Hilario Santos v. United States of America

United States Court of Appeals
For the Seventh Circuit
Chicago, Illinois 60604
Argued October 16, 2008
Decided November 12, 2008
Before
KENNETH F. RIPPLE, Circuit Judge
TERENCE T. EVANS, Circuit Judge
JOHN DANIEL TINDER, Circuit Judge
No. 08‐1048
HILARIO SANTOS,
Petitioner‐Appellant,
v.
UNITED STATES OF AMERICA,
Respondent‐Appellee.
Appeal from the United States District
Court for the Northern District of
Illinois, Eastern Division.
No. 06 C 4822
Matthew F. Kennelly, Judge.
O R D E R
After receiving a tip from a participant in a cross‐country drug deal, authorities
arrested all three participants, including Hilario Santos. Santos eventually pleaded
guilty to possessing cocaine and marijuana with the intent to distribute and was given a
10‐year sentence, the mandatory minimum. See 21 U.S.C. § 841(a)(1), (b)(1)(A). We
dismissed Santos’s direct appeal and he then sought postconviction relief under 28
U.S.C. § 2255, claiming that his trial counsel was constitutionally ineffective. According
to Santos, counsel did not sufficiently investigate the tipster and, consequently,
recommended pleading guilty rather than going to trial and pressing an entrapment
NONPRECEDENTIAL DISPOSITION
To be cited only in accordance with
Fed. R. App. P. 32.1

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defense. The district court rejected this argument, holding that Santos had no chance at
making a successful entrapment defense. Thus, the court denied Santos’s § 2255
motion, but it issued a certificate of appealability.
As early as June 2003, DEA agents believed that Santos and Martin Moreno were
involved in transporting drugs to Chicago. They monitored Moreno’s movements, even
placing a tracking device on the truck he owned, but did not take significant action until
December 2003 when Moreno contacted the authorities and reported that he was en
route to Chicago from Los Angeles in a truck containing 11 kilograms of cocaine and 50
pounds of marijuana. Moreno explained that Santos, who was making the trip by
plane, was the source of the drugs and intended to sell them to a buyer unknown to
Moreno. Moreno met with DEA agents who equipped him with a hidden audio
recorder and told him to go through with the drug deal. After Santos’s plane landed,
Moreno picked him up at Midway Airport and drove him to the meeting with the
buyer, William Robinson. DEA agents moved in and arrested all three men after
watching Santos transfer seven kilograms of cocaine from Moreno’s truck to Robinson’s
car. Santos and Robinson were indicted together, and both pleaded guilty. Moreno, by
contrast, was released shortly after the arrests. He was never charged with a crime, and
the government eventually lost track of him.
After pleading guilty, Santos filed a notice of appeal, but we granted appellate
counsel’s motion to withdraw and dismissed the appeal. United States v. Santos, 189
Fed. App’x 534 (7th Cir. 2006). Santos then filed his pro se motion under § 2255,
claiming four overlapping grounds for ineffective assistance of counsel, but on appeal
he discusses only the claim that counsel did not sufficiently investigate a potential
entrapment defense. The district court ordered the government to respond to Santos’s
motion, but the government did not. In response, the court appointed counsel and
ordered an evidentiary hearing. The court explained that it had adopted this practice in
response to the government’s repeated failures to answer § 2255 petitions after being
ordered to do so. (At oral argument, counsel for the government assured us that it was
not intentionally thumbing its nose at Judge Kennelly but that the failure to respond
was due to administrative snafus. The government also assured us that those problems
were now resolved.)
The district court limited the scope of the evidentiary hearing to the question of
whether Santos’s trial lawyer, Nishay Sanan, performed below an objective standard of
reasonableness. At the hearing, Sanan testified that Santos chose to plead guilty after

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No. 08‐1048 Page 3
1 In Spanish, chori can mean knife or small-time crook. HarperCollins Spanish
Unabridged Dictionary 213 (7th ed. 2003).
they discussed the possibility of an entrapment defense several times. Sanan explained
that he concluded that the defense was not tenable after he interviewed Santos 8 to 10
times and read a statement that Santos had written in Spanish for the lawyer. The
English translation of that statement, which the government introduced at the hearing,
runs 25 pages. Santos explains in the statement that he met Moreno through Faustino
Calderon, a friend in Chicago who ran a trucking company. Calderon was a DEA
informant, though he did not make his contacts with Santos at the direction of the
agency, and there is no evidence in the record that attorney Sanan was aware of
Calderon’s connection to the DEA. Santos recounts in his statement that Calderon
called him frequently and left many messages asking for help in finding drivers to
transport drugs across the country. Santos tried to recruit two friends, but they would
not get involved with Calderon unless Santos himself participated, and Santos refused.
That changed, Santos recalls in his statement, after he met Moreno, one of Calderon’s
drivers.
Santos’s statement suggests that Moreno had been sent by Calderon to encourage
Santos to recruit drivers, but instead of finding drivers to transport drugs for Calderon,
Santos teamed up with Moreno to transport drugs for a different source. Santos’s
statement is difficult to understand, but it appears that Santos approached that source,
known as “El Chori,”1 seeking drivers for Calderon, but El Chori suggested instead that
Santos enlist Moreno to transport drugs for El Chori without telling Calderon. El Chori
would not trust Moreno to transport the drugs unless he was accompanied by Santos.
Santos, according to his statement, was reluctant to participate because he was on
probation, so Moreno asked that El Chori send someone else to supervise him. But
El Chori refused to budge, and Santos relented when Moreno promised him a share of
the proceeds and that he would teach him to drive a truck. Moreno made a second trip
for El Chori and, at El Chori’s insistence, Santos rode with Moreno again. When the
time came for a third trip, Santos told El Chori that he did not want to participate
anymore. El Chori agreed at first and offered to accompany Moreno but backed out at
the last minute and insisted that Santos accompany Moreno, as he had done twice
before. Santos told Moreno that he did not want to go, and Moreno told him that was
alright. In the end, though, Santos decided to go by plane and meet Moreno in Chicago,
though he told Moreno not to tell El Chori about the arrangement. This was the trip
that ended in Santos’s arrest.

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Attorney Sanan testified at the hearing that he tried to locate Calderon and
Moreno during the pretrial investigation but without success. Sanan tried to find
Calderon by searching Bureau of Prisons records and looking for his trucking company
but could not find him. Sanan asked the government where Moreno was, but the
government agents said they did not know. Regarding the possibility of an entrapment
defense, Sanan said that he had conveyed to Santos his conclusion that such a defense
could not succeed. As Sanan explained, he believed that Santos could not show
entrapment because, even if Moreno was a government agent, there had been no
significant inducement causing Santos to participate in the drug deal. Sanan was also
concerned that going to trial and putting on an entrapment defense could hurt Santos at
sentencing because he would not get the benefit of an acceptance of responsibility
sentencing discount and that he might be penalized for obstructing justice if he testified
falsely. Sanan testified that, after he explained why making an entrapment defense
would be unwise, Santos decided to plead guilty and seek to cooperate with the
government in an attempt to get a sentence below the 10‐year minimum.
Santos also testified at the evidentiary hearing, but counsel greatly limited the
scope of his testimony. Santos expressed dissatisfaction with one of the lawyers who
represented him before Sanan, but counsel did not ask any questions about Sanan
beyond why Santos hired him and how much Santos paid him. Santos offered no
testimony whatsoever about Sanan’s handling of his case and, therefore, did not
contradict Sanan’s testimony that they had discussed at length a potential entrapment
defense. In addition, Santos offered no testimony at all about his decision to plead
guilty and what motivated that decision.
After the evidentiary hearing, the district court asked Santos to make an offer of
proof concerning the prejudice he allegedly suffered from attorney Sanan’s alleged
shortcomings. Santos explained that he would call at least four witnesses: Calderon,
Moreno, a DEA agent, and the unnamed source who first alerted the DEA to Moreno’s
and Santos’s involvement in drug smuggling. Notably, though, Santos did not say that
he had located Calderon or Moreno or even knew the name of the source. And while
Santos asserted that these witnesses would support his argument that Sanan should
have advised him to go to trial and raise an entrapment defense, he did not identify
their expected testimony except in the most indefinite and vague terms.
The district court denied Santos’s motion, holding that Sanan had not rendered
ineffective assistance. The court assumed that any reasonable defense lawyer would

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have wondered whether Moreno had been acting as a government informant all along.
But, the court continued, given what Santos told Sanan, Sanan correctly concluded that,
even if Moreno was an informant, an entrapment defense was untenable because the
inducement was hardly extraordinary and Santos showed little reluctance to becoming
involved in the drug deal. The court also rejected Santos’s other arguments that Sanan
had been ineffective. After denying Santos’s motion, the district court granted a
certificate of appealability limited to “the claim that the defendant was denied effective
assistance of counsel by his attorneyʹs failure to investigate and present an entrapment
defense.”
On appeal, Santos argues that the district court should have held that his trial
counsel was constitutionally ineffective. When a district court denies a § 2255 motion,
we review fact findings for clear error and we review legal issues de novo. See Suggs v.
United States, 513 F.3d 675, 678 (7th Cir. 2008). To prove ineffective assistance of
counsel, Santos was required to satisfy the familiar two‐pronged test of Strickland v.
Washington, 466 U.S. 668 (1984). That is, he had to show that “counselʹs performance
was deficient” and that “the deficient performance prejudiced the defense.” Id. at 688;
see also Suggs, 513 F.3d at 678. And because he pleaded guilty, Santos could establish
prejudice only by demonstrating that but for counsel’s alleged errors “he would not
have pleaded guilty and would have insisted on going to trial.” Hill, 474 U.S. at 59; see
also Bethel v. United States, 458 F.3d 711, 716‐17 (7th Cir. 2006).
Although Santos’s brief claims that he would not have pleaded guilty absent
attorney Sanan’s alleged errors, there is absolutely no support for this assertion in the
record. As we have held, “a mere allegation by the defendant that he would have
insisted on going to trial is not sufficient to establish prejudice.” Bethel, 458 F.3d at 718.
But Santos’s allegation is not just unsupported, it is also belied by uncontradicted
evidence. Santos has never contradicted his trial counsel’s testimony that they
discussed the entrapment defense at length, that counsel concluded that making the
defense was unwise, and that Santos himself decided to plead guilty and cooperate with
the government in the hopes of getting a lower sentence. Santos only argues generally
that Sanan erred by advising him against raising an entrapment defense. This is wrong:
the court correctly held that an entrapment defense had absolutely no chance of
succeeding. But even if Santos were correct that Sanan erred and an entrapment
defense was even arguable, he would still have the obstacle of showing that had he
been given advice to that effect he would have chosen to go to trial. See United States v.
Cieslowski, 410 F.3d 353, 359 (7th Cir. 2005). Santos has simply never provided any

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support for such a showing; he has never said that knowing what he knows now, he
would have chosen not to plead guilty.
Santos’s failure to focus on the guilty plea is fatal to his claim, but his argument
respecting the possible entrapment defense fails as well. Because Santos’s claim is one
that his lawyer failed to adequately investigate, he had the burden of making a
“‘comprehensive showing as to what the investigation would have produced.’”
Richardson v. United States, 379 F.3d 485, 488 (7th Cir. 2004) (quoting Hardamon v. United
States, 319 F.3d 943, 951 (7th Cir. 2003)). But he did not try to make such a showing. In
his offer of proof to the district court, Santos spoke only in the conditional tense,
explaining what witnesses supposedly “could” explain and what he “believe[d]” their
testimony could establish. Santos did not represent that he had located or interviewed
the four witnesses he intended to call, and indeed, one of them is not even identified by
name in the offer of proof. Santos states repeatedly that more investigation would have
led to the development of an entrapment defense that could have succeeded at trial, but
because he failed to spell out how he intended to prove that contention, this argument
must fail. See Richardson, 379 F.3d at 488 (rejecting failure‐to‐investigate claim where
movant provided no evidence of what further investigation would have revealed);
Hardamon, 319 F.3d at 951 (same).
Santos’s silence on how he could prove an entrapment defense is enough to
doom his claim on its own, but based on the evidence in the record, there is no doubt
that any argument he actually could have made would be doomed as well. This is so
because Santos’s current lawyers misunderstand Santos’s 25‐page narrative. Santos’s
brief asserts that Moreno, a possible government informant, and Calderon, a definite
government informant, pressured Santos to participate in the drug delivery that led to
his arrest. But a close reading of Santos’s statement shows that the three drug‐running
trips that Santos admittedly participated in were done for El Chori without Calderon’s
knowledge. As Santos himself describes the situation in his statement, “Martin
[Moreno] was already working behind Faustino[ Calderon]’s back.” Further‐more,
Moreno was not the one pressuring Santos to participate in the drug smuggling; it was
El Chori who applied the pressure. Moreno twice told Santos that he did not care if
Santos participated, but El Chori insisted. Thus, any inducement came from El Chori, a
man that Santos has never suggested was a government informant. Santos insists that
he was caught up in a scheme of Calderon and Moreno’s devisement, but if anyone was
responsible for the scheme it was El Chori or Santos himself. Moreno met Santos while
looking for drivers to haul Calderon’s drugs, but instead, Santos suggested that Moreno

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haul El Chori’s drugs. Based on Santos’s statement, Moreno was brought into the
scheme by Santos, not the other way around.
Finally, Santos’s entrapment claim is frivolous for yet another reason. To prove
entrapment, a defendant must show both an improper government inducement and a
lack of predisposition to commit the crime. See Mathews v. United States, 485 U.S. 58, 63
(1988); United States v. Bek, 493 F.3d 790, 800 (7th Cir. 2007). Importantly, that
inducement must be “extraordinary.” United States v. Haddad, 462 F.3d 783, 790 (7th Cir.
2006). When a defendant takes a “simple, ordinary opportunity to commit a crime,” he
cannot make an entrapment defense. Id. Thus, even assuming that the scheme was
devised by Calderon and Moreno and both were working for the government, Santos
would not be able to show entrapment because any inducement from those men was
not at all extraordinary. Santos argues that the men badgered and coerced him, calling
several times a day, but persistence alone is not the “extraordinary inducement”
required for a successful entrapment defense. See United States v. Millet, 510 F.3d 668,
676‐77 (7th Cir. 2007). Santos says that he rode along with Moreno the first time
because he wanted to learn to drive a truck, but a promise to teach a defendant to drive
a truck is far from the extraordinary inducement required to show entrapment. Santos
claims that he was reluctant to participate, but he has never argued, let alone testified,
that his reluctance was worn down by anything other than persistence, wanting to
profit from drug sales, and wanting to learn to drive a truck. The district court was,
therefore, correct to conclude that attorney Sanan was not ineffective for failing to
further develop an entrapment defense.
For all these reasons, we AFFIRM the judgment of the district court.

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