United States Court of Appeals
                             FOR THE EIGHTH CIRCUIT
                                    ___________

                                    No. 08-3881
                                    ___________

United States of America,                *
                                         *
             Appellee,                   *
                                         * Appeal from the United States
      v.                                 * District Court for the
                                         * Eastern District of Missouri.
Joseph Martin, Jr.,                      *
                                         *
             Appellant.                  *
                                    ___________

                              Submitted: September 25, 2009
                                 Filed: October 19, 2009
                                  ___________

Before LOKEN, Chief Judge, WOLLMAN, and SHEPHERD, Circuit Judges.
                             ___________

WOLLMAN, Circuit Judge.

       Joseph Martin Jr. pleaded guilty to two counts of manufacturing, distributing
or possessing with intent to manufacture or distribute a controlled substance, in
violation of 21 U.S.C. § 841(a)(1). The district court1 sentenced Martin to 160
months’ imprisonment, to be followed by five years of supervised release. Martin
appeals from his sentence, arguing: (1) the district court erred in determining that he
was responsible for manufacturing cocaine base, rather than merely for the
distribution of cocaine powder; (2) he should have been sentenced below the


      1
        The Honorable Donald J. Stohr, United States District Judge for the Eastern
District of Missouri.
guidelines range because of sentencing entrapment; and (3) the government breached
the plea agreement by failing to recommend an acceptance of responsibility reduction
and by encouraging an obstruction of justice enhancement. We affirm.

                                    I. Background

      In exchange for Martin’s plea, the government agreed to recommend that the
sentencing court grant a three-level reduction in the offense level for acceptance of
responsibility and avoidance of trial pursuant to U.S. Sentencing Guidelines §§
3E1.1(a) & (b).

       The facts set forth in the plea agreement were that a cooperating individual (CI)
contacted Martin in November 2006 about purchasing crack. Martin agreed to arrange
a purchase of powder cocaine from a third party, and Martin offered to cook the
powder cocaine into crack for a separate fee. The CI gave $1700 to Martin for the
purchase and $700 for converting the cocaine into crack. Together they purchased
approximately two ounces of powder cocaine. After the purchase, Martin gave the
powder cocaine to the CI. Martin and the CI then drove in separate cars to Martin’s
residence, where the CI returned the powder cocaine to Martin. Martin then cooked
the powder cocaine into crack, using a coffee cup, baking soda, and microwave oven.
After the cooking was finished, Martin gave the crack to the CI. The finished product
was determined to consist of 53.8 grams of crack.

       In December 2006, the CI again contacted Martin about purchasing crack and
a similar train of events ensued, with the CI providing $2550 to Martin for the
purchase of cocaine and $900 for converting it into crack. As in the first transaction,
Martin gave the powder cocaine to the CI following the purchase, whereupon the two
then traveled in separate cars to Martin’s residence, where the CI gave the powder
cocaine back to Martin. Using the same technique, Martin cooked the crack and then
gave it to the CI. The transaction involved 36.87 grams of crack.

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       The plea agreement included a number of caveats. The government reserved
the right to balk on recommending an acceptance of responsibility reduction if new
information “inconsistent with the defendant’s acceptance of responsibility” came to
light. The agreement also specified that “any actions of the defendant which occur or
which become known to the government subsequent to this agreement and are
inconsistent with the defendant’s acceptance of responsibility including, but not
limited to criminal conduct, are grounds for loss of acceptance of responsibility.” It
also stated that Sentencing Guidelines (guidelines) issues not explicitly mentioned in
the agreement, but referenced in the Presentence Investigative Report (PSR), “may be
presented to the Court for consideration.” The agreement specified that post-plea
criminal conduct by the defendant would release the government from “any
obligations or limits on its power to prosecute the defendant,” and that any such
conduct would be grounds for loss of the acceptance of responsibility reduction. It
also stated that the sentencing court was not bound to follow the government’s
recommendations and that the sentencing court’s refusal to follow these
recommendations was not grounds for withdrawal of the plea. The plea agreement
specifically noted that the parties disagreed about when the transactions were
completed, and the parties anticipated arguing this matter before the sentencing court.

       After entering into the plea agreement, Martin remained in custody of the
United States Marshal at the St. Louis County Justice Center, during which time he
made a number of statements from jail that were recorded by jail officials and
analyzed by the FBI. In these statements, Martin denied responsibility for the crimes
alleged, threatened to physically harm his girlfriend and the government agents
involved in the case, and discouraged witnesses from cooperating with government
investigators. Martin also violated jail visitation policy by arranging visits with
prohibited visitors.

     Based on these statements and actions, Probation and Pretrial Services
submitted a PSR that did not recommend a reduction for acceptance of responsibility

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and instead recommended adding two offense levels for obstruction of justice.
Because the obstruction of justice occurred while Martin was incarcerated, the PSR
recommended adding two points to his criminal history pursuant to U.S.S.G. §
4A1.1(d). These additional two points raised Martin from a category I to a category
II offender. The PSR further recommended that the district court find that crack,
rather than powder cocaine, should determine the base offense level. According to the
PSR, Martin’s offense level should have been 32, criminal history category II, for a
guideline range of 135 to 168 months’ imprisonment. If the substance in question had
been powder cocaine and if Martin had received the acceptance of responsibility
reduction and no obstruction of justice enhancement, then his offense level would
have been 13, criminal history category I, with a guideline range of 12-18 months’
imprisonment.

       Martin filed multiple objections to the PSR. He argued, first, that the sentence
should be based upon the guidelines for cocaine powder because the transaction ended
when the CI took possession of the cocaine powder. Second, Martin argued that his
statements from jail were not general denials of responsibility for the crimes alleged,
but rather specific denials of responsibility for distributing crack. Thus, an acceptance
of responsibility reduction was still warranted. Third, Martin argued because his
telephone conversations were not actual attempts to obstruct justice but rather
expressions of frustration about his prosecution and detention, an obstruction of
justice enhancement was unjustified.

       After a lengthy sentencing hearing with multiple witnesses, the district court
determined that Martin should be sentenced for manufacturing 90.67 grams of crack
and that Martin’s post-plea conduct warranted a two-level enhancement for
obstruction of justice rather than a reduction for acceptance of responsibility. The
district court then sentenced Martin as set forth above.




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                                     II. Analysis

                          A. Powder/Crack Identification

       Martin argues that the district court should have sentenced him according to the
guidelines range for cocaine powder rather than crack because the transaction ended
when the powder cocaine was delivered to the CI, rather than after delivery of the
crack. Identification of controlled substances is a factual finding reviewed for clear
error, and we will reverse only when we are definitely and firmly convinced that the
district court was mistaken. United States v. Whitehead, 

, 1071 (8th
Cir. 2007).

       As outlined above, Martin arranged on two separate occasions for the purchase
of powder cocaine on behalf of the CI, distributed powder cocaine to the CI, took the
same powder cocaine from the CI, converted the powder cocaine into crack, and gave
crack to the CI. On both occasions, Martin solicited and received a separate fee from
the CI for manufacturing crack.

       Like the district court, we find Martin’s argument unconvincing. In the plea
agreement, Martin admitted facilitating the purchase of the powder cocaine for the
purpose of manufacturing crack. The parties disagreed as to whether the transactions
were completed when the CI took possession of the powder cocaine or when Martin
handed the crack to the CI. The district court considered extensive testimony on this
topic. Its conclusion that the transaction did not end until the crack was delivered is
well supported by the evidence, and thus we are not firmly and definitely convinced
the district court was mistaken.




                                         -5-
                              B. Powder/Crack Disparity

       Martin argues that the district court erred in not granting him a departure based
upon the disparity between cocaine powder and crack sentences. We review the
district court’s application of the guidelines de novo and review factual findings for
clear error. United States v. Mathijssen, 

, 498 (8th Cir. 2005). Because
this objection was not raised below, we review it under plain error analysis. United
States v. Davis, 

, 917 (8th Cir. 2008).

       Martin relies upon Davis for the proposition that although a district court need
not deviate from the guidelines due to the powder/crack disparity, a court errs when
sentencing if it does not believe that it can deviate from the guidelines. 

that the district court’s failure to refer to its ability to depart from the guidelines
proves that the district court was under the false belief that it had no discretion to grant
a downward departure. The absence of any explicit statement is not surprising, given
that this objection was not raised before the district court. Davis holds that a district
court errs when it denies its ability to grant a downward departure, and imposes a
sentence predicated upon that false belief. 

case, there is no evidence that
the court was under a mistaken impression about its discretionary power. Indeed, the
court considered a PSR that specifically noted the court’s discretion in this regard.
Martin’s extensive dealing with controlled substances and previous crimes were
adequate grounds for not granting a downward departure based on the powder/crack
disparity. Thus, the district court did not plainly err in failing to grant Martin a
downward departure on these grounds.

                               C. Sentencing Entrapment

      Martin argues that the government’s use of sentencing entrapment justifies a
sentence below the guidelines range. Sentencing entrapment occurs when official
conduct leads an individual otherwise indisposed to dealing in a larger quantity or

                                            -6-
different type of controlled substance to do so, and the result is a higher sentence.
United States v. Searcy, 

, 1099 (8th Cir. 2000). When considering a
claim of sentencing entrapment, the locus of inquiry is the defendant’s predisposition.

The defendant bears the burden to prove by a preponderance of
evidence that he lacked the predisposition to sell a larger quantity or different type of
drug. United States v. Searcy, 

, 942 (8th Cir. 2002). The court considers
the government’s conduct only to show inducement. 

. The
government’s conduct is not determinative, and the central question throughout the
analysis of a sentencing entrapment claim is whether the defendant was predisposed
to sell a larger quantity or a different type of drug. 

Sentencing
entrapment is a factual finding that we review for clear error. United States v. Ruiz,

, 776 (8th Cir. 2006).

       In Searcy, we found that sentencing entrapment could have occurred when a
defendant, who had “never dealt crack,” was coaxed to do so by a government

. In this case, Martin had sold the CI smaller quantities
of crack on previous occasions. In response to the CI’s request that Martin facilitate
the purchase of larger quantities of crack from a third party, Martin proposed to
arrange a larger purchase of cocaine powder and offered to manufacture the crack for
a separate fee. Martin devised this plan on his own, and he executed it without
government coercion. There is no evidence that Martin was indisposed to this course
of events. Assuming the claim of sentencing entrapment was properly raised at
sentencing (a question about which we have some doubt), the district court’s failure
to find sentencing entrapment was not clearly erroneous.

                          D. Breach of the Plea Agreement

      Finally, Martin contends that the government breached the plea agreement by
arguing against the acceptance of responsibility reduction and in favor of the
obstruction of justice enhancement. “We review de novo issues pertaining to the

                                          -7-
interpretation and enforcement of a plea agreement. Plea agreements are contractual
in nature and should be interpreted according to general contractual principles.”
United States v. Thompson, 

, 1039 (8th Cir. 2005) (citations omitted).
If a defendant believes the government has breached a plea agreement, he must object
to preserve the issue for appeal. Puckett v. United States, 

, 1428
(2009). A defendant who fails to object properly is precluded from raising the matter
on appeal. 

This general rule, however, is subject to a narrow exception:
“A plain error that affects substantive rights may be considered even though it was not
brought to the court’s attention.” Fed. R. Crim. P. 52(b). Plain-error review under
Rule 52(b) involves four aspects: (1) the defendant must not affirmatively waive the
error; (2) the error must be clear or obvious; (3) the error must affect the defendant’s
substantive rights, which usually means the defendant must show the outcome would
have been different had the error not been committed; and (4) the court of appeals
must decide whether to exercise its discretion in remedying the error, a discretion to
be reserved for those cases that undermine the fairness, integrity, or public reputation
of judicial proceedings. 

.

       Martin maintains that he preserved his objection by arguing that the district
court should have held the government to the terms of the plea agreement. As the
government points out, however, Martin did not argue that the government breached
the plea agreement, or that he should have been allowed to rescind his plea at
sentencing given the government’s supposed breach. Martin solely argued that his
post-plea conduct did not justify an obstruction of justice enhancement and loss of the
acceptance of responsibility reduction. Thus, having not been properly preserved for
appeal, we review the claim of breach for plain error. 

      It is neither clear nor obvious that the government breached the plea agreement.
The agreement stated that the government could refrain from recommending an
acceptance of responsibility reduction if new information came to light after the plea
and before sentencing. The agreement also released the government from its

                                          -8-
responsibilities if Martin engaged in post-plea criminal conduct. Martin’s statements
from jail and violations of jail rules triggered both of these provisions, which allowed
the government to refrain from recommending an acceptance of responsibility
reduction. Further, the plea agreement also stated that guidelines issues not mentioned
in the agreement but raised by the PSR could be presented to the court for
consideration. The PSR recommended an obstruction of justice enhancement, Martin
opposed the enhancement, and the government responded. The government did not
initiate the obstruction of justice enhancement, arguing in favor only after it was
already before the court. Thus, there was no breach of the agreement. Even if we
found a breach by the government, Martin would have to show that the court would
have acted differently had there been no breach. No such proof has been offered, and
thus no plain error occurred.

                                         III.

      The judgment is affirmed.

                        ______________________________




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