In the
 United States Court of Appeals
               For the Seventh Circuit
                          ____________

No. 05-1673
UNITED STATES OF AMERICA,
                                                 Plaintiff-Appellee,
                                 v.

JULIAN SALAZAR,
                                            Defendant-Appellant.
                          ____________
            Appeal from the United States District Court
       for the Northern District of Illinois, Eastern Division.
              No. 03 CR 88—James B. Zagel, Judge.
                          ____________
       ARGUED MAY 2, 2006—DECIDED JULY 13, 2006
                     ____________


  Before CUDAHY, RIPPLE, AND WOOD, Circuit Judges.
  CUDAHY, Circuit Judge. Julian Salazar, a leader of the
Insane Deuces street gang, pleaded guilty to one count
of possessing a firearm, which, as a felon, he may not do. 18
U.S.C. § 922(g). In exchange for his plea, the government
agreed to recommend a sentence at the low end of the
applicable range of the federal Sentencing Guidelines,
provided that the district court accepted its calculated
range of 108 to 120 months’ imprisonment. Salazar argues
that the government, in addressing the court, breached that
agreement by paying only lip service to its recommendation
while characterizing him as a cold-blooded killer willing to
do anything to protect the gang. We disagree with Salazar
and affirm the judgment of the district court.
2                                               No. 05-1673

  The Insane Deuces street gang operates primarily in
northern Illinois. In 2002, Salazar and other gang leaders
grew suspicious that John Landeros, a gang member who
had been caught with four ounces of cocaine but never
charged, was a government informant. On September 15,
2002, Salazar and two other gang leaders arrived at
another gang member’s house to discuss the situation.
Salazar ultimately ordered this gang member to make
arrangements to kill Landeros. As it happened, however,
Landeros was not working for the government, but—irony
of ironies—the member Salazar ordered to kill Landeros
was.
  As directed, the government informant made preliminary
arrangements to kill Landeros and wore a recording device
during planning meetings with Salazar. At one meeting
(where the recording device failed to work), Salazar in-
structed the informant to contact him before killing
Landeros so that Salazar could obtain cocaine from the
intended victim without paying for it. At a later meeting
that was recorded, Salazar told the informant not to worry
about killing Landeros because that was Salazar’s “head-
ache” as a leader of the gang. They also discussed whether
a .22 caliber pistol would be adequate to kill Landeros.
Shortly after this conversation, police arrested Salazar.
   A grand jury indicted Salazar on one count of distributing
cocaine and one count of being a felon in possession of a
firearm. On June 21, 2004, he entered a blind guilty plea on
the firearm charge. The government then agreed to drop the
cocaine charge, but the parties could not agree on the
Guidelines calculation. The government agreed that if the
district court accepted its Guidelines calculation, it would
seek a sentence at the low end of the Guidelines range.
After applying enhancers for conspiracy or solicitation to
commit murder and for being the organizer or leader of a
criminal activity, the government concluded that the
appropriate range fell between 108 and 120 months.
No. 05-1673                                                  3

  At the sentencing hearing, the government stated:
    The Government, pursuant to the agreement reached
    with defense counsel and the defendant’s plea agree-
    ment as has been previously noted to the Court, would
    recommend that the defendant be sentenced at the
    low end of that Guideline range, one hundred eight to
    one hundred twenty. That is an appropriate sentence in
    this case, your Honor. This is a cold-blooded killer who
    hires others to go out and kill fellow gang members
    when he thinks they are cooperating with the police.
    When he thinks his way of life, the gang life, is in
    jeopardy. That is the tapes, the tapes make that very,
    very clear. He casually discusses it without even
    blinking an eye. That is an appropriate sentence in this
    case and we urge that you sentence him accordingly.
(R., Sentencing Hr’g 100, Feb. 9, 2005.) The district court
accepted the government’s presentation but sentenced
Salazar to 120 months—the statutory maximum for the
firearms charge. Salazar argues that the government
breached its plea agreement; his theory is that, in describ-
ing him as a cold-blooded killer, the government effectively
urged a higher sentence while paying lip service to the
agreed plea.
  Salazar argues for the first time on appeal that the
government breached its plea agreement. We accordingly
review the district court’s judgment for plain error. United
States v. Matchopatow, 

, 851 (7th Cir. 2001);
United States v. D’Iguillont, 

, 614 (7th Cir.
1992). This standard is remarkably demanding; in order
to prevail, Salazar must show: (1) that there was error; (2)
that the error was plain or obvious; (3) that the error
affected his substantial rights; and (4) that the error
seriously affects the fairness, integrity, or public reputation
of judicial proceedings. United States v. Olano, 

, 734-36 (1993); United States v. Sharp, 

,
4                                                No. 05-1673

734 (7th Cir. 2006). In the context of an arguably breached
plea agreement, Salazar must show that but for the breach,
his sentence would have been different. D’Iguillont, 

.
  The first step of our analysis is to consider whether the
government did in fact breach its plea agreement with
Salazar. Since plea agreements are contracts, their con-
tent and meaning are determined according to ordinary
contract principles. United States v. Ingram, 

,
1184 (7th Cir. 1992). A substantial breach is required before
the government is considered in breach of its plea agree-
ment. United States v. Hauptman, 

, 51-52 (7th
Cir. 1997).
  It is well settled that the government must fulfill any
promises it makes in exchange for a defendant’s guilty plea.
Santobello v. New York, 

, 262 (1971);

. The terms of these promises,
however, will be read according to their natural meaning.
United States v. Williams, 

, 992 (7th Cir. 1999).
Salazar argues that the government failed to fulfill its
promises by only nominally honoring the terms of the
agreement while simultaneously making arguments that
substantially undercut its sentencing recommendation—all
in an attempt to induce the judge to impose a sentence
longer than the one agreed to.
  We have not earlier had the opportunity to consider the
status of a plea agreement in a case like this one. Other
circuits faced with similar circumstances have concluded
that undercutting a sentencing recommendation may rise to
the level of a breach of an agreement. See, e.g., United
States v. Vaval, 

, 152-54 (2d Cir. 2005) (con-
cluding that the government breached its plea agreement
when it set forth an argument justifying an upward depar-
ture despite provisions prohibiting it from doing so); United
States v. Gonczy, 

, 53-54 (1st Cir. 2004) (conclud-
No. 05-1673                                                 5

ing that the government breached its plea agreement when
it argued for the agreed-upon term but then noted that “the
defendant at a minimum deserves what the Guidelines
provide for and those are his just deserts”); United States v.
Saling, 

, 765-67 (5th Cir. 2000) (concluding
that the government breached its plea agreement when an
attorney other than the one who negotiated the plea stated
that she “just encourage[s] the Court to consider those
factors when the Court determines whether this should be
a concurrent or consecutive sentence” when the government
had agreed not to oppose concurrent sentences).
  These conclusions were, we think, quite reasonable. Plea
agreements only work when both sides adhere to their
promises. Although the court of appeals is generally
hesitant to micromanage the sentencing process, it is
especially important that the government recognize its
obligations with respect to guilty pleas. See, e.g., 

. Permitting the government to perform
by half-heartedly requesting a light sentence while simulta-
neously arguing forcefully that a defendant is vicious—and
failing to explain that its sentencing recommendation is
consistent with its characterization of him—does not serve
the broader purposes behind plea agreements (such as fair-
ness and efficiency).
   Salazar’s case is close—closer than some decided in the
other circuits. It is troubling that it is not wholly irra-
tional to interpret the government’s statements as mere
lip service to the terms of the agreement. While the govern-
ment does have an obligation under 18 U.S.C. § 3661 to
bring all information relevant to sentencing to the district
court’s attention, the statement at issue here could easily be
interpreted as contradicting the specific sentencing recom-
mendation. In some circumstances, it may be appropriate to
suggest a lighter sentence for a “cold-blooded killer.” But
since such a recommendation generally seems an anomaly,
6                                                  No. 05-1673

some explanation is in order. However, the simple fact here
is that the government did in fact request that the district
court impose a low-end Guidelines sentence and noted its
obligation to do so more than once during the sentencing
hearing. (R., Sentencing Hr’g 93, 100, Feb. 9, 2005.)
  Additionally, although it characterized Salazar as a less-
than-upstanding citizen, the government did not request a
higher sentence or remind the judge that he need not abide
by the agreement. In fact, the government consistently
commented that the low-end Guidelines sentence was
appropriate. The facts here are close enough to conclude
that the government did not substantially violate the terms
of its agreement. Our conclusion must be that the govern-
ment honored its agreement with Salazar.
  Even if the government had breached the plea agreement,
however, Salazar still cannot overcome the requirements of
plain-error review. Reversal on the basis of plain-error
review is justifiable “only when the reviewing court is
convinced that it is necessary in order to avert an actual
miscarriage of justice.” 

. A
defendant wishing to establish plain error must show that
“but for the breach of the plea agreement his sentence
would have been different.” Id.1 Salazar is unable to point to
anything that persuasively suggests that the district court
would have imposed a different sentence but for the govern-
ment’s argument that he is cold-blooded. The district court
noted that it was disturbed by Salazar, a man who seemed


1
  Salazar argues that a D’Iguillont-type approach is appropriate
only where the district court did not follow the government’s
sentencing recommendation that arguably breached a plea
agreement. This argument is unduly narrow; the Court made no
suggestion of this type of limitation in the case. The opinion
merely states that “[n]othing in the record indicates that the
government’s objection caused a different outcome at his sentenc-
ing 

.
No. 05-1673                                                          7

to have delusions about his abilities and about his power.
(R., Sentencing Hr’g 102, Feb. 9, 2005.)2 And the judge
further made statements indicating that he would have
departed upwards even if the Guidelines had limited his
sentencing discretion in the case before him. (R., Sentencing
Hr’g 102, Feb. 9, 2005.) Nothing suggests that the district
court would have imposed a lower sentence if the govern-
ment had abided less ambiguously by the plea agreement in
the manner Salazar wished.
    Accordingly, we AFFIRM the judgment of the district court.




2
  At the conclusion of the sentencing hearing, the district court
judge stated:
      The thing that I find most distressing about the facts of this
      case and the character of the defendant is not the facts of
      what he did, which are bad enough, but the character and
      disposition he showed in the tapes. Mr. Salazar belongs to . . .
      a uniquely dangerous class of individuals; who . . . decide that
      their profession is to be the mastermind of a criminal
      enterprise—to give orders, to expect them to be obeyed, to
      determine life and death. . . . This is a man, I think, who had
      delusions about his power, about his control and about his
      abilities; none of which, if you are in a lawful enterprise, with
      bear lethal consequences. But in the field he chose, they do.
      I think it will take him a lot of time to understand just what
      his limitations are.
(R., Sentencing Hr’g 102, Feb. 9, 2005.)
8                                         No. 05-1673

A true Copy:
      Teste:

                    ________________________________
                    Clerk of the United States Court of
                      Appeals for the Seventh Circuit




               USCA-02-C-0072—7-13-06