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United States District Court, Southern District of New York

June 24, 2002


The opinion of the court was delivered by: Leisure, District Judge.


Petitioner Freddie Parrado, acting pro se, moves for a reduction of his sentence pursuant to 28 U.S.C. § 2255. In the alternative Parrado claims that his guilty plea was neither knowingly nor voluntarily entered. For the following reasons, Parrado's petition is denied.


A. Factual and Procedural History

On July 17, 1996, the Grand Jury filed an indictment, charging Parrado with distributing and possessing with intent to distribute five kilograms and more of mixtures and substances containing a detectable amount of cocaine in violation of 21 U.S.C. § 846. Thereafter, Parrado waived formal indictment, and on July 2, 1997, the government issued a superceding information S2 96 Cr. 505(PKL) (the "Information") charging him with the same violation of 21 U.S.C. § 846.

On June 30, 1997, Parrado entered into a plea agreement with the government. See Plea Agreement of Freddie Parrado, June 30, 1997 (the "Plea Agreement"). The plea agreement stipulated that he distributed and possessed with intent to distribute at least 15 but less than 50 kilograms of cocaine. See Plea Agreement at 2. Further, the plea agreement established that his base offense level was 34 under the Federal Sentencing Guidelines (the "Sentencing Guidelines"). See id. Due to Parrado's cooperation, however, the parties stipulated to reducing the base offense level to 31. See id. at 2-3. His criminal history included seven points and a rating of IV under the Sentencing Guidelines. See id. at 3. The parties stipulated that his sentencing range was 151 to 188 months. See id. at 4.

On July 2, 1997, Parrado pleaded guilty to the violation of 21 U.S.C. § 846, before The Honorable John F. Keenan, United States District Judge in this Court. See Parrado's Plea Allocution, July 2, 1997 (the "Plea Allocution"), at 15. On February 4, 1998, I sentenced Parrado to 151 months in prison. See Transcript of Parrado's Sentencing, February 4, 1998 (the "Sentencing Transcript"), at 9. During the plea allocution Judge Keenan fully complied with the requirements of Rule 11(c) of the Federal Rules of Criminal Procedure then construed by the courts. In this regard, Judge Keenan carefully discussed with the defendant the veracity of his guilty plea, and inquired as to whether Parrado understood the charges against him. See Plea Allocution at 4 and 7. Judge Keenan also explained the possible sentencing range Parrado faced, detailed the terms of a mandatory supervised release and explained that the sentencing judge may depart from the Sentencing Guidelines. See id. at 10. Next, Judge Keenan inquired, "Are you offering a plea of guilty of your own free will?" Parrado answered, "Yes." See id. at 14. Judge Keenan specifically inquired whether Parrado understood the terms of the plea agreement, to which Parrado responded affirmatively. See id. at 13.

B. Petitioner's Claims

Parrado claims that his sentence is invalid under the new rule of Apprendi v. New Jersey because the judge rather than the jury determined the quantity of narcotics involved. See 530 U.S. 466, 120 S.Ct. 2348, 147 L.Ed.2d 435 (2000). Parrado also attempts to rely on Jones v. United States, 530 U.S. 1271, 120 S.Ct. 2739, 147 L.Ed.2d 1002 (2000). See Parrado's Reply to The Government's Memorandum In Opposition to Parrado's § 2255 Motion ("Parrado's Reply"). Further, Parrado asserts that he pleaded guilty and was "convicted of 5 kilos; not the 15 to 50 that he was sentenced for." Parrado's Reply at 7. In the alternative, petitioner alleges that his guilty plea was not voluntary or knowing. See id. at 4.


I. Timeliness of the Petition

Section 2255 sets forth the following time restrictions:

A 1-year period of limitation shall apply to a motion under this section. The limitation period shall run from the latest of:

(1) the date on which the judgment of conviction becomes final;

(2) the date on which the impediment of making a motion created by governmental action in violation of the Constitution or laws of the United States is removed, if the movant was prevented from making a motion by such governmental action;

(3) the dates on which the right asserted was initially recognized by the Supreme Court and made retroactively applicable to cases on collateral review; or

(4) the date on which the facts supporting the claim or claims presented could have been discovered through the exercise of due diligence.

28 U.S.C. § 2255.

Parrado initiated his claim more than 3 years after the conclusion of the case. Judgment was entered on February 5, 1998, and Parrado filed his Section 2255 motion on March 10, 2001. Thus, Parrado fails to meet the time restriction of Section 2255(1).

Parrado attempts to take advantage of Section 2255(3). He claims the "new rule" of Apprendi provides the relief he seeks and was issued less than one year prior to filing his motion. Section 2255 clearly announces, however, that the right recognized must be applicable retroactively to be used as a weapon for a collateral attack, and thus, as detailed below, because Apprendi is not retroactively applicable, Parrado can not take advantage of the Apprendi decision in the instant motion.

II. The Retroactivity of Apprendi

The Second Circuit recently heard arguments regarding the retroactivity of Apprendi, but has not yet rendered its decision. See Beatty v. United States, 293 F.3d 627, 631 n. 3 (2d Cir. 2002) (citing United States v. Luciano (Parise), No. 01-1198 (2d Cir. argued Jan. 28, 2002)). The Supreme Court also has not ruled on this issue.

The Apprendi Court held that, "[o]ther than the fact of a prior conviction, any fact that increases the penalty for a crime beyond the prescribed statutory maximum must be submitted to a jury, and proved beyond a reasonable doubt." 530 U.S. at 490, 120 S.Ct. 2348. The issue of retroactivity turns on whether the rule is considered procedural or substantive. While substantive rules are automatically applied retroactively, holdings dictating methods of criminal procedure, such as the Apprendi holding, are presumptively non-retroactive. See Rosario v. United States, No. 00 Civ. 9695, 2001 WL 1006641, at *2 (S.D.N.Y. Aug. 30, 2001); Teague v. Lane, 489 U.S. 288, 310, 109 S.Ct. 1060, 103 L.Ed.2d 334 (1989); see also Bousley v. United States, 523 U.S. 614, 619-20, 118 S.Ct. 1604, 140 L.Ed.2d 828 (1998) (holding that procedural rules are presumptively non-retroactive). A majority of the courts that have considered Apprendi's retroactivity have presumed the rule to be procedural. See e.g., United States v. Sanders, 247 F.3d 139, 147 (4th Cir. 2001) (holding the language of Apprendi dictates that rule is procedural); Raulston v. Menifee, No. 01 Civ. 0406, 2002 WL 826810, at *4 (S.D.N.Y. Apr. 30, 2002) (concluding that the rule of Apprendi is procedural). Indeed, the language of the Apprendi Court strongly suggests that the rule at issue is procedural. "The substantive basis for New Jersey's enhancement is thus not an issue; the adequacy of New Jersey's procedure is." Apprendi, 530 U.S. at 475, 120 S.Ct. 2348. This Court is persuaded by the weight of authority and the language set forth in Apprendi itself, and thus holds that the rule is procedural.

A decision affecting criminal procedure becomes retroactive for the purpose of collateral review in one of two ways. The Supreme Court designates the rule as retroactive, or the rule satisfies an exception set forth in Teague. 489 U.S. at 311, 109 S.Ct. 1060; see Tyler v. Cain, 533 U.S. 656, 665, 121 S.Ct. 2478, 150 L.Ed.2d 632 (2001).

The first Teague exception states, "that a new rule should be applied retroactively if it places `certain kinds of primary, private individual conduct beyond the power of the criminal law.'" 489 U.S. at 311, 109 S.Ct. 1060 (citations omitted). The second exception is for procedural rules that are "implicit in the concept of ordered liberty," id. (citation omitted), or "watershed rules of criminal procedure implicating the fundamental fairness and accuracy of the criminal proceeding." Tyler, 533 U.S. at 665, 121 S.Ct. 2478 (quoting Graham v. Collins, 506 U.S. 461, 478, 113 S.Ct. 892, 122 L.Ed.2d 260 (1993)).

The Supreme Court has not made the new rule announced in Apprendi retroactive. See Forbes v. United States, 262 F.3d 143, 145 (2d Cir. 2001) (per curiam). Moreover, Courts in the Southern District of New York have largely held that the Apprendi holding does not fit either of the two exceptions set forth in Teague, and therefore is not retroactively applicable on collateral review. See Raulston, 2002 WL 826810, at *4 (holding that Apprendi does not apply on collateral review); Fiumara v. United States, 198 F. Supp.2d 427, 431 & n. 5 (S.D.N.Y. Apr. 3, 2002) (Sprizzo, J.) (same); Saldarriaga v. United States, No. 99 Civ. 4487, 2002 WL 449651, at *5 (S.D.N.Y. Mar. 21, 2002) (same); Garcia v. United States, No. 01 Civ. 7188, 2002 WL 42888, at *1 (S.D.N.Y. Jan. 11, 2002) (same). But see Rosario, 2001 WL 1006641, at *2 (ruling that Apprendi is substantive in nature and therefore retroactive). Though the Second Circuit has not specifically considered the issue,*fn1 the Fourth, Eighth, Ninth, and Eleventh Circuits have all ruled that Apprendi does not apply retroactively on collateral review. See, e.g., Sanders, 247 F.3d at 147-51 (holding that the Apprendi decision is not applicable on collateral review); United States v. Moss, 252 F.3d 993, 997 (8th Cir. 2001) (same); Jones v. Smith, 231 F.3d 1227, 1238 (9th Cir. 2000) (same); McCoy v. United States, 266 F.3d 1245, 1257-58 (11th Cir. 2001) (same).

The majority of courts that have considered the issue have ruled Apprendi is not retroactive under the first exception, because Apprendi does not place any behavior outside the scope of the criminal law. See Sanders, 247 F.3d at 148; Raulston, 2002 WL 826810, at *4. The second exception also does not apply. Designation as a "watershed" rule or a procedural rule that "is implicit in the concept of ordered liberty" is rare. United States v. Mandanici, 205 F.3d 519, 529 (2d Cir. 2000), cert. denied, 531 U.S. 879, 121 S.Ct. 190, 148 L.Ed.2d 132 (2000). A rule is considered a watershed rule when the failure to adopt it will increase the risk of an innocent defendant being convicted or the rule "alter[s] our understanding of the bedrock of procedural elements" that are essential to a fair trial. Teague, 489 U.S. at 311, 109 S.Ct. 1060. As the government argues in the instant action, absence of the rule set out in Apprendi does not threaten the fundamental fairness of trial or create a risk that an innocent party will be convicted. See The Government's Memorandum In Opposition to Parrado's § 2255 Motion at 17. To the contrary, Apprendi places the burden of determining elements that lead to sentence enhancement on the jury rather than the judge. 530 U.S. at 490, 120 S.Ct. 2348.

In Bilzerian v. United States, the Second Circuit held that shifting an element of proof from the judge to the jury did not constitute a watershed rule, and therefore was not applicable on collateral review. 127 F.3d 237, 241 (2d Cir. 1997) (McLaughlin, J.) (holding that juries will likely not have substantially different interpretations than judges). Accordingly, the rule set forth in Apprendi, which does no more than shift the proof of drug quantity from the judge to the jury, does not meet either of the Teague exceptions, and therefore is not retroactively available for collateral attack in the instant motion.

Parrado attempts to, circumvent this proposition by arguing in the alternative that the ruling of Jones v. United States, 530 U.S. 1271, 120 S.Ct. 2739, 147 L.Ed.2d 1002 (2000), is retroactively applicable on collateral attack, thus making his instant Section 2255 motion timely. The Court in Jones remanded the case so that the Tenth Circuit could apply the new holding set forth by Apprendi. In United States u Jones[II], 235 F.3d 1231 (10th Cir. 2000), the Tenth Circuit simply applied the rule set forth in Apprendi.

Parrado's Jones argument fails for two reasons. First, the holding of Jones[II] is not a new right recognized by the Supreme Court.*fn2 Second, there is no reason to believe that a subsequent ruling applying Apprendi's holding would be retroactive, when Apprendi is not.

III. Application of Apprendi to Parrado's Case

Even if the Apprendi holding applied on collateral review, Parrado's appeal would still fail, because Apprendi does not apply to the instant situation. Apprendi is applicable only when a judge decides an element of the crime that would lead to an enhanced sentence. See e.g., United States v. Norris, 281 F.3d 357, 361 (2d Cir. 2002) (Newman, J.); United States v. Guevara, 277 F.3d 111, 118 (2d Cir. 2001); United States v. Thomas, 274 F.3d 655, 663 (2d Cir. 2001). Guevara holds that a sentence is erroneous when a judge determines a drug quantity that exposes the defendant to a minimum sentence exceeding the top of the Sentencing Guidelines range that would have been applicable absent the judge's finding. 277 F.3d at 119. In Norris, the Second Circuit clarified that at the other end of the sentencing spectrum, Apprendi only applies to situations where a judicial determination enhances a sentence beyond the statutory maximum. Id. at 360; see also Thomas, 274 F.3d at 663 (ruling that Apprendi is applicable only when a judicial determination enhances a sentence above the statutory maximum that would have controlled absent such a determination). Thus, Apprendi is not applicable to a judicial fact finding that leads to Sentencing Guideline enhancements that remain under the statutory maximum. See Norris, 281 F.3d at 361.

Parrado fails to prove that his sentence was enhanced or that a judge determined the drug quantity. Parrado was informed that he was charged with conspiracy to violate 21 U.S.C. § 841(a)(1) and 841(b)(1)(A), which constitutes distributing and possessing with intent to distribute 5 kilograms or more of cocaine. Further, Parrado pleaded guilty to this crime and stipulated to the elements of the crime, including that he had distributed and possessed with intent to distribute at least 15 but less than 50 kilograms of cocaine.

The fact that Parrado distributed and intended to possess at least 15 but less than 50 kilograms was not explicitly charged in the Information, which simply charged Parrado with intent to distribute 5 and more kilograms of cocaine. The Supreme Court has held that the indictment must charge any fact that enhances the sentence. United States v. Cotton, ___ U.S. ___, 122 S.Ct. 1781, 1783, 152 L.Ed.2d 860 (2002) (citing Apprendi, 530 U.S. at 476, 120 S.Ct. 2348). Cotton, however, only requires that the indictment charge a threshold level that includes within it the sentence that the defendant received. Id., 122 S.Ct. at 1786 n. 3. In the present case the Information charges "5 kilograms and more," which carries a maximum penalty of life imprisonment under the statutory guidelines of 21 U.S.C. § 841(b)(1)(A). See Information at 1. Thus, the Information charges the threshold level of the sentence that Parrado received. Moreover, Parrado's failure to allege the Information was defective at the time of his trial waives any right that he had to challenge the Information. See id., 122 S.Ct. at 1787 (holding that a failure to object to the error in the indictment at trial waives a right to challenge the indictment at a latter stage in the proceedings).*fn3

Finally, the judge did not determine the drug quantity — Parrado himself determined the quantity in his plea agreement. See Plea Agreement at 2. Therefore, the very principle upon which Apprendi is based is absent, because there was no judicial determination of drug quantity.

Assuming arguendo that the judge had determined drug quantity, Parrado's claim still fails because he was not subject to a sentence enhancement under the most liberal construction of either Guevara or Norris. Parrado alleges he should have been sentenced to distributing and possessing with intent to distribute 5 kilograms of cocaine. Under Guevara, Apprendi remains inapplicable because the statutory minimum is the same for a sentence based on 15 to 50 kilograms and a sentence based on 5 kilograms. See 21 U.S.C. § 841(b)(1)(A). Therefore, it does not enhance the statutory minimum beyond the Sentencing Guidelines range that would have been applicable. Apprendi remains inapplicable under Norris because Parrado was sentenced to 151 months in prison, which is within the statutory range of a minimum penalty of 120 months and a maximum of life imprisonment. See id. Thus, Apprendi is not applicable because Parrado's sentence has not been enhanced under either of the standards set forth in Norris or Guevara.

IV. Parrado's Plea Agreement

A. Parrado's Contention that the Plea was neither Knowing nor Voluntary

Parrado contends that his guilty plea was not voluntarily or knowingly entered because of an intervening change in law. See Parrado's Reply at 7. He seeks to rely on the authority of Salas v. United States, which holds that a defendant may argue that his plea was not knowing or voluntary when an intervening change in law occurs. 139 F.3d 322, 324-25 (2d Cir. 1998). The facts stipulated in the plea agreement, however, are binding, and the petitioner is only allowed to contest whether the stipulated facts constitute a crime in light of the change in law. See id. Because Apprendi and Jones dictate that the quantity of narcotics is an element to be decided by the jury, and because Parrado's guilty plea is the equivalent of a jury decision on quantity, the change in law has no affect on the instant situation. See Libretti v. United States, 516 U.S. 29, 38, 116 S.Ct. 356, 133 L.Ed.2d 271 (1995) (holding that entering a guilty plea is an admission of guilt and a waiver of the right to jury trial).

Further, Parrado's guilty plea was knowingly and voluntarily entered because there was no error in the "Court Advice" delivered at his plea allocution. See United States v. Vonn, ___ U.S. ___, 122 S.Ct. 1043, 1046, 152 L.Ed.2d 90 (2002) (ruling that Rule 11 is used to ensure the knowing and voluntary nature of a plea); United States v. Maher, 108 F.3d 1513, 1520 (2d Cir. 1997) (quoting United States v. Parkins, 25 F.3d 114, 117 (2d Cir. 1994)) (holding that the district court must strictly comply with Rule 11 so that it can be determined whether the plea is knowingly and voluntarily entered). Although Parrado has made no other complaint regarding the voluntariness of his plea other than the above discussed grounds, a review of the transcript of Parrado's plea allocution in its entirety shows beyond peradventure that it was voluntarily and willingly made. "Before accepting a plea of guilty . . . the court must address the defendant personally in open court and inform the defendant of, and determine that the defendant understands" the charges before him, as well as, his constitutional rights. Fed.R.Crim.P. 11(c). Judge Keenan carefully covered with the defendant every aspect of Rule 11 applicable at the time of sentencing. See Plea Allocution at 3-14. Therefore, Parrado's plea was both knowingly and voluntarily entered.

B. The Plea Agreement's Prohibition of Appeals

Parrado's plea agreement states that Parrado would "neither appeal, nor otherwise litigate under 28 U.S.C. § 2255, any sentence within or below the stipulated Guidelines range." Plea Agreement at 5. So long as, Parrado's plea was knowing and voluntary he cannot bring the instant appeal, because it would violate his plea agreement. Indeed, a defendant may waive his or her right to appeal through a plea agreement. As the Second Circuit explained in United States v. Salcido-Contreras:

[i]n no circumstance, however, may a defendant, who has secured the benefits of a plea agreement and knowingly and voluntarily waived the right to appeal a certain sentence, then appeal the merits of a sentence conforming to the agreement. Such a remedy would render the plea bargaining process and the resulting agreement meaningless.

990 F.2d 51, 53 (2d Cir.) (per curiam), cert. denied, 509 U.S. 931, 113 S.Ct. 3060, 125 L.Ed.2d 742 (1993); see also Santobello v. New York, 404 U.S. 257, 260-62, 92 S.Ct. 495, 30 L.Ed.2d 427 (1971) (holding that a voluntary and knowing plea agreement is equivalent to a contract and the promises stated within must be fulfilled by the parties). Parrado knowingly and voluntarily waived his right to appeal. The record is clear that Judge Keenan complied with Rule 11.*fn4 The case law at the time held that a defendant must knowingly and voluntarily waive their right to appeal. "[A] waiver of the right to appeal should only be enforced by an appellate court if the record `clearly demonstrates' that the waiver was both knowing . . . and voluntary." United States v. Ready, 82 F.3d 551, 557 (2d Cir. 1996) (citations omitted). Judge Keenan questioned, "Do you remember that the terms of the plea agreement were read to you by an interpreter . . .?" Plea Allocution at 13. Parrado answered that he did. See id. Moreover, Judge Keenan asked, "And were the terms of the plea agreement explained to you and do you understand them?" Id. Again Parrado answered, "Yes." Id. Thus, it is clear from the record that Parrado understood the consequences of pleading guilty and knowingly and voluntarily waived his right to an appeal. In any event, the issue is moot because as detailed above, Parrado's opportunity to appeal has lapsed due the fact that the Apprendi ruling is not retroactively applicable.


For the foregoing reasons, Parrado's petition to reduce his sentence pursuant to 28 U.S.C. § 2255 is HEREBY DENIED.


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