Many of my clients breathe a sigh of relief when they learn that a prosecutor has offered a plea deal that is likely to result in much less incarceration time than through a trial loss, when they believe that the risks of a trial loss are high.

When discussing the options between going to trial, accepting a plea offer, or returning with a counteroffer, I focus my clients on the bigger picture than their likely latest jail or prison release date. I remind them that they also face a probation length and probation conditions upon release that can be both unpleasant, and lead to more incarceration in the event of a probation violation finding. I focus them on the numerous adverse collateral consequences of convictions, including on employment, reputation, immigration in the United States and abroad, and other possible collateral consequences. I advise them that each new conviction will become a bigger problem with all future criminal prosecutions, including pretrial release and sentencing.

Sometimes I need to have this same conversation — or an abbreviated form of the conversation — several times with my clients before they are able to use the information to make an informed decision.

Then, the Supreme Court and other appellate courts underline the importance of such conversations with my clients, including today’s Supreme Court case that reminds us not only of the harsh reality of repeat offender laws, but underlines that one of the federal repeat offender sentencing laws — the Armed Career Criminal Act — looks at the state of the law at time of each conviction for determining whether a prior offense was a serious drug offense triggering a harsher sentence, regardless of any subsequent softening of the law that led to the prior conviction. McNeill v. U.S. ___ U.S. ___ (June 6, 2011).

Do not let the caring- or intelligent-looking gaze of a trial or appellate judge lull anybody into a false sense of a lenient sentence. Judges will not permit a sentence any more lenient than they believe the sentencing laws permit.