*Of the Northern District of California, sitting by

designation.

United States Court of Appeals

For the First Circuit

No. 99-1899

UNITED STATES,

Appellee,

v.

JOSE SANTO a/k/a FEDERICO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. William G. Young, U.S. District Judge]

[Hon. Robert B. Collings, U.S. Magistrate Judge]

Before

 Torruella, Chief Judge,

Campbell, Senior Circuit Judge,

and Schwarzer,* Senior District Judge.

Jonathan R. Saxe with whom Twomey & Sisti Law Offices was

on brief for appellant.

Michael J. Pelgro, Assistant United States Attorney, with

whom Donald K. Stern, United States Attorney, James B. Farmer,

Assistant United States Attorney, Chief, Criminal Division,

Stephen P. Heymann, Assistant United States Attorney, Deputy

Chief, Criminal Division, and Michael J. Pelgro, Assistant

United States Attorney, were on brief for appellee.
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September 15, 2000

CAMPBELL, Senior Circuit Judge. Defendant-appellant

Jose Santo pled guilty to drug conspiracy and other charges

after being told -- incorrectly, as it turned out -- that he

faced a statutory mandatory minimum sentence of only five years.

Later, upon determining that Santo was responsible for more

drugs than was initially contemplated, the district court

sentenced him subject to the ten-year mandatory minimum

applicable to the greater drug quantity. Santo contends that

the court’s understatement of the mandatory minimum penalty

rendered his guilty plea involuntary, as the error both violated

an express provision of Fed. R. Crim. P. 11 requiring advice as

to the mandatory minimum penalty provided by law and also

affected his substantial rights. See Fed. R. Crim. P. 11(c)(1)

and (h). We agree, and allow Santo to withdraw his plea.

I.

On December 3, 1998, Santo and three co-defendants were

charged with conspiracy to distribute heroin, 21 U.S.C. § 846,

and the distribution of heroin, 21 U.S.C. § 841(a)(1). Santo

was also charged with making false statements to a federal law

enforcement officer, 18 U.S.C. § 1001, and making false
1The plea agreement was of the sort authorized by Fed. R.

Crim. P. Rule 11(e)(1)(B), under which the government’s

recommendation or request contained in the agreement does not

bind the court, and the defendant may not withdraw his plea

should the court decline to accept the government’s

recommendation or request. See Fed. R. Crim. P. 11(e)(2).

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statements in a passport application, 18 U.S.C. § 1542.

Thereafter, Santo signed a plea agreement with the United States

Attorney, in which he agreed to plead guilty to all the counts

against him in the indictment and admitted that he was, in fact,

guilty of each of these offenses.1 
-4-

A. The plea agreement

The plea agreement included a statement of Santo’s

mandatory minimum and maximum penalties. Count One, the

conspiracy charge, was said to have

a maximum of 40 years and a mandatory

minimum of 5 years, in federal prison

without parole, to be followed by a term of

supervised release of at least 4 years, a

fine of up to $2,000,000, and a special

assessment of $100,000.

The distribution counts were each said to provide, inter alia,

for a maximum of twenty years imprisonment, and the false

statement counts, inter alia, twenty years and five years

respectively. 

The plea agreement went on to announce that the parties

“will take the following positions at sentencing under the

United States Sentencing Guidelines”:

The parties agree to take the position in

connection with the drug counts that Santo

is accountable for at least 100 grams of

heroin, that his Base Offense Level is 26

(100-400 grams of heroin), and the five year

minimum mandatory provision is applicable.

After reference to an agreed four-level upward adjustment for

being an organizer or leader under U.S.S.G. § 3B1.1(a), the

parties agreed to take the position that the “safety valve”

provision was inapplicable and that Santo’s adjusted offense

level on the drug counts was 30. The parties agreed to an
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adjusted offense level of 10 on the two false statements counts,

and to a possible three-level reduction for acceptance of

responsibility under U.S.S.G. § 3B1.1, subject to certain

conditions. 

The plea agreement next contained a section entitled

“Sentence Recommendation,” which read as follows: “The U.S.

Attorney takes no position at this time concerning his sentence

recommendation before the district court . . .“ In this section

the parties agreed there was no basis for departure from the

range established by the sentencing guidelines, except possibly

for substantial assistance under U.S.S.G. § 5K1.1. The plea

agreement further provided: 

7. Court Not Bound By Agreement

The sentencing recommendations made by the

parties and their respective calculations

under the Sentencing Guidelines are not

binding upon the U.S. Probation Office or

the sentencing judge. Within the maximum

sentence which Santo faces under the

applicable law, the sentence to be imposed

is within the sole discretion of the

sentencing judge. Santo’s plea will be

tendered pursuant to Fed. R. Crim. P.

11(e)(1)(B). Santo may not withdraw his

plea of guilty regardless of what sentence

is imposed. Nor may Santo withdraw his plea

because the U.S. probation office or the

sentencing judge declines to follow the

Sentencing Guidelines calculations or

recommendations of the parties.

B. The Rule 11 hearing
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On April 22, 1999, the district court conducted a

change of plea hearing pursuant to Fed. R. Crim. P. 11 for Santo

and one of his co-defendants. The parties filed the

abovementioned written plea agreement with the court. The

district court explained the nature of the charges and the

rights that Santo was giving up by pleading guilty. Santo, who

participated in the hearing via an interpreter, responded that

he understood. 

Consistent with the plea agreement, the court told

Santo that he faced a mandatory minimum sentence of five years’

imprisonment and a maximum sentence of forty years: 

Now let’s talk about what may happen here if

you plead guilty. When Congress passes a

law they pass a maximum possible sentence.

And the maximum sentence here for the crime

of distribution of heroin is twenty years in

prison . . . On the conspiracy charges,

because the government in your case, Mr.

Santo, says more drugs are attributable to

you, the maximum sentence is potentially

–well, the maximum sentence is, the maximum,

forty years in prison . . . and I have to

give you five years in prison, there’s a

mandatory minimum sentence.

[Emphasis supplied.] The court made no mention of the

possibility of a higher statutory mandatory minimum in the event

that a greater quantity of drugs was attributed to Santo.

Noting that Santo’s other charges could be sentenced
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consecutively, the court stated that it could add up all of his

charges to a maximum of 185 years, or life imprisonment.

The court then turned to the sentencing guidelines: 

Now, I’ll ask Mr. Pelgro [the Assistant

United States Attorney] . . . what he thinks

the range is in each case. I turn to him

not because he governs the range, I’ll

figure out what the range is, but I’ll

listen to him, I’ll listen to your

attorneys, I’ll listen to you, I’ll listen

to the probation officer, but you need to

know that he thinks the range is because

probably he’s the person who is looking for

the most severe sentence.

[Emphasis supplied.] The government responded: [W]e believe

that Mr. Santo will come out, or we think he’ll come out at

total offense level 27 . . .” The government went on to state

that the guideline sentencing range was 87 to 108 months

(approximately seven to nine years), based on a criminal history

category of III. The court then addressed Santo:

Now, Mr. Santo, listening to Mr. Pelgro, he

says that the way he now calculates the

sentencing guidelines, you’re looking at a

minimum 87 months in prison and a maximum

108 months. Is that how you understand it?

Mr. Santo: Yes.

Shortly thereafter, the court stated:

In each case, gentlemen, you must understand

that I am no part of the plea bargain; that

I will impose the sentence I think is

appropriate under the law. I’m not agreeing

to go along with anything. I will follow

the law and impose what I think is an
2At first, the PSR set forth a minimum sentence of five

years and a maximum of forty years. On July 27, 1999, that was

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appropriate sentence. Do you understand

that, Mr. Santo?

Mr. Santo: Yes. 

Santo stated that his plea was based on no inducements

other than the plea agreement. The district court found that

Santo knowingly, intelligently, and voluntarily exercised his

right to plead guilty. Before accepting Santo’s plea, the court

stated: “Understand, now, if you plead guilty there is no taking

it back or starting over.”

On or around June 28, 1999, the United States Probation

Office provided Santo’s counsel with a copy of the pre-sentence

report (PSR) pursuant to Fed. R. Crim. P. 32(b)(6)(A).

Probation found Santo responsible for 1000 to 6000 grams of

heroin, rather than the 100 to 400 grams contemplated in the

plea agreement and at the Rule 11 hearing. Pursuant to 21

U.S.C. §§ 841 and 846, these increased drug amounts raised

Santo’s mandatory penalties from five years minimum and forty

years maximum to ten years minimum and life maximum. In

addition, they raised Santo’s offense level to 33. See U.S.S.G.

§ 1B1.3. Applying a criminal history category of III, probation

recommended a sentence of 168 to 210 months, with a minimum

sentence of ten years and a maximum of life imprisonment.2 Santo
changed to a minimum sentence of ten years and a maximum of life

imprisonment.

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did not then file any objections to the PSR or move to withdraw

his plea.

C. The sentencing hearing

On July 27, 1999, the district court held a sentencing

hearing. The court addressed the discrepancies between the PSR

and the plea agreement and Rule 11 discussion:

Let me put on the record the additional

matter. I don’t think this is going to

impact the sentencing process as we go

forward, but the record should be complete

and the probation officers have

appropriately advised me. 

Upon the investigation post plea of the

probation department, it appears that the

quantity of drugs involved warrants a

statutory term of imprisonment of a minimum

of ten years and a maximum of life. At the

time of the plea, Mr. Santo was advised that

the maximum sentence he could face, if he

pleaded guilty, was 40 years in prison.

Therefore, I state, so everyone is clear on

it, if things eventuate such that justice

requires a sentence of more than 40 years,

without more, Mr. Santo will be entitled to

withdraw his plea and get his case in order

to stand for trial.

The court then grouped the various counts against Santo, applied

the upward and downward adjustments, and stated that the

sentencing range was 168 months to 210 months. The court asked

the government and Santo’s counsel if it had properly calculated
-10-

the sentence under the guidelines. Initially, Santo’s counsel

objected to the fact that the amount of drugs for which he was

responsible had been increased since his change of plea:

I have no problem with the calculations

based on the amount that’s estimated by

probation to be attributable to Mr. Santo.

The problem I have is that the plea

agreement was based on accounting only 100

grams to Mr. Santo’s activity. And his plea

and all the discussions and negotiations

were based on that level of a hundred grams

which would have started him at level 26 and

then done the adjustments. And that’s why,

again, I don’t question the math, but I

question the quantity that’s attributed to

him.

The district court acknowledged that a lesser drug quantity had

been negotiated, but stated that “[u]nder a sentencing

guidelines regime probation has done what it’s supposed to do

and has given me information that appears unchallenged, that the

drug quantity is substantially greater, and I’m, I’m disposed to

follow it.”

In response, Santo’s counsel stated: 

Let me just, one issue I didn’t – with

respect to this changing of the minimum and

maximum, I did address that earlier with my

client and anticipating your Honor’s ruling

I told him that’s probably what’s going to

happen so I’m not worried about that aspect

of it. . . . So I know that it is not

written in stone, that it’s not something

the defendant can count on, but as a

practical matter that’s basically what he

was counting on was a range closer to that
3In the alternative, Santiago seeks resentencing on the

separate ground that the amount of drugs upon which his sentence

was based was unsupported. Since we reverse on the first

ground, we do not reach this point.

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fully understanding that there’s a lot of

variables of things that won’t be known.

The district court responded that it was bound by the sentencing

guidelines and found that the drug quantities in the PSR were

accurate. It noted that Santo had preserved his rights with

respect to the court’s rulings and findings.

The government stated that it felt “bound to recommend

the low end of the guideline sentencing range, which is 168

months.” Santo did not seek to withdraw his guilty plea, but

rather asked to be sentenced at the low end of the range. The

district court sentenced Santo to 168 months (fourteen years)

incarceration. 

II.

On appeal, Santo seeks to withdraw his plea. He

contends that the district court’s understatement of the

statutory mandatory minimum sentence (as five years, rather than

the ultimately applicable ten years) violated Rule 11(c)(1)’s

explicit requirement that the court advise the defendant of “the

mandatory minimum penalty provided by law, if any.” Santo

further argues that the court’s error affected his substantial

rights.3 See Fed. R. Crim. P. 11(h).
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Before addressing these contentions, we note that Santo

did not request to withdraw his guilty plea in the district

court. This omission, however, is not necessarily fatal where

a fundamental mistake in Rule 11 procedure is asserted. 

Ordinarily, we deem an issue not raised

before the district court to be waived. We

will, however, determine compliance with

Rule 11, even if a claim of non-compliance

was not presented in the district court, if

the record is sufficiently developed, which

is generally the case because of Rule

11(g)'s requirement that the district court

make a complete record of the plea

proceedings. 

United States v. Noriega-Millan, 110 F.3d 162, 166 (1st Cir.

1997); see also United States v. McDonald, 121 F.3d 7, 10 (1st

Cir. 1997).

This is not to say that a defendant’s failure to seek withdrawal

of his plea in the district court is immaterial. We have said,

and reiterate, that a defendant who has not sought relief below

"faces a high hurdle" on appeal, and must show that there was "a

substantial defect in the Rule 11 proceeding itself." United

States v. Miranda-Santiago, 96 F.3d 517, 522 (1st Cir. 1996);

see also Fed. R. Crim. P. 11(h) (providing that "[a]ny variance

from the procedures required by this rule which does not affect

substantial rights shall be disregarded"). 

A. The district court’s error
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Fed. R. Crim. P. 11(c)(1) provides that 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 following:

(1) the nature of the charge to which the

plea is offered, the mandatory minimum

penalty provided by law, if any, and the

maximum possible penalty provided by law,

including the effect of any special parole

or supervised release term, the fact that

the court is required to consider any

applicable sentencing guidelines but may

depart from those guidelines under some

circumstances . . .

(Emphasis supplied.) Here, as to the most serious charge, drug

conspiracy, the government stated unequivocally in the plea

agreement that Santo faced a mandatory minimum sentence of five

years and a forty year maximum. The district court reiterated

those minimum and maximum figures at the Rule 11 hearing, again

without qualification or mention of the possibility of any

higher minimums and maximums should larger drug quantities be

found to be involved. 

The problem the court faced was that the applicable

mandatory minimum provided in the statute depended on the amount

of heroin for which Santo was found responsible. While the

court was correct as to the mandatory minimum applicable to

Santo under the then-assumed amounts, it was wrong as to the
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mandatory minimum ultimately applicable given the subsequent

increase in drug quantity. The court no doubt assumed that the

government, if anyone, would know what amounts should be

factored into the statutory equation. At the Rule 11 hearing,

the district court based its unqualified statement to Santo of

the statutory minimum and maximum on the drug quantity provided

by the government (100 to 400 grams). As this court has noted,

district courts often rely on the government’s representations

regarding facts material to the sentence, but there can be risk

in so doing, as this case demonstrates:

One might expect that whatever the

complexity of the Sentencing Guidelines, it

would be easy accurately to advise the

defendant of the statutory penalties. But

as this case shows, the statutory penalties

themselves are sometimes complicated; the

defendant may be charged with multiple

counts; and the penalties may depend on

information . . . that is not automatically

available to the district judge at the time

of the plea. Accordingly, district judges

often rely heavily, although not

exclusively, on the prosecutor to provide

the court with a description of statutory

penalties or at least to advise the court if

it misstates the terms.

United States v. Raineri, 42 F.3d 36, 40 (1st Cir. 1994). 

Where, as here, mandatory minimums and maximums depend

on drug quantity and drug quantity attribution is not finally

determined until after the plea process is completed, the court

is obviously in a tricky position when it comes to being able to
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accurately advise a defendant, as Rule 11 requires, of the

mandatory minimum and maximum penalties faced. See United

States v. Padilla, 23 F.3d 1220, 1223 (7th Cir. 1994). This

lack of certainty, however, does not relieve the court of its

Rule 11(c)(1) responsibility to correctly inform a defendant,

insofar as is possible, of those mandatory minimum and maximum

penalties applicable in his particular case. See id.; see also

United States v. Herndon, 7 F.3d 55, 58-59 (5th Cir. 1993). 

The dissent contends that Rule 11's requirement was

adequately met merely by informing Santo of the five-year

mandatory minimum applicable to the lesser drug quantities

recommended by the government in the plea agreement, even though

the court later found greater quantities resulting in a

mandatory ten-year minimum and sentenced him accordingly.

However, advice as to a mandatory minimum that is no longer

relevant can hardly achieve Rule 11's purpose, which is to

advise a defendant of the actual consequences of his plea so

that he can realistically decide whether to plead guilty. See

McDonald, 121 F.3d at 11-12. Here, the rule governing Santo’s

plea specifically disallowed Santo from withdrawing the plea

notwithstanding the court’s rejection of the government’s

recommended drug quantities in favor of quantifies triggering a

doubled mandatory minimum. See Note 1, supra. Thus, knowledge
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only of the mandatory minimum attributable to quantities

recommended by the government could not educate Santo as to the

full array of possible consequences his plea might engender. 

One way to ensure that a defendant is properly

informed, in the present circumstances, would be to advise as to

the different mandatory minimums and maximums that could apply,

depending on the quantity of drugs later attributed to the

defendant: 

[A] prudent district judge hearing a plea

from a defendant charged under an indictment

or information alleging a § 841(a) violation

but containing no [or ambiguous] quantity

allegation[s should] simply walk a defendant

through the statutory minimum sentences

prescribed in § 841(b) explaining that a

mandatory minimum may be applicable and that

the sentence will be based on the quantity

of drugs found to have been involved in the

offense with which the defendant is

charged.” It is not costly in time or

effort to enumerate during the plea colloquy

the several mandatory penalties potentially

applicable when attributable drug quantities

are uncertain. 

 

Padilla, 23 F.3d at 1224 (quoting United States v. Watch, 7 F.3d

422, 429 (5th Cir. 1993)).

Here, the district court announced minimum and maximum

penalties based exclusively on the drug quantity asserted at the

time by the government. Thus the court stated, “I have to give

you five years in prison, there’s a mandatory minimum sentence.”

It did not inform Santo that the statutory mandatory minimum and
4Although later in its colloquy the court was careful to

instruct that it was not bound by the sentencing guidelines, no

such cautionary statement accompanied its discussion of the

statutory mandatory minimum. Santo could have reasonably

believed, therefore, that while the contemplated guideline range

of 87 to 108 months was subject to change depending on the

court’s findings, the mandatory minimum would always be five

years.

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maximum sentences would change to ten years and life if Santo

were found responsible for a greater quantity of heroin.4 Hence,

as events turned out, the district court erred in informing

Santo of a mandatory minimum that was, in fact, only half as

long as that under the drug quantity later determined. See

Padilla, 23 F.3d at 1223; Herndon, 7 F.3d at 58-59. 

We hold, therefore, that the court failed to comply

with the express provisions of Rule 11(c)(1) when it incorrectly

advised Santo as to the minimum and maximum penalties that

applied in his case. See McDonald, 121 F.3d at 11 (court failed

to mention mandatory minimum); United States v. Gray, 63 F.3d

57, 60 (lst Cir. 1995) (court stated that ten years was maximum

sentence, when it in fact was mandatory minimum); United States

v. Lopez-Pineda, 55 F.3d 693, 695-696 (1st Cir. 1995) (court

failed to mention mandatory minimum). 

B. Impairment of substantial rights

Our determination that the district court erred in

failing to inform Santo of the correct, higher mandatory minimum
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applicable in his case does not end matters, however. Fed. R.

Crim. P. 11(h) provides: "Any variance from the procedures

required by this rule which does not affect substantial rights

shall be disregarded.” A guilty plea should be set aside only

for errors that implicate the "core concerns" of Rule 11, which

include the defendant's knowledge of the consequences of the

guilty plea. See Noriega-Millan, 110 F.3d at 166; Gray, 63 F.3d

at 60. We review the totality of the circumstances surrounding

Santo’s Rule 11 hearing to ascertain whether his substantial

rights were affected by the error. See United States v.

Cotal-Crespo, 47 F.3d 1, 4-5 (lst Cir. 1995).

Regarding the court’s failure to tell Santo that he

might be maximally sentenced to life imprisonment, rather than

just forty years, the district court, on its own initiative,

sought to correct that error at the sentencing hearing by

stating that Santo could withdraw his plea if a sentence of more

than forty years were found to be required. Because Santo’s

actual sentence did not exceed fourteen years, the scenario

mentioned by the court did not arise. Santo does not contend on

appeal that the court’s Rule 11 misstatement concerning the

potential maximum was, in light of what transpired at

sentencing, other than harmless error.
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The more difficult question is the impact of the

misstated mandatory minimum of five years rather than ten years.

At the Rule 11 hearing, as in the written plea agreement, the

prosecution openly declared that Santo’s probable guideline

sentence was 87 to 108 months, or approximately seven to nine

years. Such a sentence was compatible with a five-year

mandatory minimum but would be barred by a ten-year mandatory

minimum. While Santo was advised that the court was not bound

by the government’s proposed sentencing range, he received no

intimation at the Rule 11 hearing that the 87 to 108 month range

was too low to be statutorily lawful under the mandatory minimum

that ultimately was found to apply in his case. Nor was he told

that there was any possibility that a higher mandatory minimum

might control. The question, then, is whether Santo can be said

to have understood the consequences of his plea given the

district court’s failure to call to his attention, as Rule 11

requires, the mandatory minimum that actually came to apply in

his case. We conclude that it is sufficiently likely that Santo

misjudged the consequences of his plea in light of the court’s

misinformation so that he must be allowed to withdraw his plea.

The present situation is not unlike that in United

States v. Hernandez-Wilson, 186 F.3d 1 (1st Cir. 1999). There,

as here, the defendant was not advised that the government’s
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calculated sentence was legally unsustainable. In HernandezWilson, the government recommended a thirty-month sentence on

the condition that the defendant comply with the requirements of

the “safety valve” provision, which would permit the court to

sentence him below the mandatory minimum. See id. at 2.

Unbeknownst to both parties as well as the district court at the

time the defendant entered his guilty plea, the safety valve

provision was not available due to the defendant’s criminal

history; hence, he had no possibility of receiving a sentence

less than the sixty-month mandatory minimum. See id. at 4. We

held that the defendant could have reasonably misunderstood the

consequences of his guilty plea, which affected his substantial

rights. We allowed him to withdraw his guilty plea despite his

failure to raise the issue below. See id. at 5.

The case of Raineri, 42 F.3d at 36, is also

instructive, even though, there, the district court’s error was

found harmless. In Raineri, the defendant was told that he

faced potential imprisonment of thirty-five years and a maximum

fine of $20,000. The parties and the court were apparently

unaware that the defendant’s criminal history subjected him

instead to a minimum sentence of twenty years and a maximum of

forty-five years, plus a maximum fine of $25,000. See id. at

40-41. The district court later sentenced him to ten years’
5The government argues that the district court’s error in

this case should be considered harmless, as in McDonald, because

Santo’s sentence was calculated under the guidelines, without

reference to the statutory mandatory minimum. We do not find

this convincing. As Rule 11 implicitly recognizes, the

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imprisonment and ordered him to make restitution in the amount

of $5988. See id. at 40. Hence, the sentence the defendant

received (as well as the sentence discussed at the Rule 11

hearing) was shorter than the actual mandatory minimum. See id.

at 42. This court concluded that the defendant’s substantial

rights were not impaired by the misinformation, as there was “no

indication that the misinformation given to Raineri at the Rule

11 hearing led him to expect a lesser penalty than he actually

received.” Id.; see also McDonald, 121 F.3d at 11-12 (failure

to state mandatory minimum did not affect defendant’s

substantial rights where guideline sentencing range outstripped

applicable mandatory minimum and defendant could not have

reasonably hoped for shorter sentence).

Here, Santo reasonably could have expected from the

information given, including in particular the inaccurate fiveyear minimum, that he might receive a significantly lighter

punishment than the fourteen-year sentence he eventually

received. Unlike McDonald, the government calculated a sentence

of 87 to 108 months at the Rule 11 hearing, well under the

undisclosed mandatory minimum of ten years.5 It is true that
mandatory minimum may be relevant to the defendant’s

expectations regardless of the guideline sentencing range. See

McDonald, 121 F.3d at 11-12; see also Noriega-Millan, 110 F.3d

at 166. Moreover, the absence of prejudice in McDonald was

supported by the fact that the guideline range exceeded the

undisclosed mandatory minimum. As explained supra, this case

differs in that the stated guideline range was one to three

years shorter than the statutory mandatory minimum.

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Santo would have no valid complaint to a longer guideline

sentence based on a higher drug quantity, but he was entitled to

know that a higher drug quantity might lead to a doubled

mandatory minimum that would remove any possible discretion the

court might have retained to give a sentence below ten years.

The district court may have inadvertently further encouraged

Santo’s expectations of a shorter sentence by stating that

“probably [the prosecutor]’s the person who is looking for the

most severe sentence,” suggesting that Santo might reasonably

anticipate a sentence no greater than the one being discussed.

In any case, there was no suggestion from the government or the

court that an increase in drug quantity, besides affecting

Santo’s guideline range, would pose an insurmountable statutory

bar to sentences within the range discussed at the Rule 11

hearing. 

What occurred controverts the purpose behind Rule 11's

requirement that the district court inform a defendant of, and

determine that he understands, the applicable mandatory minimum
-23-

sentence. That purpose is “to ensure that the defendant is not

induced to change his plea because of a totally unrealistic

expectation as to how mild a sentence he might receive.”

McDonald, 121 F.3d at 11-12; see also Noriega-Millan, 110 F.3d

at 166. The misinformation that the minimum sentence was only

five years reasonably could have affected Santo’s decision to

change his plea to guilty. Cf. Hernandez-Wilson, 186 F.3d at 6;

Gray, 63 F.3d at 61. Had he known that a ten-year mandatory

minimum might apply, so as to preclude the sentencing range

discussed at the Rule 11 hearing, his expectations might

conceivably have been lessened, along with his willingness to

plead. We conclude, therefore, that the district court’s

erroneous advice as to the mandatory minimum sentence affected

Santo’s substantial rights, and we hold that Santo must be

permitted to withdraw his plea. See Hernandez-Wilson, 186 F.3d

at 6; Gray, 63 F.3d at 61. 

Reversed and remanded for further proceedings not

inconsistent with this opinion.

Dissent to follow.
-24-

SCHWARZER, Senior District Judge, dissenting. I

respectfully dissent. This appeal presents two issues: (1) Did

the district court fail to comply with Rule 11; and (2) if it

did, did the error impair Santo’s substantial rights.

(1) Rule 11 states that “the court must . . . inform

the defendant of . . . the mandatory minimum penalty provided by

law, if any, and the maximum possible penalty provided by law.

. . .” Fed. R. Crim. P. 11(c)(1). The district judge informed

Santo at the plea hearing that the mandatory minimum sentence

was five years. He did so on the basis of the information

provided in the plea agreement. The agreement stated that the

relevant Count One carried a mandatory minimum of five years.

It further stated that the “parties agree to take the position

in connection with the drug counts that Santo is accountable for

at least 100 grams of heroin . . . and the five year minimum

mandatory provision is applicable.” Slip op. *(3). Because it

had no information raising the possibility of a higher minimum

sentence, the court did what the rule required. 

The majority holds that “the court failed to comply

with the express provisions of Rule 11(c)(1) when it incorrectly

advised Santo as to the minimum penalties that applied in his

case.” Slip op. *(14). In considering that holding, it is

critical to appreciate what this case does and does not involve.
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This is not a case in which, at the time of the plea, the drug

quantity was undetermined, nor is this a case in which the judge

failed altogether to advise the defendant of the applicable

mandatory minimum. The “minimum penalties that applied in his

case” as of the time of the Rule 11 colloquy were those that

applied to the drug quantity on which defendant and the

government had agreed in the plea bargain that was before the

court when it took the plea. Slip op. *(3). That the Probation

Department subsequently increased the drug quantity attributed

to Santo, recommending a ten-year mandatory minimum, does not

retroactively infect what the district court did with error. 

The majority treats this as a case in which the drug

quantity attribution is not finally determined until after the

plea process is completed. Slip op. *(12). In such a case of

“lack of certainty,” the district court must inform the

defendant of the different mandatory maximums and minimums that

could apply. Slip op. *(13). The majority quotes from United

States v. Watch, 7 F.3d 422 (5th Cir. 1993), in which the court

said that “a prudent district judge hearing a plea from a

defendant charged under an indictment or information alleging a

§ 841(a) violation but containing no quantity allegation may

simply walk a defendant through the statutory minimum sentences

prescribed in § 841(b) explaining that a mandatory minimum may
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be applicable and that the sentence will be based on the

quantity of drugs [attributed to the defendant].” Id. at 429

(emphasis added). In the instant case, of course, the

government had informed the court at the plea hearing of the

quantity attributed to defendant. And the court’s statement in

Watch is dictum because the conviction was vacated on the ground

that the court did not inform defendant of any mandatory minimum

sentence. See id. at 428 n.5. Similarly, in United States v.

Herndon, 7 F.3d 55 (5th Cir. 1993), and United States v. Padilla,

23 F.3d 1220 (7th Cir. 1994), reiterating the Watch dictum, the

convictions were reversed because the court had failed to inform

the defendant of any applicable mandatory minimum sentence. See

Herndon, 7 F.3d at 56; Padilla, 23 F.3d at 1222 n.2.

But this is not such a case. Here, the drug quantities

attributed to Santo had been determined by the plea agreement.

A careful and reasonable district judge cannot be expected to

warn the defendant that the Probation Department might change

its mind later and report a larger drug quantity at sentencing.

What the district court does at the Rule 11 hearing must be

judged, not with the benefit of hindsight but by the state of

affairs at the time. To require the district court in a case

such as the one before us to inform a defendant of all the

different mandatory minimums and maximums not only is not
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required by Rule 11 but also would seem to confuse rather than

help the defendant. 

There is no authority for the proposition that the

district court’s failure to inform a defendant that a greater

quantity of drugs might be attributed to him at sentencing than

what the government had committed to in the plea agreement,

bringing into play higher mandatory minimums, constitutes

reversible error, nor can such a requirement be read into Rule

11(c)(1). 

Indeed, to require district judges to inform defendants

of all the different mandatory minimums will undermine the

purpose of Rule 11(c) to ensure defendants will make informed

decisions. It will also work to the prejudice of future

defendants (even if it helps Santo in this case). That is

because a defendant in Santo’s position, who entered a plea in

reliance on the plea agreement, would have a basis for moving to

withdraw his plea at sentencing if the PSR at that point

increased the drug quantity over what the government had

represented in the agreement--not because the court is bound by

the sentence contemplated by the agreement (which it is not

under Rule 11(e)(1)(C)) but because the government has

established the factual basis for the plea. If, on the other

hand, a defendant at the plea colloquy is told that
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notwithstanding the terms of his plea agreement, a greater

minimum sentence may apply than what the agreement provided for,

he has no ground for complaint if the PSR later states a drug

quantity exceeding that specified in the plea bargain.

(2) Assuming nonetheless that the district court erred,

the question is whether the error impaired Santo’s substantial

rights. The majority holds that “it is sufficiently likely that

Santo misjudged the consequences of his plea in light of the

court’s misinformation so that he must be allowed to withdraw

his plea.” Slip op. *(16). As noted above, the information

Santo received at the time of the plea was correct; it was only

by reason of a subsequent unforeseen development that the

factors controlling his sentence changed. In any event, United

States v. McDonald, 121 F.3d 7 (1st Cir. 1997), is

indistinguishable from the instant case. The court there held:

In the case at hand, the error did not impair the

appellant’s substantial rights. The court imposed a

sentence of 135 months– fifteen months longer than the

mandatory minimum–and calculated that sentence without

any reference to the mandatory minimum. It is,

therefore, readily apparent that because the guideline

sentencing range (at its nadir) outstripped the

mandatory minimum, the latter had no relevance to, and

no actual effect upon, the appellant’s sentence.

Consequently, the district court’s failure to apprise

the appellant of the mandatory minimum was an error

that did no discernible harm.

Id. at 11. So here, the district court performed the guideline

calculation without reference to the mandatory minimum, arriving
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at an offense level of 33 which, given Santo’s criminal history

category III, resulted in a guideline range of 168-210 months.

As in McDonald, the bottom of the range “outstripped” the tenyear mandatory minimum. 

The majority notes that at the plea hearing, the

government, in response to the court’s question, estimated a

sentencing guideline range that did not outstrip the ten-year

mandatory minimum. Slip op. *(18 n.5). McDonald does not

require reversal on those facts. McDonald is silent on whether

any sentencing guideline range was mentioned at the Rule 11 plea

colloquy; rather, it turned on the guideline range calculated by

the judge at sentencing with the aid of the parole officer’s PSR

recommendation, and that range exceeded the mandatory minimum.

McDonald holds that failure to inform the defendant of the

applicable mandatory minimum at the Rule 11 hearing does not

impair his substantial rights where that minimum was below the

applicable sentencing guideline range.

To sum up, Santo may have been unfairly treated when

he was ambushed by a revised PSR at the sentencing hearing. He

may well have been entitled to withdraw his plea had he asked.

That he failed to do so, however, does not make what the

district court did reversible error. 

For these reasons, I would affirm the judgment.
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