United States Court of Appeals
                            FOR THE EIGHTH CIRCUIT
                                   ___________

                                   No. 08-3598
                                   ___________

United States of America,
                                     *
           Plaintiff-Appellee,       *
                                     * Appeal from the United States
     v.                              * District Court for the Eastern
                                     * District of Missouri.
Edward L. Gray,                      *
                                     * [PUBLISHED]
           Defendant-Appellant.      *
                                ___________

                             Submitted: June 12, 2009
                                Filed: September 21, 2009
                                 ___________

Before BYE, HANSEN, and BENTON, Circuit Judges.
                           ___________

PER CURIAM.

      Edward Gray appeals his conviction, entered upon his plea of guilty, to a charge
of unlawful possession of a firearm by a convicted felon in violation of 18 U.S.C
§ 922(g)(1). He asserts the district court committed reversible error by failing to
inform him of the minimum and maximum sentences involved, as well as an
obligation of the court to calculate the applicable Sentencing Guideline range and to
consider it along with possible departures under the Sentencing Guidelines, and other
sentencing factors under 18 U.S.C § 3553(a). See Fed. R. Crim. P. 11(b)(1)(H),(I),
and (M). We reverse.
                                            I

       At the change-of-plea hearing, the district court asked Gray a series of questions
so as to ensure his plea of guilty was knowing, intelligent, and voluntary. The district
court then asked the Assistant United States Attorney ("AUSA") to advise Gray of the
charge and the range of punishment in the case. The AUSA informed Gray of the
range of punishment, stating:

      [A] maximum penalty provided by law is a term of imprisonment not to
      exceed ten years, a fine of not more than $250,000, or both. The Court
      may also impose a period of supervised release of not more than three
      years.

      In addition, however, pursuant to 18 U.S.C. § 924(e), if the defendant is
      determined to be an armed career criminal within the meaning of that
      provision, there is a possibility of a mandatory minimum sentence of 15
      years imprisonment.

At no time did the court or the AUSA – as required by Federal Rule of Criminal
Procedure 11 – inform Gray of the maximum sentence he could face if found to be an
armed career criminal under 18 U.S.C. § 924(e), which is life in prison, or of the
court’s obligation to calculate the applicable Sentencing Guidelines range and to
consider such range, possible departures under the Sentencing Guidelines, and other
sentencing factors under 18 U.S.C. § 3553(a).

       After Gray entered his plea of guilty, the United States Probation Office
prepared a Presentence Investigation Report ("PSI"), finding Gray was an armed
career criminal.




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      Gray filed pro se objections to the PSI. Relevant to this appeal, he stated:

      On the front page of the presentence report, under OFFENSE it lists my
      Count 1 as 924(e)(1) which enhances the sentence to 15 years to life,
      which is not what I was indicted under or pled guilty to. I was indicted
      under 924(a)(2). This is what is on my indictment, and what I pled
      guilty to. There is a significant difference in the punishment range
      between the two categories.

       At the sentencing hearing, Gray repeatedly informed the court he was not aware
of the sentencing range he faced if found to be an armed career criminal: "They told
me that my charge carried one to ten; what I was indicted under. And as we said, I
was pleading guilty to. That's what he told me."; "I never heard of this until the PSI
came. I didn't hear of that thing. He didn't talk to me about that. Through the whole
time I've been locked up ain't tell me nothing about 15 years; a career thing.";
"Because when he said the time, he say one to ten."

      The transcript reveals that, in response to Gray's objections, the district court
judge responded dismissively towards the defendant for even lodging his objections:

      THE COURT: What are you griping about now?

      THE DEFENDANT: I misunderstood. I am sorry sir.

      THE COURT: What are you griping now?

      THE DEFENDANT: I misunderstood it. I mean --

      THE COURT: No, no, no. When I asked you when you had your hand
      up swearing and said you understood. See, you have to give Caesar what
      is Caesar's, my man.

      THE DEFENDANT: Yes sir.


                                         -3-
THE COURT: Don't come in here with no wrong game with me. They
say, "That will not play in Peoria," big guy.

THE DEFENDANT: Yes, sir.

THE COURT: You told me. I'm the Jessie James around here.

THE DEFENDANT: Yes, sir. Yes, sir.

THE COURT: I told you what it was. Now you go up here talking some
other stuff.

THE DEFENDANT: Can I please just say one thing, sir?

THE COURT: You've about said enough.

THE DEFENDANT: Okay.

THE COURT: But let's hear it anyway. Give you another chance to say
something.

THE DEFENDANT: I probably just said it wrong. It came out wrong.
This is – I didn't understand the numbers. I was at St. Genevieve. I ain't
got no law books or nothing. I ain't know the 924.

THE COURT: I am not talking about all of that.

THE DEFENDANT: Oh, okay.

THE COURT: I am talking about when you were in here and the
Assistant United States Attorney told you what the charge was.

THE DEFENDANT: Yes.

THE COURT: Told you how much time was involved. And I asked:
"Did you understand?" You said, "Yes, sir."



                                   -4-
      THE DEFENDANT: Yes, sir. Yes, sir.

      THE COURT: Why you keep hollering about this then?

      THE DEFENDANT: Because when he said the time, he say "one to ten."

      THE COURT: Do you know who Jessie James is?

      THE DEFENDANT: Yes, sir.

      THE COURT: What am I just telling you? That I am up here with this
      robe, flag, and all this stupid stuff. Who is running this show?

      THE DEFENDANT: You is, sir.

      THE COURT: Please.

      THE DEFENDANT: You is, sir. Sorry.

      THE COURT: Why you run some stuff like that? You said you
      understood.

      THE DEFENDANT: I understand now.

      THE COURT: So give it up.

      THE DEFENDANT: Yes, sir. Yes, sir.

      THE COURT: That's why I might have to get out this two-by-four and
      hit you with it.

(Sent. Tr. pp. 6-9.)

      In sum, the district court overruled or implicitly overruled Gray's pro se
objections and later sentenced Gray to fifteen years' imprisonment. This timely appeal
followed.

                                         -5-
                                           II

       Gray alleges the district court violated Federal Rule of Criminal Procedure 11.
Rule 11 requires the district court to follow certain protocol to ensure a defendant's
plea is knowing, intelligent, and voluntary. Relevant here, Rule 11(b)(1)(H) requires
the court to inform the defendant of the maximum possible penalty; subsection
(b)(1)(I) requires the court to inform the defendant of the minimum penalty; and
subsection (b)(1)(M) requires the court to inform the defendant of the district court's
obligation to calculate the applicable sentencing guideline range and to consider that
range, possible departures under the Sentencing Guidelines, and other sentencing
factors under 18 U.S.C § 3553(a).

        When considering an alleged Rule 11 error, this Court must first determine if
the defendant objected before the district court. If so, we review for harmless error,
and the government has the burden of proving the defendant's knowledge and
comprehension of the omitted information would not have been likely to affect his
willingness to plead guilty. United States v. Gillen, 

, 903 (8th Cir. 2006).
If not, we review for plain error, and the burden is on the defendant to show he would
have plead not guilty but for the Rule 11 violation. United States v. Dominguez
Benitez, 

, 83 (2004). We liberally construe pro se objections to determine
whether the defendant objected. Haines v. Kerner, 

, 520-21 (1972);
Hudson v. Gammon, 

, 786 (8th Cir. 1995); see also United States v.
Johnson, 

(8th Cir. 2005) (unpublished); Atkinson v. Bohn, 

(8th Cir. 1996).

      Liberally construing Gray's pro se objections to the PSI and his complaints at
the sentencing hearing, we find Gray repeatedly attempted to object that he did not
understand by pleading guilty he could be subject to a 15-year mandatory minimum
sentence or a maximum sentence of life in prison. In his objections, Gray claimed he

                                          -6-
was only indicted under, and pled guilty to, § 924(a)(2), which carries a sentencing
range of one-to-ten years, and that he never pleaded guilty to § 924(e)(1), which
carries a fifteen-to-life sentencing range. At his sentencing hearing, Gray told the
court he did not learn of the possible sentencing under § 924(e)(1) until he received
the PSI, and he repeatedly stated his belief he was only pleading guilty to an offense
which carried a one-to-ten year sentence. Liberally construed, these pro se arguments
should be read as Gray objecting to the court’s failure to inform him of the minimum
and maximum sentences he faced, which are clear violations of Rule 11. Because
Gray timely objected to the alleged Rule 11 violations in district court, this Court
reviews for harmless error. See United States v. Vonn, 

, 59 (2002).

       Gray alleges the district court violated Rule 11 by failing to inform him of (1)
the mandatory minimum sentence he could face; (2) the maximum sentence he could
face; and (3) the district court's obligation to calculate the applicable Sentencing
Guideline range and to consider that range, possible departures under the Sentencing
Guidelines, and other sentencing factors under 18 U.S.C. § 3553(a).

      Rule 11(b)(1)(II) requires the district court to inform Gray of the minimum and
maximum sentence he could face after pleading guilty. With respect to the minimum
penalty, the advice given to the defendant by the AUSA (upon whom the district court
judge relied to fulfill in part what is the court's duty under Rule 11) is as follows:

      The defendant is charged with being a felon in possession of a firearm
      under 18 U.S.C. 922(g). And the statute provides penalties – a
      maximum penalty provided by law is a term of imprisonment not to
      exceed ten years, a fine of not more than $250,000, or both. The Court
      may also impose a period of supervised release of not more than three
      years.

      In addition, however, pursuant to 18 U.S.C. § 924(e), if the defendant is
      determined to be an armed career criminal within the meaning of that


                                         -7-
      provision, there is a possibility of a mandatory minimum sentence of 15
      years imprisonment. (emphasis supplied).

         We have previously held there is "substantial compliance" with Rule 11 when
a prosecuting attorney informs the defendant of the possible sentence he faces, and the
court extensively questions the defendant to make sure the plea is knowing,
intelligent, and voluntary. United States v. Lambros, 

, 956-66 (8th Cir.
1976). However, the AUSA must do so accurately. The double conditional language
(if . . . [then] . . . a possibility) utilized by the AUSA was in error. If a defendant is
determined to be an armed career criminal pursuant to § 924(e), a 15-year minimum
sentence is mandatory, not just a mere "possibility." The prosecutor's language
substantially diminished and downplayed the seriousness of the actual situation the
defendant faced and did little to alert him to a very real, direct, and substantial
consequence of his plea.

       With respect to Gray's maximum penalty, neither the district court nor the
prosecutor informed Gray of the maximum sentence he faced – life in prison – should
he be found to be an armed career criminal. Thus, because the district court erred in
failing to inform Gray of either the minimum or maximum penalty he faced, we must
determine whether the error was harmless.

      In this context, the government must demonstrate Gray's knowledge and
comprehension of the maximum sentence would not have affected his willingness to
plead guilty. 

.1 Most cases in which Rule 11 violations were
found to be harmless involve situations where the defendant was aware, or could have
been made aware, of the omitted information through other means, e.g., a plea


      1
       The district court also violated Fed. R. Crim. P. 11(b)(1)(M) by failing to
inform Gray of its obligations concerning the Sentencing Guidelines; however, Gray
never complained about this violation, and there is no evidence Gray would have
proceeded differently had the district court complied with this subsection of Rule 11.

                                           -8-
agreement containing the information the court omitted during the plea hearing. See

United States v. McCarthy, 

, 1575-76 (8th Cir. 1996);
United States v. Young, 

, 1062 (8th Cir. 1991). In this case, however,
there was no plea agreement, nor any evidence demonstrating Gray ever knew or
should have known that by pleading guilty his range of punishment could include life
in prison. In contrast, Gray’s repeated objections indicate he was unaware of the
enhanced sentencing range he faced. Furthermore, his desire to vacate the plea, even
after having received the statutory minimum, indicates he would have likely
proceeded to trial rather than be subject to the increased sentencing range he faced as
an armed career criminal. Thus, the government cannot meet its burden of
demonstrating Gray’s knowledge and comprehension of the maximum sentence he
faced – life in prison – would not have affected his willingness to plead guilty.

       In support of its argument for harmless error, the government points out Gray
was sentenced to fifteen years' imprisonment, which is within the possible sentencing
range to which he was informed by the court. Support for this argument can be found
in the advisory committee notes to Rule 11, which provide as a possible example of
harmless error a situation where "the judge understated the maximum penalty
somewhat, but the penalty actually imposed did not exceed that indicated in the
warnings." Fed. R. Crim. P. 11(h) Advisory Committee's notes (1983 amendment);
see also United States v. Raineri, 

(1st Cir. 1994) (holding that error in
understating maximum possible sentence was harmless because defendant was
sentenced to a lesser sentence within the range of which he was made aware).

       The government’s argument fails, however, because the test for harmless error
is whether the defendant's knowledge and comprehension of the omitted information
would likely have affected his willingness to plead guilty. 

.
Thus, the question is not whether Gray was sentenced within the range of which the
court did make him aware; rather, the question is, had Gray known of the full range
to which he could be sentenced, would he have pled guilty in the first place. When

                                         -9-
a district judge simply understates a maximum penalty by a relatively small amount
and a defendant is sentenced within that range, it is possible, maybe even probable,
the slight understatement of the maximum sentence did not affect the defendant’s
decision to plead guilty. In this case, however, the "judge did not understate the
maximum penalty; rather, []he omitted mention of any maximum penalty." United
States v. Jaramillo-Suarez, 

, 1372 (9th Cir. 1988) (holding the district
court's failure to inform the defendant he could face a maximum of twenty years in
prison was not harmless error, even though he was sentenced to the mandatory
minimum, of which he was made aware). A complete failure to inform Gray of the
maximum sentence is far different from the type of trivial understatement of a
maximum sentence identified as harmless in the advisory committee’s notes to Rule
11. Given the complete failure to inform Gray he could be sentenced up to life in
prison should he be found to be an armed career criminal, as well as Gray’s vociferous
complaints upon learning the same, we cannot say with certainty that had Gray known
of the accurate range of imprisonment he faced by pleading guilty, he would have pled
guilty anyway.

        The second argument which can be made in support of finding harmless error
is a single statement Gray made during his sentencing hearing in which he said, "I'm
not saying – I'm pleading guilty. I am responsible for what I done." Although this
could be interpreted as a re-affirmation of his desire to plead guilty even after having
learned of the true sentencing range, the tenor of the sentencing hearing belies such
an assumption. Far from an unequivocal assertion of Gray's desire to plead guilty, this
statement more likely indicates a defensive reaction to the district court's brusque
treatment of his legitimate objections. Our result would likely be different had the
district court recognized its Rule 11 violation and inquired of Gray, after a moment
of reflection in light of the new information, whether he still wished to proceed with
his guilty plea. Instead, the district court repeatedly maintained inaccurately (at least
with respect to the maximum sentence) that Gray had been told of the possible
sentencing range he faced, and it responded to his complaints with disdainful and

                                          -10-
combative language. Thus, Gray's statement was more likely a defensive reaction to
the district court's intimidation than a reasoned and fully informed statement of his
desire to plead guilty having now learned of the maximum sentence he faced.
Therefore, we are unconvinced this statement, standing alone, satisfies the
government's high burden of proving Gray's knowledge and comprehension of the
maximum sentence he faced would not have affected his decision to plead guilty.

                                         III

      Accordingly, we vacate Gray’s conviction and remand for further proceedings
consistent with this opinion.
                        ______________________________




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