Case Name: UNITED STATES of America, Appellee, v. Philip ROSSILLO, Defendant-Appellant
Court: United States Court of Appeals for the Second Circuit
Jurisdiction: United States
Decision Date: 1988-08-11
Citations: 853 F.2d 1062
Docket Number: No. 1164, Docket 87-1437
Parties: UNITED STATES of America, Appellee, v. Philip ROSSILLO, Defendant-Appellant.
Judges: Before VAN GRAAFEILAND, PIERCE and ALTIMARI, Circuit Judges.
Reporter: Federal Reporter 2d Series
Volume: 853
Pages: 1062–1071

Head Matter:
UNITED STATES of America, Appellee, v. Philip ROSSILLO, Defendant-Appellant.
No. 1164, Docket 87-1437.
United States Court of Appeals, Second Circuit.
Argued May 10, 1988.
Decided Aug. 11, 1988.
Louis M. Freeman, New York City (Freeman, Nooter & Ginsberg, New York City, of counsel), for defendant-appellant.
Michael A. Guadagno, Asst. Attorney-In-Charge, Brooklyn, N.Y. (Andrew J. Ma-loney, U.S. Atty., E.D.N.Y., Edward A. McDonald, Attorney-In-Charge, U.S. Dept, of Justice, Organized Crime Strike Force, E.D.N.Y.), for appellee.
Before VAN GRAAFEILAND, PIERCE and ALTIMARI, Circuit Judges.

Opinion:
ALTIMARI, Circuit Judge:
Defendant-appellant Philip Rossillo appeals from a judgment of conviction under 18 U.S.C. § 1962(d), following a plea of guilty entered in the United States District Court for the Eastern District of New York (Bramwell, J.). Rossillo argues in this appeal that the district court erred in refusing to grant his motion pursuant to Fed.R.Crim.P. 32(d) to withdraw his plea of guilty prior to sentencing. Because the court failed to ensure that the plea of guilty was voluntarily and knowingly entered as required by Fed.R.Crim.P. 11, we vacate defendant's guilty plea.
BACKGROUND
The indictment charged Philip Rossillo and twenty-four others with, inter alia, conspiracy to commit a RICO violation, 18 U.S.C. § 1962(d). After extensive plea negotiations between Rossillo's counsel and the government, a plea agreement was reached providing that Rossillo's sentence would not exceed fourteen years and that Rossillo would be allowed to bring relevant facts regarding his medical condition to the court's attention before sentencing.
On June 9, 1986, the fourteen defendants, including Rossillo, who had agreed to plead guilty to the RICO violation appeared before Judge Bramwell. Before accepting the guilty pleas, the district court advised the defendants as a group of their constitutional rights, the nature of the charges against them and the consequences of their pleas. Afterwards, Judge Bramwell inquired whether the defendants understood that the court could ask them questions about the offenses to which they offered to plead guilty. The court then asked each defendant individually what his answer was to its question. When it was Rossillo's turn to respond, he said "Yes, Your Hon- or." This procedure was followed throughout the plea proceedings. The court also informed defendants that if their pleas of guilty were accepted, there would be no trial and that they would be waiving this constitutional right. Rossillo indicated that he understood the consequences of his guilty plea.
Judge Bramwell then proceeded to determine the factual basis for the pleas by reading the relevant portions of the indictment to which the defendants were pleading. Since each defendant was charged with a different combination of racketeering acts, each attorney advised the court as to those acts his respective client would admit guilt. After Rossillo's attorney informed the court of the specific predicate acts with which Rossillo was charged, the district court asked Rossillo if the facts underlying the alleged predicate acts were true. Rossillo admitted that they were true. Next, the district court asked the defendants if they had been threatened or coerced in any way into pleading guilty. All of the defendants, including Rossillo, answered no. The district court then inquired whether defendants were under the influence of any drug, alcohol or other substance:
The Court.- At the present time, here and now, are you under the influence of any drug, alcohol or other intoxicants?
sj: ifc :}:
The Court: Mr. Philip Rossillo?
[Mr. Freeman]: Your Honor, this is an exceptional circumstance.
The Court: He has — his heart condition.
[Mr. Freeman]: Yes.
The Court: Thank you.
Finally, the court asked the defendants how they pleaded to the racketeering conspiracy count as charged in Count One of the indictment. Rossillo pleaded guilty.
At the conclusion of the proceedings, the court stated that it found a factual basis for the pleas and accordingly accepted the pleas of guilty to Count One as to each of the defendants including Rossillo, whose sentencing was postponed due to his deteriorating medical condition. Almost a year later, on May 8, 1987, Rossillo moved before sentencing to withdraw his plea pursuant to Fed.R.Crim.P. 32(d). Rossillo claimed that the court did not comply with Rule 11. The court found, however, that the Rule 11 requirements were satisfied and that there was "no evidence that [Ros-sillo's heart] condition or medical treatment in any way impaired his . guilty plea." On July 17, 1987, the district court, therefore, denied Rossillo's motion to withdraw his plea.
According to the terms of his plea agreement, Rossillo then was given an opportunity to present before the court testimony regarding his medical condition and the effects of a lengthy term of incarceration on his physical health. After hearing the testimony on September 16, 1987, the court sentenced Rossillo to fourteen years imprisonment.
DISCUSSION
Rossillo contends on this appeal that in accepting his plea of guilty, the district court did not comply with the requirements of Fed.R.Crim.P. 11. Specifically, he argues that he was under the influence of medication rendering him unable to enter a voluntary and knowing guilty plea, and that the district court erred in failing to inquire whether the medication affected the voluntariness of his plea. Because in this case we believe that the district court should have inquired further into Rossillo's ability to offer his plea before finding that it was voluntarily and knowingly entered, we agree with defendant that his guilty plea must be vacated.
Before accepting a plea of guilty, Rule 11 requires that the district judge determine whether the defendant "understands the nature of the charge against him and whether he is aware of the consequences of his plea." McCarthy v. United States, 394 U.S. 459, 464, 89 S.Ct. 1166, 1170, 22 L.Ed. 2d 418 (1969); see Fed.R.Crim.P. 11. The district court must "satisfy itself that the defendant is offering the plea voluntarily and that he is competent to understand the nature of the charge, his constitutional rights, and the scope of the penalty provided by law." Saddler v. United States, 531 F.2d 83, 85 (2d Cir.1976) (per curiam) (citations omitted). The Supreme Court has declared that a plea of guilty "cannot support a judgment of guilt unless it [is] voluntary in a constitutional sense." Henderson v. Morgan, 426 U.S. 637, 644-45, 96 S.Ct. 2253, 49 L.Ed.2d 108 (1976); see Saddler, 531 F.2d at 86 ("plea may be accepted only if the waiver is found to be voluntar[il]y and intelligently given"). A plea may be involuntary because the defendant does not understand that he is waiving constitutional rights or because the defendant has such an incomplete understanding of the charge that his plea cannot stand as an intelligent admission of guilt. Henderson, 426 U.S. at 645 n. 13, 96 S.Ct. at 2257 n. 13. Not only must the plea of guilty be voluntary, it must also be a knowing and intelligent act done with "sufficient awareness of the relevant circumstances and likely consequences." Brady v. United States 397 U.S. 742, 748, 90 S.Ct. 1463, 1469, 25 L.Ed. 2d 747 (1970).
In McCarthy, the Supreme Court set forth two purposes of Rule 11:
First, . it is designed to assist the district judge in making the constitutionally required determination that a defendant's guilty plea is truly voluntary. Second, the Rule is intended to produce a complete record at the time the plea is entered of the factors relevant to this voluntariness determination.
394 U.S. at 465, 89 S.Ct. at 1170. The Court noted that constitutional principles lie behind the rule, since a defendant who pleads guilty waives several fundamental constitutional rights. Id. at 466, 89 S.Ct. at 1170. Consequently, in order for the waiver to be valid under the due process clause, it must be " 'an intentional relinquishment or abandonment of a known right or privilege.' " Id. (quoting Johnson v. Zerbst, 304 U.S. 458, 464, 58 S.Ct. 1019, 1023, 82 L.Ed. 1461 (1938)).
In rejecting the government's argument that the district court could assume that the defendant understood the charges against him, the McCarthy Court stressed the need for "on the record" determinations of defendant's understanding. Thus, the Court held that the district court could not make outside-the-record assumptions about defendant's ability to understand the nature of the proceedings because Rule 11 mandates that the district court personally interrogate the defendant. Personally questioning the defendant not only aids the court in determining the voluntariness of the guilty plea, it also serves to aid that determination in any post-conviction proceeding based on a claim that the plea was not voluntary. McCarthy, 394 U.S. at 467, 89 S.Ct. at 1171; see United States v. Gonzalez, 820 F.2d 575, 579 (2d Cir.1987) (per curiam) (explaining that faithful observance of Rule 11 eliminates basis for later claim by defendant that plea was defective).
In asserting that his plea was not knowingly and intelligently made, Rossillo contended before Judge Bramwell, as he does on appeal, that the court failed to determine whether he was taking medication that impaired his ability to understand the nature of the charges against him and the consequences of his plea. The district court refused to credit Rossillo's contention that he failed to understand the nature of the proceedings when he pleaded guilty since the underlying plea agreement was, in the court's words, the product of "complex and lengthy negotiations." The government argues that the district court made every effort to "expose[ ] the defendant's state of mind on the record through personal interrogation," McCarthy, 394 U.S. at 467, 89 S.Ct. at 1171, and that Rossillo and his attorney were obliged to bring any information relating to impairment to the court's attention.
Although the district court personally interrogated Rossillo, an on-the-record determination was not made concerning whether Rossillo was under the influence of any medication, drug or intoxicant. Instead, when the district judge asked Rossillo for a response to its question, the court simply alluded to defendant's heart condition. Judge Bramwell never received a definitive "yes" or "no" answer from defendant. By acknowledging Rossillo's heart condition, the district court apparently assumed that defendant's condition did not interfere with his mental capabilities. As McCarthy makes clear, however, Rule 11 is not satisfied unless the district court determines the voluntariness of the guilty plea based upon on-the-record responses to its questions. See also Irizarry v. United States, 508 F.2d 960, 964 (2d Cir.1974) (stressing that to the extent district judge " 'resorts to "assumptions" not based upon recorded responses to his inquiries,' " he fails to comply with Rule 11) (quoting McCarthy, 394 U.S. at 467, 89 S.Ct. at 1171).
We have recognized previously that district judges must strictly adhere to the requirements of Rule 11 in order to ensure the voluntariness of guilty pleas. United States v. Gonzalez, 820 F.2d 575 (2d Cir.1987) (per curiam); United States v. Saft, 558 F.2d 1073 (2d Cir.1977); United States v. Journet, 544 F.2d 633 (2d Cir.1976). In Journet, we stated that the district court must "personally inform the defendant in open court of specifically enumerated rights and other matters pertaining to the question of whether the plea is a voluntary and knowing one." 544 F.2d at 635. In view of the fact that a defendant's constitutional rights were at stake, we refused to accept the government's contention that failure to comply could be treated as harmless error and observed that Rule 11 requires " 'the utmost solicitude of which courts are capable in canvassing the matter with the accused to make sure he has a full understanding of what the plea connotes and of its consequences.' " Id. at 636 (quoting Boykin v. Alabama, 395 U.S. 238, 243-44, 89 S.Ct. 1709, 1712, 23 L.Ed.2d 274 (1969)); see Kercheval v. United States, 274 U.S. 220, 223, 47 S.Ct. 582, 583, 71 L.Ed. 1009 (1927). In Soft, we explained that while Rule 11 does not require slavish adherence to the precise wording of the statute when the court informs the defendant of his constitutional rights, Rule 11 does require that each of its detailed elements be covered with defendant during the plea allocution. 558 F.2d at 1079. In Gonzalez, we again stated the necessity of strict adherence to Rule 11:
There should be no doubt after Joumet that on a direct criminal appeal there will be little room for minimizing the effect of a failure to comply with Rule 11.... The policies behind Rule 11 are important and should be strictly enforced.
820 F.2d at 578 (quoting Del Vecchio v. United States, 556 F.2d 106, 109 (2d Cir.1977)). The Gonzalez court held that, in view of defendant's argument that he pleaded guilty because his attorney promised him a sentence of probation, the failure of the district court to ask defendant whether his plea was "not the result of . promises apart from a plea agreement," Fed.R.Crim.P. 11(d), required that the plea be vacated. In so holding, we emphasized that it was important for the district court to "flush out any discussions that have occurred regarding the possible sentence a defendant may receive and to dispel any belief a defendant may have that any promise or promise-like representation made to him by anybody is binding on the court." 820 F.2d at 579.
In this case, the district court's failure to further question defendant about any medication he was taking for his heart condition, the possible effects that that medication might have on his decision to plead guilty, and his ability to understand the plea proceedings, dictates, consistent with our prior holdings in Joumet, Soft and Gonzalez, that we once again reaffirm our commitment to strict compliance with Rule 11. We believe that if there is any indication, as there was in this case, that defendant is under the influence of any medication, drug or intoxicant, it is incumbent upon the district court to explore on the record defendant's ability to understand the nature and consequences of his decision to plead guilty. We know of no other way to ensure both that defendant understands the constitutional rights that he is relinquishing by pleading guilty and that the plea is truly voluntary. See McCarthy, 394 U.S. at 465, 89 S.Ct. at 1170.
The duty of a district court to inquire further when defendant's ability to understand the nature of the plea proceedings is at issue was recently addressed by the Third Circuit. In United States v. Cole, 813 F.2d 43 (3d Cir.1987), in response to the district judge's question whether defendant was under the influence of any medication or drug, Cole stated that he had taken some drugs the previous night. The district court in Cole never questioned defendant as to the possible effects of the recent drug use on his competence to plead guilty. Relying on the Supreme Court's decision in McCarthy, the Third Circuit explained that defendant's affirmative answer called into question his ability to make an intelligent and competent waiver of his constitutional rights. Id. at 46; see McCarthy, 394 U.S. at 466-67, 89 S.Ct. at 1170-71. Thus, the court held that
Rule 11 counsels a district court to make further inquiry into a defendant's competence to enter a guilty plea once the court has been informed that the defendant has recently ingested drugs or other substances capable of impairing his ability to make a knowing and intelligent waiver of his constitutional rights.
813 F.2d at 46.
We believe that the Third Circuit's holding in Cole argues persuasively here for requiring the district court, before finding that Rossillo's plea was voluntarily and knowingly entered, to have inquired further into defendant's state of mind once the court was alerted that defendant might be under the influence of medication. See also Saddler, 531 F.2d at 87 (pointing to defendant's unresponsive answers to the court's inquiries as "warning flags" indicating that defendant may not have been competent to plead guilty); United States v. Thomas, 468 F.2d 422, 426 (10th Cir.1972) ("record must show that the trial judge personally asked the proper questions and received answers from the accused indicating his awareness of the charge against him and the consequences of his guilty plea") (emphasis added), cert. denied, 410 U.S. 935, 93 S.Ct. 1389, 35 L.Ed.2d 599 (1973); cf. United States v. Auen, 846 F.2d 872, 877-78 (2d Cir.1988) (bizarre behavior of defendant requires that district court make contemporaneous on-the-record findings of defendant's competence to stand trial). Consequently, we specifically reject the government's argument that defendant or his counsel was obliged to elaborate on the "exceptional circumstance[s]" that Rossillo's situation presented. Rule 11 directs the court to determine that the plea is voluntary. Fed. R.Crim.P. 11(e), (d). The rule places no such burden on the defendant. Indeed, as the Supreme Court in McCarthy observed, before the 1966 amendments to Rule 11, not all district judges personally interrogated defendants. It was to alter this procedure that Congress expressly placed the duty of inquiry on the court. See 394 U.S. at 465-66, 89 S.Ct. at 1170-71. In addition, the fact that the underlying plea agreement was the result of "complex and lengthy negotiations" is of no consequence. The point is not whether defendant was competent to enter into plea negotiations but rather whether, at the time of the plea allocution, he was able to understand the nature and consequences of his decision to plead guilty.
Due to the large number of defendants before the district judge at the plea hearing, we appreciate the difficulty of explicit compliance with Rule 11. However, because the constitutional rights of each defendant are at stake, the district court must be scrupulous in determining on the record whether defendant's guilty plea was voluntarily and intelligently offered. Otherwise, the plea "has been obtained in violation of due process and is therefore void." McCarthy, 394 U.S. at 466, 89 S.Ct. at 1171.
CONCLUSION
The district court failed to receive a direct response to its question concerning whether Rossillo was under the influence of any medication, drug or other substance. The court apparently assumed that, although defendant had a heart condition, he nevertheless was competent to enter a plea of guilty. We find, however, that the failure to make an on-the-record determination whether Rossillo was under the influence of any medication, and, if he had taken any medication, whether his plea was voluntarily and knowingly offered, constitutes reversible error. Accordingly, in light of the constitutional principles involved and the need for careful compliance with Rule 11, we conclude that defendant's guilty plea and conviction cannot stand. Defendant's guilty plea, therefore, is vacated, and the case is remanded to the district court for further proceedings consistent with this opinion.
Vacated and remanded.
Circuit Judge VAN GRAAFEILAND dissents in a separate opinion.