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					                       The Harlan Institute for Constitutional Studies

Josh Blackman |
Yaakov Roth |
January 5, 2010

                       Padilla v. Commonwealth of Kentucky
          Argued before the United States Supreme Court on October 13, 2009

Petitioner (Party Appealing the Case to the Supreme Court): Jose Padilla
Respondent: Commonwealth of Kentucky

Question: If an immigrant pleads guilty to a crime because his lawyer tells him that he
will not be deported as a result of pleading guilty, but the lawyer was wrong and the
Government attempts to deport the immigrant, can the immigrant withdraw his guilty

Case Background
Jose Padilla was born in Honduras and immigrated to the United States in the 1960s and
served in the U.S. Army. But he never became a full citizen. In 2001, he was arrested
for trafficking in marijuana and charged with various drug crimes in Kentucky court.
Padilla talked to his lawyer, who told him that if he accepted the prosecutor’s plea deal,
he would have to serve 5 years in prison but would not be deported from the country.
Padilla agreed to plead guilty. However, the lawyer had made a mistake of law, and in
fact once Padilla served his jail sentence, the Government would deport him to Honduras.

Padilla discovered the error a few years later, and brought a law suit to withdraw his
guilty plea and have a jury trial on his drug charges instead. Padilla claimed that his
lawyer was ineffective, thus violating Padilla’s Sixth Amendment right to effective
representation by an attorney.

Opinion of the State Supreme Court
The Kentucky Supreme Court did not agree with Padilla’s argument. The Court said that
because the Sixth Amendment only guarantees the right to a lawyer for criminal cases,
the fact that Padilla’s lawyer gave him bad immigration law advice does not matter. In
other words, the error made by the lawyer was on a “collateral” matter -- an issue only
indirectly related to the criminal charges that Padilla was facing -- and the Court decided
that guilty pleas could only be withdrawn if the attorney gave bad advice on a matter
directly related to the criminal case, like the length of the sentence or the chances that the
defendant would be found guilty.

Two Judges dissented (disagreed with the majority) on the Kentucky Supreme Court.
These Judges wrote that if the lawyer’s bad advice actually affects the defendant’s
decision to plead guilty or go to trial instead, then the lawyer is by definition not effective
and the defendant’s Sixth Amendment rights were violated. If so, the defendant must be
allowed to withdraw the guilty plea in order to cure the constitutional violation.

Padilla appealed this decision to the United States Supreme Court by requesting, or
petitioning for, a writ of certiorari, which the Court granted.

Argument of the Jose Padilla (Petitioner)
On appeal to the United States Supreme Court, Padilla argued that under the precedent of
Strickland v. Washington, 466 U.S. 668 (1984), a lawyer is constitutionally “ineffective”
if his representation of the defendant fell below the level of “reasonableness.” Some
clients, like Padilla, might care most about whether they get to stay in the United States
and not how long they must stay in jail, and so in such a case it would not be reasonable
for the lawyer to make a serious mistake about his immigration status. The distinction
between matters directly related to the criminal case, and those only indirectly related,
like future immigration consequences, is the wrong line: What should count is what
counts for the defendant in the particular case. According to Padilla, the Kentucky
Supreme Court’s approach is too mechanical and not realistic.

Argument of the Commonwealth of Kentucky (Respondent)
Kentucky argued that the Kentucky Supreme Court was correct. The lawyer’s duty is
only to tell the defendant what direct consequences he will face if he is convicted: for
example, how long he will be in jail, how big of a fine he will have to pay, and so on. He
cannot be responsible for also advising the defendant whether, if he pleads guilty, the
Government will deport him or he will lose his job or his wife will divorce him. That
would be impractical. And anyway, those are matters that fall outside of the criminal
process and the Sixth Amendment is not concerned with them. Because Padilla knew the
direct consequences of pleading guilty and decided to plead guilty anyway, he cannot
change his mind three years later.
                                 Constitutional Provision

Sixth Amendment to the United States Constitution
In all criminal prosecutions, the accused shall enjoy the right to a speedy and public trial,
by an impartial jury of the State and district where in the crime shall have been
committed, which district shall have been previously ascertained by law, and to be
informed of the nature and cause of the accusation; to be confronted with the witnesses
against him; to have compulsory process for obtaining witnesses in his favor, and to have
the Assistance of Counsel for his defence.
                                  Case Law Precedents

Strickland v. Washington, 466 U.S. 668 (1984).

In Strickland, the Supreme Court considered at what point a lawyer does so bad of a
job representing and defending a criminal defendant that the defendant has been
deprived of his right under the Sixth Amendment to the “Assistance of Counsel.” The
Court decided that the proper test is “reasonably effective assistance,” but what that
means depends on the facts of the case. There is no checklist because what is
reasonable depends on all of the circumstances. The main goals of the lawyer is to
make sure that the criminal process is fair, and courts must keep that in mind when
evaluating whether a lawyer was effective.

In the Court’s own words: “A number of practical considerations are important for the
application of the standards we have outlined. Most important, in adjudicating a claim
of actual ineffectiveness of counsel, a court should keep in mind that the principles
we have stated do not establish mechanical rules. Although those principles should
guide the process of decision, the ultimate focus of inquiry must be on the
fundamental fairness of the proceeding whose result is being challenged.”

Hill v. Lockhart, 474 U.S. 52 (1985).

In Hill, the Supreme Court considered the claim of a prisoner who said that his criminal
defense lawyer had been ineffective under the Sixth Amendment. The prisoner had pled
guilty to first-degree murder, but later argued that his lawyer had not advised him that he
would not be eligible for parole until he completed half of his jail sentence (35 years).
Instead, the lawyer had wrongly told him that he could be released on parole after
finishing only one-third of his sentence.

The Supreme Court refused to let the prisoner withdraw his “voluntary” guilty plea. The
Court applied the Strickland test described above, but did not decide whether erroneous
advice about a matter “collateral” to the criminal charge (that is, when the defendant
could get parole) failed the “reasonably effective representation” test. Instead, the Court
said that it did not matter because the defendant would probably have pled guilty anyway,
even if the lawyer had given him the right information about parole. After all, had he
gone to trial he might have received a longer sentence, and still would have been
ineligible for parole until finishing half of it.

[Note: assume for purposes of this exercise that Padilla would not have pleaded guilty
had he been told that he would be deported after serving his sentence.]
            Voting History of the Justices on Assistance of Counsel Cases

Wiggins v. Smith, 539 U.S. 510 (2003), involved a defendant whose lawyer did not
investigate the defendant’s childhood and background, or tell the jury that the defendant
had been severely abused as a child (so-called “mitigating” evidence). The jury
sentenced the defendant to death. The Court held that the lawyer’s performance was
ineffective, and ordered a new sentencing hearing with a new lawyer.

Schriro v. Landrigan, 550 U.S. ___ (2007), involved a defendant who told his lawyer not
to tell the jury about “mitigating” evidence, because he wanted the death penalty. The
lawyer complied and the defendant was sentenced to death. The Court held that the
lawyer’s performance was above the constitutional minimum.

Knowles v. Mirzayance, 556 U.S. ___ (2009): In this case, the lawyer advised the
defendant not to bring an “insanity” defense because it would probably lose. The
defendant agreed. Even though there was little cost to claiming insanity, it was not
ineffective for the lawyer to advise against it, because he made a reasonable judgment
that the jury would not believe the defense.

                   Wiggins v. Smith          Schriro v.              Knowles v.
                                             Landrigan              Mirzayance
Roberts             Not yet on Court              E                       E
Stevens                     I                      I                      E
Scalia                     E                      E                       E
Kennedy                     I                     E                       E
Thomas                     E                      E                       E
Ginsburg                    I                      I                      E
Breyer                      I                      I                      E
Alito               Not yet on Court              E                       E
Sotomayor           Not yet on Court       Not yet on Court        Not yet on Court

E = Lawyer’s performance was Effective under the Sixth Amendment
      I = Lawyer’s performance was Ineffective under the Sixth Amendment
                                     Teacher’s Guide

   Create a free account for your class at
   Join the “Harlan Institute for Constitutional Studies” at to compete against
    fellow classes across the Country participating.
   Assign 2-3 students to each of the Nine Justices, and ask them to explain how they
    think their Justice will decide the case. By analyzing the facts of the case, the relevant
    statutes, different precedents, and the voting history of the Justices, your students will
    need to determine whether their Justice will affirm, or reverse, the lower court.
   After your students make their predictions, add up the votes, and vote at Based on your students’ predictions, enter
    the Outcome (Affirm or Reverse), the Split (9-0, 8-1, 7-2, 6-3, 5-4, etc), and which
    Justices will vote with the Majority, and which Justices will vote with the Dissent.
   When the case is decided, see how your class ranks with other classes at

Issues to Discuss
 Discuss the hierarchy of state and federal courts. In this case, the Kentucky Supreme
    Court decision was reviewed by the United States Supreme Court, but only because it
    involved interpreting an Amendment to the federal Constitution. If the case only
    involved a question of Kentucky law (for example, the proper sentence for Padilla’s
    state drug crime) then the United States Supreme Court would have no power to
    review the Kentucky Supreme Court’s decision.
 This case presents a clash between bright-line rules and flexible standards. Should
    we have a clear rule that lawyer advice on “collateral” issues does not violate the
    Sixth Amendment? It would be easier to apply that rule. But flexible standards like
    the one articulated by the Supreme Court in Strickland -- that lawyers must stay
    above the level of “reasonably effective” -- allow courts to tailor the standard to all
    sorts of different cases and fact patterns. This is a tradeoff between fairness and
    predictability or efficiency.
 Consider discussing the gap between the constitutional text, which says only that
    defendants shall have the right to “Assistance of Counsel,” which might mean only
    that defendants can bring their own private lawyers, to our current understanding,
    which requires the Government to provide a free lawyer to the defendant, and allows
    the defendant to withdraw his plea or overturn his conviction if the lawyer did not do
    a good job. How effective would the right to counsel be if the Supreme Court had not
    taken us from A to B? Which interpretation do we think the Framers of the Sixth
    Amendment intended? Does that matter?

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