Leo Parrino v. United States of America

NOT RECOMMENDED FOR FULL-TEXT PUBLICATION
File Name: 16a0389n.06
No. 15-5921
UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT
LEO PARRINO,
Petitioner-Appellant,
v.
UNITED STATES OF AMERICA,
Respondent-Appellee.
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ON APPEAL FROM THE
UNITED STATES. DISTRICT
COURT FOR THE WESTERN
DISTRICT OF KENTUCKY
Before: COOK and KETHLEDGE, Circuit Judges; SARGUS, District Judge.*
KETHLEDGE, Circuit Judge. Pharmacist Leo Parrino pled guilty to a federal
misdemeanor for introducing and delivering misbranded inhalation drugs into interstate
commerce. As a result of his conviction, he cannot participate in any federal healthcare program
for five years. Parrino petitioned the district court to set aside his conviction, arguing that he
would not have pled guilty had he known that his conviction would effectively prevent him from
working as a pharmacist. The district court denied Parrino’s petition and we affirm.
I.
Parrino began working as a pharmacist in 1974. In 2002, he went to work for National
Respiratory Services, where he was responsible for preparing and mixing pharmaceutical
ingredients to create respiratory medications. In 2008, an FDA investigator audited National
Respiratory and found that it was distributing extremely subpotent doses of budesonide, a steroid
* The Honorable Edmund A. Sargus, Jr., Chief Judge of the United States District Court
for the Southern District of Ohio, sitting by designation.

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suspension used in inhalers to treat asthma and chronic obstructive pulmonary disease. The FDA
investigator found company records showing that in 2005, National Respiratory had tested
samples of its budesonide and found that much of it was subpotent and that some of it was
superpotent. National Respiratory had shipped this defective (and thus misbranded) budesonide
to patients in over a dozen states. Many of the misbranded budesonide doses were billed to
Medicare.
In 2009, federal investigators contacted Parrino, who in 2006 had moved on to work as a
pharmacist for K-Mart. According to the investigators, they specifically asked Parrino whether
National Respiratory had shipped any subpotent or superpotent batches. Parrino said that any
such batches had been destroyed before they were shipped to patients. The investigators
returned later in the year. They asked him again whether National Respiratory had shipped any
defective batches of budesonide, and again Parrino denied that he had. They then showed
Parrino the company’s own lab reports indicating that its budesonide was defective. Parrino then
changed his story: he admitted that he knew National Respiratory had shipped some defective
budesonide and that he had told National Respiratory’s COO about the problem. At the end of
the interview, he prepared and signed a handwritten statement acknowledging that, while he
worked as National Respiratory’s pharmacist, he was aware that he had prepared defective
(misbranded) budesonide that the company later shipped to patients.
In making that concession, Parrino had admitted to participation in a federal crime under
21 U.S.C. § 331(a), which prohibits the delivery of misbranded drugs into interstate commerce.
Violations are punishable by up to a year in prison, or three years if the act is committed with the
“intent to defraud and mislead[.]” 21 U.S.C. § 333(a)(1)-(2). In May 2010, lawyers from the
U.S. Attorney’s office in Louisville met with Parrino and his lawyer, Kenneth Plotnik. They told

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Parrino that they hoped to secure his cooperation in a criminal case against National
Respiratory’s COO. If Parrino cooperated, the government would charge him with a
misdemeanor violation of the law against misbranding; if Parrino refused, he would face a felony
prosecution and could be held liable for over $2 million in restitution.
The next day, according to Plotnik, he and Parrino met to discuss Parrino’s options.
Again according to Plotnik, Parrino was “extremely distraught . . . and he was unwilling to really
even discuss [possible] defenses very much. He was going to plead guilty to the misdemeanor,
and if there were consequences, we would deal with them later.” Parrino, according to Plotnik,
was well aware that there would be collateral consequences if he pled guilty to the misdemeanor
charge, including the possible revocation of his pharmacist’s license by the Kentucky Board of
Pharmacy.
He knew that coming in. He also knew that there was some—there
was another thing called this statute that would expel him from
prescribing. He knew there was a statute out there. He knew there
was some federal—he had either done some research between the
year after he had been contacted by the agents and he contacted
me, or maybe he [knew] it from his continuing pharmaceutical
education, but he knew that there was this exclusion statute
associated with a fraud conviction and most—but we definitely
knew about this.
Plotnik thereafter researched the federal statute in question, 42 U.S.C. § 1320a-7, which
instructs the Secretary of Health and Human Services to exclude (for five years) certain
individuals and entities from participation in any federal health-care program on a mandatory or
permissive basis, depending on certain conditions, such as whether the excluded person has been
convicted of certain crimes or has had his license suspended by a state licensing authority. See
42 U.S.C. § 1320a-7. Plotnik became convinced that Parrino would fit within the terms of the
“permissive” portion of the statute, so that it would be up to the Secretary’s discretion whether

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Parrino was barred from participating in federal health-care programs. About one month after
Parrino and Plotnik met with the U.S. Attorney’s office, Plotnik advised Parrino that Parrino
“was going to be in this permissive section and not in this mandatory exclusion section . . . of
course, I couldn’t guarantee that they wouldn’t exclude him because even under the permissive
section, exclusion was still a possibility.”
Thus, according to Plotnik, Parrino and Plotnik had discussed the possibility that
“[Parrino] could lose his license. He could lose the ability to prescribe medication. But
[Parrino] was adamant that he would not . . . face trial [for] the felony. He would not do it.”
Plotnik was interested in exploring defenses for Parrino: “I wanted to take it to trial. I thought
there were problems—constitutional problems with [the case].” But “Parrino was very unwilling
to discuss defenses.” Plotnik thereafter went about negotiating a plea that would downplay
Parrino’s role in the criminal conduct at National Respiratory, as part of a “strategy . . . both for
the purpose of the Board of Pharmacy and for the exclusion statute, to minimize [Parrino’s]
activities or behaviors.” Parrino eventually pled guilty to the misdemeanor misbranding charge
in September 2011. The date of his sentencing was dragged out by continuances, and Plotnik
wrote in emails to Parrino that this was a good thing: “this is going to postpone the day when
you are going to face any discipline from the Board of Pharmacy.”
In 2013, the district court sentenced Parrino to one year of probation and ordered him to
pay $14,000 in restitution. The Office of the Inspector General at the Department of Health and
Human Services later determined that Parrino’s five-year exclusion from federal programs was
mandatory. The Kentucky Board of Pharmacy also began investigating the possible revocation
of Parrino’s license. Parrino thereafter lost his job as a pharmacist at K-Mart.

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Parrino thereafter petitioned the district court to vacate his conviction because, he argued,
he would have risked trial rather than plead guilty had he known that he would face mandatory
exclusion from federal programs due to his misdemeanor conviction. He argued that Plotnik’s
failure to advise him that a misdemeanor conviction would likely subject him to mandatory
exclusion was constitutionally ineffective assistance of counsel, and that his guilty plea was
therefore defective. The district court held a hearing to consider Parrino’s claim. There, Parrino
testified that he “had no discussions with Mr. Plotnik regarding [the] potential collateral
consequences” of a guilty plea.
The district court denied Parrino’s petition after concluding that Plotnik’s alleged failure
to advise Parrino of the potential collateral consequences of his guilty plea did not violate
Parrino’s Sixth Amendment right to effective assistance of counsel. The court also concluded
that, even if Parrino did have a right to be advised of the collateral consequences of his plea,
Plotnik in fact fulfilled his obligation. The court found Plotnik’s testimony more credible than
Parrino’s, and held as a factual matter that “Plotnik made Parrino aware of the provisions of the
[exclusion] statute and its possible application to [Parrino] based upon the entry of his
misdemeanor guilty plea.” Finally, the court concluded that, even if Plotnik had failed to
properly advise Parrino of the collateral consequences, that omission did not prejudice Parrino,
because it would have been objectively unreasonable for Parrino to pass up the plea deal he
received and instead face a felony trial and a potential restitution award of $2.4 million. This
appeal followed.
II.
We review the district court’s legal conclusions de novo and its factual findings for clear
error. See United States v. Jackson, 181 F.3d 740, 743-44 (6th Cir. 1999). We afford “great

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deference” to the district court’s credibility determinations. United States v. Grubbs, 773 F.3d
726, 731 (6th Cir. 2014).
The Sixth Amendment guarantees that “[i]n all criminal prosecutions, the accused shall
enjoy the right to . . . the Assistance of Counsel for his defence.” U.S. Const. amend. VI
(emphasis added). The right to counsel is not a right to competent legal advice regarding all
aspects of the accused’s life. Rather, it is a right to “Assistance” in a particular type of legal
proceeding—the “criminal prosecution[.]” Id. That right stems from the recognition that, in an
adversarial trial, “access to counsel’s skill and knowledge is necessary to accord . . . ample
opportunity to meet the case of the prosecution[.]” Strickland v. Washington, 466 U.S. 668, 685
(1984).
A guilty plea, however, is a “break in the chain” of criminal proceedings. Tollett v.
Henderson, 411 U.S. 258, 267 (1973). The integrity of the criminal-justice system requires the
presumption that the plea is final. So “[w]hen a criminal defendant has solemnly admitted in
open court that he is in fact guilty of the offense with which he is charged . . . [h]e may only
attack the voluntary and intelligent character of the guilty plea by showing that the advice he
received from counsel was not within the standards” of effective representation required by the
Sixth Amendment. Id.
Thus, an argument that counsel rendered constitutionally-ineffective assistance in
advance of trial is an argument that counsel was so ineffective that the defendant either pled
guilty involuntarily, pled guilty without awareness of the elements of the crime he committed, or
pled guilty without awareness of potentially successful defenses to criminal liability. Cf. United
States v. Ruiz, 536 U.S. 622, 630 (2002) (noting that a knowing guilty plea “does not require
complete knowledge of the relevant circumstances”). Typically, a defendant’s failure to consider

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the numerous potential collateral consequences of a criminal conviction—e.g., prohibitions on
certain categories of employment, or future limitations on constitutional rights—does not vitiate
a guilty plea. See, e.g., United States v. Youngs, 687 F.3d 56, 61-63 (2d Cir. 2012); United States
v. Delgado-Ramos, 635 F.3d 1237, 1239-40 (9th Cir. 2011) (per curiam). In 2010, however, the
Supreme Court held that counsel’s failure to advise a criminal defendant that a guilty plea would
lead to his deportation voided the defendant’s guilty plea so long as the defendant would
reasonably have proceeded to trial but for counsel’s failure. See Padilla v. Kentucky, 559 U.S.
356, 374 (2010). Parrino argues that the rule expressed in Padilla should apply to his case, and
that Plotnik therefore had a duty to advise Parrino of the potential collateral consequences of
Parrino’s plea, including the risk that Parrino would be barred from participating in federal
health-care programs. Parrino asserts that Plotnik neglected that duty and that Parrino’s guilty
plea was thus entered involuntarily.
Apart from the common ground of attorney advice, however, Parrino’s case has little in
common with Padilla’s. The holding in Padilla was limited to advice “concerning the specific
risk of deportation” and was based upon a long tradition that placed deportation in “close
connection to the criminal process,” which made deportation “uniquely difficult to classify as
either a direct or a collateral consequence.” Id. at 366. The Padilla Court also noted the
particularly “harsh consequences of deportation.” Id. at 360. The penalty of complete
banishment from the United States is different in kind from the burden of five years’ exclusion
from federal health-care programs.
Yet even assuming for the sake of argument that Plotnik had a duty to advise Parrino of
the collateral regulatory consequences of Parrino’s guilty plea, Plotnik fulfilled that duty here by
thoroughly discussing with Parrino the potential collateral consequences of a guilty plea. Parrino

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says those discussions were not sufficient because Plotnik did not tell Parrino that he was
guaranteed to be subject to “mandatory exclusion.” Parrino Br. at 23 (quoting Plotnik’s
testimony). But Parrino demands much more of Plotnik than the Court asked of defense counsel
in Padilla. There, the Court required that counsel have a “rudimentary understanding of the
deportation consequences of a particular criminal offense” so that he would “be able to plea
bargain creatively with the prosecutor in order to craft a conviction and sentence that reduce the
likelihood of deportation[.]” Padilla, 559 U.S. at 373. The Padilla Court required further that
counsel advise his client whether his plea carries the “risk” of deportation. Id. at 374. Here,
Plotnik thought Parrino fit within the “permissive” exclusion provision, and crafted a plea
agreement written to minimize Parrino’s culpability and persuade the Office of the Inspector
General at the Department of Health and Human Services—which administers the exclusion
statute—that Parrino deserved to continue practicing as a pharmacist. Plotnik’s strategy was a
reasonable one: defendants who are convicted of misdemeanor misbranding, as Parrino was, are
sometimes subject to the permissive exclusion provision contained in 42 U.S.C. § 1320a-7(b).
See Friedman v. Sebelius, 686 F.3d 813, 817 (D.C. Cir. 2012). But Plotnik warned Parrino that
there was still a real risk of exclusion: “I couldn’t guarantee that they wouldn’t exclude him.”
Plotnik’s advice met the standard for effective assistance of counsel articulated in Padilla.
The district court’s judgment is affirmed.

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