Document ID: s3://data.kl3m.ai/documents/govinfo/USCOURTS/USCOURTS-ca10-16-06092/USCOURTS-ca10-16-06092-0/pdf.json

Parties Involved:
Nicholas Joseph Ramirez
Appellant
United States of America
Appellee

Document Text:

UNITED STATES COURT OF APPEALS 

FOR THE TENTH CIRCUIT 

_________________________________ 

UNITED STATES OF AMERICA, 

 Plaintiff - Appellee, 

v. 

NICHOLAS JOSEPH RAMIREZ, 

 Defendant - Appellant. 

No. 16-6092 

(D.C. Nos. 5:15-CV-00016-R and 

5:12-CR-00090-R-1) 

(W.D. Okla.) 

_________________________________ 

ORDER DENYING A CERTIFICATE OF APPEALABILITY

_________________________________ 

Before HARTZ, O’BRIEN, and PHILLIPS, Circuit Judges. 

_________________________________ 

The United States District Court for the Western District of Oklahoma denied 

Defendant Nicholas Ramirez’s motion for relief under 28 U.S.C. § 2255. It also denied a 

certificate of appealability (COA). Defendant then filed a request for a COA with this 

court. See 28 U.S.C. § 2253(c)(1)(B) (requiring a COA to appeal denial of relief under § 

2255). We deny his request and dismiss the appeal. 

Defendant and 21 others were indicted on 147 counts related to a drug conspiracy. 

Defendant was indicted on 12 counts, which charged drug conspiracy (count 1), moneylaundering conspiracy (count 2), violation of the Travel Act (count 27), attempted 

distribution of ecstasy (counts 32 and 100), distribution of ecstasy (count 101), and 

money laundering (counts 103–108). Under an agreement with the prosecution, ten 

counts were dismissed and Defendant pleaded guilty to conspiracy to distribute 

FILED 

United States Court of Appeals 

Tenth Circuit 

October 21, 2016

Elisabeth A. Shumaker 

Clerk of Court

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 1 
2 

controlled dangerous substances (count 1), see 21 U.S.C. § 846, and conspiracy to 

launder proceeds of the drug conspiracy (count 2), see 18 U.S.C. § 1956(h). As part of 

the agreement, he waived his right to appeal or to collaterally challenge his conviction or 

sentence. On July 1, 2013, the court sentenced him to 180 months’ imprisonment (later 

reduced to 151 months under Amendment 782 to the United States Sentencing 

Guidelines) and three years of supervised release. 

Defendant contends that his trial counsel was ineffective in four respects: (1) 

failing to object to the quantity of marijuana attributed to Defendant in his presentence 

report; (2) failing to advise him that he could contest the chemical composition of the 

ecstasy pills attributed to him in the plea agreement; (3) failing to inform him that his 

conviction could increase his sentence in a case pending in California; and (4) 

misinforming him about the sentence he was facing by incorrectly estimating his sentence 

and by failing to inform him of the effects of a possible managerial-role enhancement and 

his misdemeanor convictions on his guidelines sentencing range. He also challenges the 

district court’s denial of his request for an evidentiary hearing. 

We can grant a COA only if the movant “has made a substantial showing of the 

denial of a constitutional right.” 28 U.S.C. § 2253(c)(2). This standard requires “a 

demonstration that . . . includes showing that reasonable jurists could debate whether (or, 

for that matter, agree that) the [motion] should have been resolved in a different manner 

or that the issues presented were adequate to deserve encouragement to proceed further.” 

Slack v. McDaniel, 529 U.S. 473, 484 (2000) (internal quotation marks omitted). In other 

words, the movant must show that the district court’s resolution of the constitutional 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 2 
3 

claim was either “debatable or wrong.” Id. If the motion was denied on procedural 

grounds, the movant faces a double hurdle. Not only must the movant make a substantial 

showing of the denial of a constitutional right, but he must also show “that jurists of 

reason would find it debatable whether the district court was correct in its procedural 

ruling.” Id. “Where a plain procedural bar is present and the district court is correct to 

invoke it to dispose of the case, a reasonable jurist could not conclude either that the 

district court erred in dismissing the [motion] or that the [movant] should be allowed to 

proceed further.” Id. 

Before addressing the merits we consider the effect of the waiver in Defendant’s 

plea agreement. The waiver states that “defendant in exchange for the promises and 

concessions made by the United States in this plea agreement, knowingly and voluntarily 

waives his right to . . . [a]ppeal or collaterally challenge his guilty plea, sentence and 

restitution imposed, and any other aspect of his conviction . . . .” United States v. 

Ramirez, No. CR-12-090-R, Plea Agreement at 9 (W.D. Okla. Sept. 6, 2012), ECF No. 

365. A waiver of the right to bring a collateral attack in a plea agreement is enforceable 

so long as (1) the collateral attack falls within the scope of the waiver; (2) the defendant 

knowingly and voluntarily waived his right to collateral review; and (3) enforcing the 

waiver would not result in a miscarriage of justice. See United States v. Hahn, 359 F.3d 

1315, 1325 (10th Cir. 2004) (en banc) (per curiam) (reviewing waiver of appellate 

rights); United States v. Cockerham, 237 F.3d 1179, 1183 (10th Cir. 2001) (enforceability 

of waiver of right to bring collateral attack is assessed under the same standard as a 

waiver of appellate rights). A miscarriage of justice occurs when (1) “the district court 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 3 
4 

relie[s] on an impermissible factor such as race”; (2) “ineffective assistance of counsel in 

connection with the negotiation of the waiver renders the waiver invalid”; (3) “the 

sentence exceeds the statutory maximum”; or (4) “the waiver is otherwise unlawful.” 

Hahn, 359 F.3d at 1327 (internal quotation marks omitted). Moreover, under what is 

called the Cockerham exception, “a plea agreement waiver of postconviction rights does 

not waive the right to bring a § 2255 petition based on ineffective assistance of counsel 

claims challenging the validity of the plea or the waiver.” Cockerham, 237 F.3d at 1187. 

Defendant’s first claim—that his counsel failed to object to the quantity of 

marijuana attributed to him in the presentence report—is barred by his waiver. The claim 

falls squarely within the waiver, and Defendant does not argue that his counsel’s failure 

to object to the quantity of marijuana made his waiver unknowing or involuntary, or that 

enforcing the waiver would result in a miscarriage of justice. Nor does this claim qualify 

for the Cockerham exception because it challenges only the sentencing, not the validity of 

the plea or the waiver. See id. at 1188. (To the extent that Defendant is arguing that his 

counsel should have had the ecstasy pills chemically tested for purposes of sentencing, 

that claim is likewise waived.) 

Defendant’s sole argument to overcome the waiver is based on a 2014 

memorandum by the Deputy Attorney General counseling federal prosecutors not to 

obtain such waivers, and not to enforce previously executed waivers (such as 

Defendant’s) “when defense counsel rendered ineffective assistance resulting in prejudice 

or when the defendant’s ineffective assistance claim raises a serious debatable issue that a 

court should resolve.” Memorandum from James M. Cole, Deputy Attorney General, to 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 4 
5 

All Federal Prosecutors (Oct. 14, 2014); Aplt. App. at 130 (reproducing the 

memorandum). An argument is forfeited, however, if not properly preserved in district 

court. See United States v. Teague, 443 F.3d 1310, 1314 (10th Cir. 2006). To be sure, 

we can review forfeited arguments for plain error, see id., but a plain-error argument is 

waived unless the appellant requests plain-error review in this court and puts forward 

arguments concerning its application. See United States v. Bustamante-Conchas, No. 15-

2025, 2016 WL 4183827, at *3 (10th Cir. Aug. 8, 2016). Here, Defendant failed to raise 

the Cole memorandum in district court, and he has not asked for plain-error review on 

appeal. Further, the memorandum was not in the district-court record; Defendant inserted 

it in his appellate appendix in violation of the appellate rules. See Fed. R. App. P. Rule 

30(a) (composition of the appendix); see also id. at 10(a) (composition of the record on 

appeal). We therefore do not address the issue. 

Defendant’s remaining three ineffective-assistance claims are not waived by the 

plea agreement because they attack the validity of his plea. To prevail on these claims, 

Defendant must show that his counsel’s representation fell below an objective standard of 

reasonableness and that counsel’s deficiency actually prejudiced him. See Strickland v. 

Washington, 466 U.S. 668, 687 (1984). When challenging a guilty plea, proving 

prejudice requires Defendant to “show that there is a reasonable probability that, but for 

counsel’s errors, he would not have pleaded guilty and would have insisted on going to 

trial.” Hill v. Lockhart, 474 U.S. 52, 59 (1985). 

Defendant’s first challenge to his plea arises from the alleged failure of his counsel 

to inform him that he could contest the chemical composition of the ecstasy pills 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 5 
6 

attributed to him before stipulating to the quantity of pills in his plea agreement, thereby 

“render[ing] his plea wholly uninformed.” Aplt. Br. at 15. Defendant asserts that if 

counsel had tested the pills and discovered that they were not pure MDMA (the shorthand 

for methylenedioxymethamphetamine, which is the active ingredient in ecstasy pills), his 

applicable guidelines sentencing range would have been lower. But Defendant bears the 

burden of proving that counsel’s performance caused him prejudice, see Strickland, 466 

U.S. at 694, and he has produced no evidence that testing the pills would have resulted in 

lowering his guidelines range. All he says is that “the pills from California that were 

used as the stipulated drug amount for sentencing purposes in Oklahoma contained BZP 

[1-benzylpiperazine] according to the lab reports of the Government.” Aplt. Br. at 16. 

This information does not help Defendant. It indicates that a sample of the pills he was 

charged with were in fact tested; yet he does not provide a calculation based on those test 

results that would require a lower guidelines range. We also note that the stipulated 

quantity of pills in the plea agreement is less than a third of the quantity set forth in his 

presentence report, suggesting that a chemical test would have been irrelevant to his 

decision to plea. See Hill, 474 U.S. at 59. 

Defendant’s second challenge to his plea arises from the alleged failure of his 

counsel to warn him of the potential consequences of his plea on pending proceedings in 

the Eastern District of California, where he had been indicted on similar drug and moneylaundering charges. His concern is that his conviction in this case could increase his 

eventual sentence in California by increasing his criminal-history points for a future 

computation of his guidelines sentence. But that prospect is highly unlikely. In 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 6 
7 

calculating Defendant’s guidelines sentencing range in the California case, Defendant’s 

conviction in this case would be considered a “prior sentence” only if it was “not part of 

the instant offense.” USSG §4A1.2(a)(1). The guidelines commentary explains that 

“[c]onduct that is part of the instant offense means conduct that is relevant conduct to the 

instant offense.” USSG. § 4A1.2 n.1. That is the situation here. Defendant asserts that 

he “was indicted not only in Oklahoma, but also in the federal district for the Eastern 

District of California as part of the same underlying drug and money laundering 

conspiracy.” Aplt. Br. at 10. And the point was not disputed in district court. As the 

court said in denying relief on this claim, “[I]n light of the representations of the parties 

that the California charges are related to the Oklahoma charges and the language of the 

relevant sentencing guidelines, Defendant’s contention that prejudice is apparent is 

without merit.” United States v. Ramirez, No. 15-16-R, Order at 8 (W.D. Okla. Feb. 17, 

2016), ECF No. 972. Not only was Defendant not prejudiced by his attorney’s failure to 

advise him of this remote possibility, but his attorney was also not ineffective for failing 

to inform him of a highly unlikely repercussion of his plea. 

In his third challenge to his plea, Defendant argues that his counsel misled him by 

predicting a sentence between six and ten years if he pleaded guilty versus 16 or more 

years if he went to trial; failed to inform him that he could receive a managerial-role 

enhancement to his offense level1

; and failed to inform him about the impact of his prior 

 

1

 Later in his brief, Defendant admits that his counsel informed him of the managerialrole enhancement. See Aplt. Br. at 19 (“the plea agreement itself was silent as to whether 

[the managerial-role] enhancement would be imposed, and trial counsel simply told 

Ramirez that the issue would be ‘argued at sentencing’”). Perhaps he is saying only that 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 7 
8 

misdemeanor convictions on his criminal-history computation. But ordinarily an 

erroneous sentencing estimate does not in itself render counsel’s performance 

constitutionally deficient. See United States v. Silva, 430 F.3d 1096, 1099 (10th Cir. 

2005). And in any event, the cumulative effect of counsel’s alleged errors could not have 

resulted in prejudice to Defendant by misleading him about his sentencing exposure. He 

was informed in his plea agreement and at the plea hearing that he was facing a 

maximum sentence of 20 years for each of the two counts to which he pleaded guilty, and 

that the sentence he would receive would be solely within the control of the district judge. 

Finally, Defendant challenges the district court’s denial of his request for an 

evidentiary hearing. We review that denial for an abuse of discretion. See United States 

v. Moya, 676 F.3d 1211, 1214 (10th Cir. 2012). Defendant has failed to allege that he 

could have presented relevant evidence at a hearing; he failed even to allege facts that 

could entitle him to relief. Because, he has not shown that an evidentiary hearing would 

serve a purpose, there was no abuse of discretion. 

Reasonable jurists could not debate the merits of the denial of Defendant’s § 2255 

motion. We DENY his request for a COA and DISMISS his appeal. 

Entered for the Court 

Harris L Hartz 

Circuit Judge 

 

counsel did not adequately explain the potential effect of the enhancement on his 

sentence. 

Appellate Case: 16-6092 Document: 01019708636 Date Filed: 10/21/2016 Page: 8