to adopt a formal probation system in 1880. Even today, the courts of the Commonwealth now sentence defendants to probation more consistently than any other American state. (Or at least that’s what I heard on NPR the other day. I’ll try to source that a little better shortly.)

But just because we’ve been doing this longer than anyone else doesn’t mean that our probation system is perfect, as we we were reminded in today’s Appeals Court ruling in Commonwealth v. Gomes.

The defendant in Gomes was convicted of gun charges, with no allegations that he had ever had any issues with drugs and/or alcohol. Regardless of this, Gomes’s court-ordered conditions of probation specifically included not only a prohibition against drug and alcohol use, but also required him to be subjected to regular drug and alcohol screening throughout his eighteen months of supervised probation.

On appeal, the defendant acknowledged that the prohibition on drugs and alcohol use was reasonable (he was under 21 at the time), but argued that he shouldn’t have to pee in a cup on command for 18 months just because he had been caught with a gun.

The Appeals Court agreed and held for the defendant, noting that “[a] judge’s latitude in sentencing is great but not infinite.” Because drug and alcohol testing amounts to a Constitutional search and seizure, the Court found that such random testing may only be included as a condition of probation in cases in which this testing would be “reasonably related” to “recognized probationary goals” for a given defendant.

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