Mauricio Ramirez Fernandez v. State of Iowa

IN THE COURT OF APPEALS OF IOWA

No. 17-0132
Filed July 18, 2018

MAURICIO RAMIREZ FERNANDEZ,
Applicant-Appellant,

vs.

STATE OF IOWA,
Respondent-Appellee.
________________________________________________________________

Appeal from the Iowa District Court for Polk County, Michael D. Huppert,

Judge.

Mauricio Ramirez Fernandez appeals the denial of his application for

postconviction relief. REVERSED AND REMANDED.

Angela L. Campbell of Dickey & Campbell Law Firm, PLC, Des Moines, for

appellant.

Thomas J. Miller, Attorney General, and Benjamin M. Parrott, Assistant

Attorney General, for appellee State.

Heard by Vaitheswaran, P.J., and Potterfield and Tabor, JJ.
 2

TABOR, Judge.

Deportation consequences and the duty of criminal defense attorneys again

intersect in this case. Mauricio Ramirez Fernandez1 appeals the denial of

postconviction relief (PCR), contending his attorney was ineffective for failing to

warn him about the immigration and criminal fallout from “turning himself in” to the

Iowa Department of Transportation (DOT) for using a false Social Security number

to register a vehicle. By doing so, Ramirez obtained a conviction for fourth-degree

fraudulent practice. He also faults his attorney for continuing to represent him

while listed as a prosecution witness and for advising him to plead guilty to a crime

of moral turpitude, rendering him ineligible for cancellation of removal proceedings.

Following recent precedent from our supreme court, we conclude no

constitutional right to counsel had attached when attorney Michael Said advised

Ramirez to reveal incriminating facts to the DOT. But we do find Said operated

under an actual conflict of interest in continuing to represent Ramirez throughout

the criminal case while listed as a State’s witness and not informing Ramirez of

this fact. We further find Said breached a duty in failing to adequately inform

Ramirez of the immigration consequences of his plea and Ramirez demonstrated

prejudice by rationally insisting he would have stood trial if he knew the reduced

charge carried the same prospect for removal as conviction on the original offense.

We reverse his conviction and remand for Ramirez to proceed with non-conflicted,

competent counsel.

1
Throughout the record, the applicant-appellant is identified by the surname Ramirez, so
we will do the same in this opinion.
 3

Because we resolve the appeal on the conflict-of-interest and failure-to-

advise issues, we need not address Ramirez’s two remaining claims: (1) that

counsel was ineffective for not moving to suppress privileged information and

(2) that the district court abused its discretion in sustaining an objection to

questions concerning Said’s pattern of failing to properly advise clients of known

immigration consequences of their criminal convictions.

I. Facts and Prior Proceedings

Ramirez is a Mexican citizen, who has been living in the United States since

1996. He and his wife, also a Mexican national, have two children, one of whom

is an American citizen. In 2011, Ramirez was arrested while at work without proof

of authorization to be in the United States. Immigration authorities began removal

proceedings against Ramirez, and he retained attorney Said to represent him in

his immigration case. Said filed an application for cancellation of removal for

Ramirez.2

In the course of his representation in the immigration case, Said advised

Ramirez to get a driver’s license. Ramirez confided in Said that he had used a

false Social Security number to register a car. On July 20, 2011, Said sent an

email to a DOT investigator with whom he had previous dealings, saying,

I have another client who used a false SS# to register his car
and House trailer. He now has a bona fide SS# and wants to get his
DL and register his car and Trailer with the correct number. I am
seeing you tomorrow and could bring him in.

2
Immigrants in removal proceedings may obtain a cancellation of removal, if eligible. See
8 U.S.C. § 1229b(b)(1) (2011). Immigrants are ineligible if they have been convicted of
an aggravated misdemeanor (8 U.S.C. § 1227(a)(2)(A)(iii)) or any crime considered to be
a “crime of moral turpitude.” 8 U.S.C. § 1229b(b)(1)(C), 1182(a)(2). While an application
for cancellation of removal is pending, the applicant can obtain work authorization and a
Social Security number.
 4

False SS# is [###-##-####].
Let me know what you want to do.

According to his report narrative, the investigator searched DOT databases and

discovered an application for vehicle registration dated October 27, 2008, under

the false Social Security number Said provided. On the following day, July 21,

Said and Ramirez met with the investigator. At the meeting, Ramirez provided a

written statement labeled, “VOLUNTARY STATEMENT (NOT UNDER ARREST)”:

“I used a made up Social Security number to register a car in Polk County, Iowa

on 10/27/08.” The investigator issued Ramirez a “citation and complaint” charging

him with fraudulent practice in the third degree, in violation of Iowa Code

section 714.11(3) (2008). This is an aggravated misdemeanor under Iowa law.3

Iowa Code § 714.11(3).

At the PCR trial, Ramirez testified he did not know Said had informed the

DOT of his false Social Security number and falsely registered car until after he

had been charged. He also testified Said never told him he would be charged with

a crime if he went to the DOT. He further testified he was never told the offense

would make him ineligible for cancellation of removal. He insisted if he had known,

he would not have gone to the DOT. Ramirez recalled Said telling him if he agreed

to everything he would be “alright.” Ramirez had limited English-language skills,

and Said had limited Spanish-language proficiency. No interpreter was present

during the DOT meeting. Afterward, Said brought Ramirez to his law office and

3
But under federal law, it is considered an aggravated felony; the immigration
consequence would have included ineligibility for cancellation of removal. See U. of Iowa
C. of L., Advanced Immigration Law & Policy Project, Immigration Consequences for Iowa
Criminal Statutes 213-14 (2015), hereinafter Immigration Consequences.
 5

asked his Spanish-speaking secretary to translate what had happened. Ramirez

testified he did not understand he had been charged with a crime until the meeting

in Said’s office. At that point, Said took a $2500 retainer to represent Ramirez in

the criminal proceedings.

Said testified Ramirez was aware Said was going to disclose the

incriminating information to the DOT before the attorney did so, even though it was

protected by attorney-client privilege. Said recalled telling Ramirez he would face

a criminal charge. Said also explained he thought Ramirez should get a driver’s

license because the attorney did not anticipate Ramirez would refrain from driving,

and eventually Ramirez might incur a more serious conviction that would severely

impact his immigration status. The benefit of going to the DOT, according to Said,

was Ramirez could obtain a driver’s license and be charged with an aggravated

misdemeanor only. Said noted other noncitizens in similar circumstances had

been charged with the felonies of forgery and identity theft. Said did not advise

Ramirez not to drive or suggest that was an option.

When the State filed the trial information charging Ramirez with fraudulent

practice, it listed two witnesses: the DOT investigator and Said. Neither Said nor

the State brought this potential conflict to the district court’s attention; the court did

not mention the witness list or inquire further. At the PCR trial, Ramirez testified

he was not aware, and Said never told him, Said was listed as a witness.

According to Ramirez, Said did not inform him that if he went to trial Said could be

called to testify against him. Said never obtained a waiver of conflict from Ramirez.

Said continued to represent Ramirez in both his immigration and criminal cases;

Ramirez continued to pay Said for his representation.
 6

On Said’s advice, Ramirez pleaded guilty to a reduced charge of fraudulent

practice in the fourth degree, in violation of Iowa Code section 714.12, classified

as a serious misdemeanor.4 The United States government then filed a motion to

pretermit Ramirez’s application for cancellation of removal, arguing the conviction

was for a crime of moral turpitude, rendering Ramirez ineligible. The federal

immigration court agreed with the government that the conviction was a crime of

moral turpitude and granted the motion, subjecting Ramirez to removal

proceedings.

When asked at the PCR trial whether he advised Ramirez about the

immigration consequences of the plea, Said responded it was a standard

procedure of his office to “explain that any criminal matter has an immigration

consequence,” including possible removal. He did not know whether he or another

attorney in his office had explained the matter to Ramirez. He testified he

4
No evidence in the record supports the element of fraudulent practice in the fourth degree
that services involved “exceed[] two hundred dollars but do[] not exceed five hundred
dollars.” Iowa Code § 714.12. Fraudulent practice in the third degree applies where “it is
not possible to determine an amount of money or value of property and services involved.”
Iowa Code § 714.11(1)(c). The DOT investigative report concluded charging third-degree
fraudulent practice was appropriate “since a dollar amount is not determinable by the use
Mr. Ramirez had with the car.” The investigator also discovered Ramirez used the Social
Security number for wages but gave only a verbal warning for that act. The trial
information (and subsequent amendment) do not show the amount involved. The plea
agreement states the defendant was pleading to “Fraudulent practices 4th in violation of Iowa Code Section(s) 714.12.” Ramirez provided the following
factual basis: “I went and registered a car using a SS to which was not mine.” Nothing in
the plea record identified the dollar amount involved. Our supreme court has rejected the
notion that counsel may have strategic reasons for permitting a client to plead guilty
notwithstanding the lack of a factual basis. State v. Hack, 545 N.W.2d 262, 263 (Iowa
1996) (“Endorsing such strategies . . . would erode the integrity of all pleas and the public’s
confidence in our criminal justice system.”). But because Ramirez has not challenged his
counsel’s performance related to the factual basis, we do not address that issue.
 7

subjectively believed fraudulent practice was not a crime of moral turpitude. But

on cross-examination, he stated he told Ramirez “some people” consider

fraudulent practice a crime of moral turpitude. And in depositions, he admitted

knowledge of two cases from the United States Court of Appeals for the Eighth

Circuit concluding it is a crime of moral turpitude. Said was asked, “[A]t the time

[Ramirez] took the plea, it was a settled matter for at least the 8th Circuit that it

was a [crime of] moral turpitude; is that correct?” Said answered, “Yeah.” When

asked, “Did you advise—specifically advise [Ramirez] that he was pleading to a

crime of moral turpitude?” Said answered, “No, I don’t remember if I did specifically

tell him that.”

Although the district court found Said’s performance was deficient in not

sufficiently advising Ramirez on the immigration consequences of the plea, it found

no prejudice because Ramirez had not shown he would have insisted on going to

trial for the greater offense. Thus, the district court denied Ramirez’s application

for PCR. Ramirez appeals.

II. Analysis of Sixth Amendment Claims

We review PCR proceedings for correction of legal error unless they raise

constitutional issues, in which case our review is de novo. Perez v. State, 816

N.W.2d 354, 356 (Iowa 2012). Here, Ramirez’s claims of ineffective assistance of

counsel call for de novo review. Diaz v. State, 896 N.W.2d 723, 727 (Iowa 2017).

Even under de novo review, we accord weight to the district court’s credibility

findings. Ledezma v. State, 626 N.W.2d 134, 141 (Iowa 2001).

To succeed, Ramirez must establish both: (1) counsel failed to perform an

essential duty, and (2) that failure resulted in prejudice. See Strickland v.
 8

Washington, 466 U.S. 668, 687 (1984). To establish prejudice, he must show a

reasonable probability exists that, but for counsel’s errors, the result of the

proceeding would have been different. State v. Carroll, 767 N.W.2d 638, 641 (Iowa

2009). In a guilty-plea case, the prejudice element “focuses on whether counsel’s

constitutionally ineffective performance affected the outcome of the plea process.”

Hill v. Lockhart, 474 U.S. 52, 59 (1985). To satisfy the prejudice requirement under

Hill, Ramirez must show a reasonable probability exists that, but for counsel’s

faulty advice, he would not have pleaded guilty and would have insisted on going

to trial. See id.; see also State v. Straw, 709 N.W.2d 128, 138 (Iowa 2006). In an

immigration-consequences case, an applicant “must convince the court that a

decision to reject the plea bargain would have been rational under the

circumstances.” Padilla v. Kentucky, 559 U.S. 356, 372 (2010).

Whether defense counsel had an actual conflict of interest is a mixed

question of law and fact. State v. Mulatillo, 907 N.W.2d 511, 517 (Iowa 2018)

(applying de novo review to underlying question whether constitutional right to

counsel was violated). Ramirez argues his case under both the Sixth Amendment

to the U.S. Constitution5 and Article I, Section 10 of the Iowa Constitution.6

5
“In all criminal prosecutions, the accused shall enjoy the right . . . to have the Assistance
of Counsel for [their] defence.” U.S. Const. Amend. VI.
6
“In all criminal prosecutions, and in cases involving the life, or liberty of an individual the
accused shall have a right to . . . have the assistance of counsel.”
 9

1. Attachment of Right to Counsel

Ramirez first contends Said provided ineffective assistance of counsel

when he failed to advise Ramirez of the consequences of “turning himself in” at

the DOT. Because Said offered the alleged bad advice before a criminal

investigation started, the State contends Ramirez did not yet enjoy the

constitutional right to assistance of counsel.

Both the Sixth Amendment and Article I, Section 10 provide an “accused”

with the right to “the assistance of counsel.” The “right to counsel is the right to the

effective assistance of counsel.” See Strickland, 466 U.S. at 686 (emphasis

added) (quoting McMann v. Richardson, 397 U.S. 759, 771 n.14 (1970)); State v.

Schlitter, 881 N.W.2d 380, 388 (Iowa 2016). Conversely, “[w]ithout a right to

counsel, a defendant also has no commensurate right to effective assistance from

that counsel.” State v. Dudley, 766 N.W.2d 606, 617 (Iowa 2009) (citation omitted).

The district court ruled Ramirez was not entitled to counsel when going to

the DOT. The court cited State v. Senn, for the proposition that the right to counsel

“under both the State and Federal Constitutions ‘attaches at or after the initiation

of adversary proceedings against the defendant, whether by way of formal charge,

preliminary hearing, indictment, information, or arraignment.’” 882 N.W.2d 1, 8

(Iowa 2016) (quoting State v. Hensley, 534 N.W.2d 379, 382 (Iowa 1995)). The

court rejected Senn’s claim he had a right to counsel before taking a breath test

when a police officer stopped his car under suspicion of driving while intoxicated.

Id. at 6. The three-member plurality opinion concluded the right to counsel under

the Iowa Constitution does not attach until formal charges have been filed. Id. at
 10

31.7 Ramirez contends because Senn was a plurality opinion, the question of

when the right to counsel attaches was left open.8

After the parties filed their briefs in the instant case, the Iowa Supreme Court

decided Ruiz v. State, 912 N.W.2d 435 (Iowa 2018), which addressed the

attachment of the right to counsel in nearly identical circumstances. The same

attorney, Michael Said, advised his immigration client, who had a pending

application for cancellation of removal, to obtain a driver’s license.9 Ruiz, 912

N.W.2d at 437-38. Without asking about any past conduct, Said arranged for Ruiz

to apply for a driver’s license. Id. In doing so, the DOT discovered Ruiz had

previously registered vehicles under a false Social Security number. Id. The same

DOT investigator involved in Ramirez’s case asked Ruiz to fill out a voluntary

statement and charged him with the same offense as Ramirez, fraudulent practice

in the third degree. See id. Ruiz also ultimately pleaded guilty to fraudulent

practice in the fourth degree. Id. at 438. As a result, Ruiz’s application for

cancellation was denied, and he was subjected to removal proceedings. Id. Ruiz

filed for PCR, asserting Said had breached an essential duty by advising him to

obtain a driver’s license. Id.

7
Chief Justice Cady filed a separate opinion concurring in the result only.
8
Justices Wiggins, Hecht, and Appel dissented. Justice Wiggins wrote to criticize the
plurality for disregarding the applicability of the right to counsel under the Iowa Constitution
“in cases involving the life, or liberty or an individual.” Senn, 882 N.W.2d at 32-33
(Wiggins, J., dissenting) (quoting Art. I, sect. 10). Justice Appel wrote to conclude the
right to counsel under the Iowa Constitution attached at the “critical stage of the
prosecution” when Senn was confronted with an implied-consent request. Id. at 68 (Appel,
J., dissenting) (citing United States ex rel. Hall v. Lane, 804 F.2d 79, 81 (7th Cir. 1986)
(“The Sixth Amendment, . . . guarantees the right to counsel during all critical stages of
prosecution.” (citations omitted)).
9
Said has been disciplined for ethical violations in his representation of clients, particularly
in his immigration practice. See, e.g., Iowa Supreme Ct Attorney Disciplinary Bd. v. Said,
869 N.W.2d 185 (Iowa 2015).
 11

Our supreme court, ruling under both the federal and state constitutions,

found, “[T]he right [to counsel] ‘does not attach until a prosecution is commenced.’”

Id. at 439 (quoting Rothgery v. Gillespie Cty, 554 U.S. 191, 198 (2008)). “A

prosecution commences at ‘the initiation of adversary judicial criminal

proceedings.’” Id. (quoting Rothgery, 554 U.S. at 198).10 The court noted at the

time of the alleged breach, Ruiz had not been arraigned or even charged; in fact,

“no criminal investigation had even begun.” Id. Because the right to counsel had

not attached, Ruiz could not show a denial of effective assistance of counsel. Id.11

Ramirez seeks to distinguish his case from Senn and Ruiz by arguing a

criminal investigation commenced when Said informed the investigator of

Ramirez’s situation by email the day before their meeting. He contends the right

to counsel attached because he was “accused” by virtue of a criminal investigation

before any prosecutorial involvement. Here, the DOT investigator used the false

Social Security number disclosed by Said to track down Ramirez’s fraudulent

registration, secured a signed admission from Ramirez, and issued a citation at

the in-person meeting. Ramirez asserts the DOT investigator would not have

connected him with any unlawful conduct without Said’s tip-off. Said

acknowledged knowing that disclosure would result in criminal charges, but he

revealed the otherwise privileged information anyway.

10
Neither article I, section 10 nor the Sixth Amendment apply in immigration cases. Ruiz,
912 N.W.2d at 441.
11
Justice Appel, joined by Justices Wiggins and Hecht, specially concurred, agreeing the
right to counsel under either the federal or state constitution did not attach when Ruiz’s
lawyer “gave him poor advice in his office. At that point, the adversarial power of the
government had not focused on him at all. Indeed no investigation of any kind was
underway.” Id. at 444 (Appel, J., specially concurring). But the special concurrence did
not agree with “the bright-line rule that invariably requires that the state file a piece of
paper in a court in order for the right to counsel to attach.” Id. at 444.
 12

Ramirez’s case bears a factual difference from Ruiz. Here, Said emailed

the DOT investigator a day in advance, enabling the investigator to verify the

incriminating information and obtain a “voluntary statement” from Ramirez during

the meeting. But we cannot find this slight departure justifies finding the right to

counsel attached before the alleged breach of duty.

In another recent right-to-counsel case, State v. Green, the supreme court

reiterated the principle that “the criminal prosecution required by [the Sixth

Amendment] exists once a complaint has been filed and an arrest warrant has

been issued.” 896 N.W.2d 770, 777 (Iowa 2017). But, “once a complaint has been

filed and an arrest has occurred, a police interview is no longer a criminal

investigation. Instead, it takes the shape of an accusation.” Id. In Green, the

defendant willingly participated in a police interview without being Mirandized.12

He was later charged with murder. The court found

Green was not formally or informally an “accused,” and the interview
was not a “criminal prosecution” . . . . Green appeared voluntarily . .
. . He could have left . . . or stopped the interview at any time. There
was no warrant for his arrest, and there were no charges filed against
him.

Id. at 778.

When Ramirez attended the DOT meeting, some investigation had taken

place; the investigator interviewed Ramirez and obtained a “voluntary statement”

admitting he “made up a Social Security number to register a car.” The investigator

did not issue the citation until the end of the meeting. The investigator noted he

was not arresting Ramirez. Even if Said’s email disclosure “tipped off” the

12
Miranda v. Arizona, 384 U.S. 436, 498 (1966).
 13

investigator, we cannot say from the existing precedents or the circumstances of

Ramirez’s case that either an investigation or a prosecution were underway at the

time of the alleged breach. See Ruiz, 912 N.W.2d at 443 (“Bad legal advice can

lead to a criminal investigation in a variety of contexts. . . . Still, it isn’t ineffective

assistance unless the bad advice occurs in a criminal case or an Iowa case

‘involving the life, or liberty of an individual.’”). Accordingly, the right to effective

counsel had not yet attached.13

2. Representation While Conflicted

Ramirez next contends Said provided ineffective assistance of counsel in

continuing to represent him while being listed as a witness for the State.14 When

asked at the PCR hearing whether he reviewed the trial information with Ramirez

or informed Ramirez he was listed as a witness, Said testified, “More than likely

we would have told him, yeah.” But in depositions, Said testified he never

discussed the possibility he could testify with Ramirez because the case never

went to trial. Said further testified if the case had gone to trial, he would have

withdrawn. Ramirez characterizes Said’s representation before and during the

plea proceedings as a “glaring conflict of interest.”

13
In reply briefing, Ramirez raises Said’s alleged violations of the Iowa Rules of
Professional Conduct as proof he breached a duty and argues it is good public policy for
the right to counsel to attach earlier in this case. Ramirez complains, “It would be
fundamentally unfair to enable an attorney to continue this business model of retaining
clients, gaining confidential information, disclosing that confidential information to law
enforcement to initiate criminal charges, and then demand another retainer to represent
them” in the criminal case. First, we generally do not address issues first raised in a reply
brief. Villa Magana v. State, 908 N.W.2d 255, 260 (Iowa 2018). Second, the principles
outlined above still govern: whatever duties Said may have breached—those of
professional competence or lawyerly ethics—the constitutional right to effective
assistance had not yet attached at the time of the conduct alleged here.
14
The State does not dispute the right to counsel had attached at this point.
 14

The State points out that in the conflict-of-interest context, appellate courts

do not require a showing of Strickland-type prejudice—only the existence of an

“actual” conflict of interest, which is a conflict that “adversely affects counsel’s

performance.” See Mickens v. Taylor, 535 U.S. 162, 174 (2002); State v.

Vaughan, 859 N.W.2d 492, 500 (Iowa 2015). The State contends no evidence

proves any aspect of Said’s performance was motivated by his appearance on the

State’s witness list. The State also asserts Ramirez waived any potential conflict

of interest by pleading guilty because the claimed conflict was not intrinsic to the

guilty plea.15

a. Objection Intrinsic to Guilty Plea

Generally, when criminal defendants plead guilty, they waive all objections

and defenses, including claims concerning the performance of counsel. Castro v.

State, 795 N.W.2d 789, 792 (Iowa 2011). But our supreme court has recognized

an exception to this rule for irregularities that are intrinsic or, in other words, bear

on the knowing and voluntary nature of the plea. Id. A claim raised by a

postconviction-relief applicant may survive a guilty plea if counsel’s pre-plea

performance rendered the plea involuntary or unintelligent. See id. at 793

(discussing ineffective-assistance claim).

Before accepting a guilty plea, the district court must decide if it is being

entered voluntarily and intelligently and has a factual basis. Iowa R. Crim.

P. 2.8(2)(b). The court must address defendants personally and determine they

15
The State complains Ramirez is presenting a different issue on appeal than he did in
the PCR proceedings. Because we read his amended PCR application as encompassing
this issue, we find error was preserved.
 15

understand, among other things, that they have “the right to assistance of counsel,

the right to confront and cross-examine witnesses against the defendant . . . [and]

the right to present witnesses in [their] own behalf.” Id. at 2.8(2)(b)(4).

Although the court engaged in a short colloquy with Ramirez facilitated by

an interpreter, and these rights were reiterated in the written plea, we are not

convinced Ramirez could understand the import of the trial rights he was giving up

without knowing the State planned to call his own attorney as a witness against

him. Because the record does not show Ramirez realized his attorney—retained

to represent him on both immigration and criminal matters—was listed as one of

two witnesses for the prosecution, we cannot be satisfied Ramirez fully

appreciated the ramifications of pleading guilty. Said’s pre-plea advice was tainted

by the fact he tipped off authorities to Ramirez’s crime and would be summoned

to testify about his client’s wrongdoing if the plea negotiations failed.16 Ramirez’s

unawareness of his attorney’s potential conflict of interest impacted the knowing

and voluntary nature of the plea. See Castro, 795 N.W.2d at 792. Ramirez could

not accurately assess the wisdom of accepting the plea offer, as recommended by

his attorney, while in the dark about the State’s intention to extract incriminating

information from his attorney should the case proceed to trial. Because his conflict

claim was intrinsic to the plea, Ramirez did not waive this issue by pleading guilty.

16
We find it significant that Said believed being listed as a prosecution witness would have
presented an actual conflict of interest had the case proceeded to trial. His belief
undermines the State’s argument on appeal that Said was not an essential witness and
the prosecution could have proved its case by calling only the DOT investigator.
 16

b. Adverse Effect of Conflict on Counsel’s Performance

“A lawyer shall not act as advocate at a trial in which the lawyer is likely to

be a necessary witness . . . .” Iowa R. Prof. Conduct 32:3.7.17 Ramirez points to

this rule in asserting Said’s conflict of interest. While the rules of professional

conduct provide guidance on the conflict question, they are not alone dispositive.

See State v. McKinley, 860 N.W.2d 874, 881 (Iowa 2015).

The parties debate the relevance of the rule, given the fact Ramirez entered

a guilty plea. The State insists any potential conflict never materialized into an

actual conflict because the case never proceeded to trial and it was unlikely Said

would have been called to testify if it had. But Ramirez cites State v. Vanover,

where the district court removed an attorney who was listed as a witness for the

State over the defendant’s objections before the case went to trial. 559 N.W.2d

618, 625 (Iowa 1997). The supreme court held, “A trial court may . . . disqualify

counsel if necessary to preserve the integrity, fairness, and professionalism of trial

court proceedings.” Id. at 626.

Where the district court does not inquire into a potential conflict before trial,

reversal is not automatic. “[T]he defendant still has to establish that the alleged

conflict materialized into an actual conflict.” Vaughan, 859 N.W.2d at 500 (citing

Mickens, 535 U.S. at 172–74).18 To demonstrate an actual conflict, Ramirez must

show being listed as a State’s witness adversely affected Said’s performance. See

17
The rule lists three exceptions: (1) the lawyer’s testimony relates to an uncontested
issue, (2) the testimony relates to nature and value of legal services rendered in the case,
or (3) disqualification of the lawyer would work a substantial hardship on the client. Iowa
R. Prof. Conduct 32:3.7(a)(1)–(3).
18
The Sixth Amendment requires automatic reversal “only when the trial court refuses to
inquire into a conflict of interest over defendant’s or counsel’s objection.” Vaughan, 859
N.W.2d at 500.
 17

id. “[A]n adverse effect occurs when counsel fails to pursue a plausible strategy

or tactic due to the existence of a conflict of interest.” Id. at 501 (citing Noe v.

United States, 601 F.3d 784, 790 (8th Cir. 2010)).

It is hard to glean Said’s exact motivation for continuing to represent

Ramirez without informing him of the potential conflict. But the record reveals gaps

in the efforts exerted by Said (perhaps cognizant of his multiple prior disciplinary

actions) on Ramirez’s behalf, suggesting plausible defense strategies were not

explored. Said’s conduct during plea negotiations suggests a “serious potential

that [Said’s] loyalties would . . . be divided” between Ramirez and himself. See

Vanover, 559 N.W.2d at 631.

Significantly, Said did not ask the State to remove him as a witness or raise

the conflict for the court to address. And he did not secure a waiver of the potential

conflict from Ramirez, or even recall informing his client of the potential he would

testify for the State should the matter proceed to trial. It is the rare case where the

State lists defense counsel as one of the key fact witnesses against the client.

See, e.g., id. at 625 (recognizing defense attorney listed as prosecution witness

because he obtained statements from co-defendants had a “serious potential

conflict of interest”). A more common scenario is the danger of divided loyalties

based on the representation of potential witnesses against the client. See, e.g.,

McKinley, 860 N.W.2d at 877 (public defenders in the same office represented the

defendant and witnesses against him); Vaughan, 859 N.W.2d at 498–99 (counsel

represented both the defendant and a potential witness against defendant); Ibarra

v. State, No. 14-2007, 2015 WL 6508952, at *2 (Iowa Ct. App. Oct. 28, 2015)

(public defenders in the same office had represented decedent and several
 18

witnesses against the defendant in a murder trial). Given Said’s belief he would

have been required to withdraw if the case proceeded to trial, we find his

performance in negotiating a favorable plea and advising his client about the

wisdom of accepting the plea offer was adversely affected.

In addition, Said’s own conduct could have been the subject of pretrial

defense motions. As Ramirez suggests on appeal, a plausible tactic would have

been seeking to suppress the original email from Said to the DOT investigator

based on a breach of attorney-client privilege. Because of his conflict, Said was

unlikely to file such a motion as it could expose him to potential attorney discipline.

Said’s decision to share incriminating facts about his client and his resulting

position as a State’s witness, left counsel unable to see or pursue the full range of

options available in Ramirez’s defense and, thus, adversely affected his

representation. See Vaughan, 859 N.W.2d at 501 (explaining “an adverse effect

occurs when counsel fails to pursue a plausible strategy or tactic due to the

existence of a conflict of interest” (citation omitted)). A non-conflicted attorney

would have had the freedom to follow a strategy to suppress the email and the

resulting tip-off to law enforcement.19

19
We look to Justice Appel’s special concurrence in Vaughan where the attorney helped
a witness approach the State with evidence against his own client:
To me, it is astonishing that a lawyer representing an accused in a
criminal matter would facilitate the discovery of evidence by the prosecution
adverse to his or her client. Yet, this is precisely what occurred here. When
Vaughan’s attorney learned from Cline [whom the attorney also
represented] that Cline wanted to speak to the prosecutor about Vaughan,
it was obvious Cline did not intend to assist in Vaughan’s defense. At that
point, Vaughan’s attorney should have refused to contact the prosecutor
on behalf of Cline. Instead, he facilitated the prosecution’s receipt of
evidence adverse to his client. When he did so, he was not acting zealously
on behalf of Vaughan. It was a disloyal act.
Vaughan, 859 N.W.2d at 503.
 19

Further, Said did not depose the State’s listed witnesses to test the strength

of the prosecution’s case, explain to Ramirez what the witnesses would say, or

determine the viability of filing various pretrial motions. A non-conflicted attorney

could have done so without the absurdity of having to question himself.

The State emphasizes “there was no trial in this case, and trial was never

likely.” But a trial was not essential to showing Said’s representation through the

plea proceedings was adversely affected by the conflict. The State insists

Ramirez’s singular strategy was to avoid trial and plead guilty. That is true only to

the extent Ramirez wished to remain eligible for cancellation of removal by

accepting the plea offer—his entire representation by Said, an immigration

attorney, was motivated by a desire to avoid removal proceedings. By pleading

guilty as he did here, Ramirez did not escape that consequence. The pull between

Said’s obligation to testify if called by the State at trial and his duty to vigorously

represent Ramirez at the plea stage materialized into an actual conflict of interest

adversely affecting his representation of Ramirez. His counsel’s actual conflict of

interest rendered Ramirez’s plea unknowing and involuntary. We reverse the

conviction and sentence and remand for further proceedings consistent with this

opinion.

Having concluded reversal of Ramirez’s conviction is warranted on the

conflict-of-interest ground, we could stop here. But because we find an alternative

ground for reversal based on attorney Said’s failure to adequately advise Ramirez

of the immigration consequences of his guilty plea, we choose to address that

issue as well.
 20

3. Guilty Plea to a Crime of Moral Turpitude

Ramirez contends Said was remiss in recommending he plead guilty to

fourth-degree fraudulent practice without adequately advising him of the

immigration consequences—specifically that it was a crime of moral turpitude that

would result in Ramirez losing eligibility for cancellation of removal. The State

argues Said met his duty by generally advising Ramirez the plea could have

adverse immigration consequences because characterization of the crime as one

of moral turpitude was an unsettled question of federal immigration law. The State

further contends Ramirez is unable to show prejudice because he had no plausible

chance of acquittal and would not have reasonably rejected the plea offer to a

lesser offense.20

An attorney’s performance is constitutionally deficient when the attorney

fails to advise the defendant on the immigration consequences of pleading guilty.

Padilla, 559 U.S. at 368; Diaz, 896 N.W.2d at 729. The applicant must show

counsel’s performance “fell below an objective standard of reasonableness.” Diaz,

896 N.W.2d at 728 (citation omitted). In defining this standard, “We look to the

practice and expectations of the legal community.” Id. (citation omitted). If an

applicant satisfies the first prong, the next step is proving prejudice. In this context,

20
Ramirez also suggests, as he did at the PCR trial, that Said should have done more to
negotiate a guilty plea to a misdemeanor arguably outside the class of offenses
considered “crimes of moral turpitude” and therefore avoid ineligibility for cancellation of
removal. He mentions this claim in passing, but it is not fully briefed for our review.
Ramirez does not specify what statutory provision would have made for a more desirable
plea offer. We will not consider this undeveloped argument beyond noting, again, the
record reveals no factual basis for the plea to fourth-degree fraudulent practice. The
record does show a factual basis for third-degree fraudulent practice, which is an
aggravated misdemeanor and would have rendered Ramirez ineligible for cancellation of
removal. See Immigration Consequences, supra 213–14.
 21

an applicant proves prejudice by showing he or she would not have pleaded guilty

and instead would have insisted on going to trial. Id. “This does not mean the

defendant must show he or she would have prevailed at trial.” Id. at 729. Only

that “the ‘decision to reject the plea bargain would have been rational under the

circumstances.’” Id. (quoting Padilla, 559 U.S. at 372).

The district court found Said failed in an essential duty—Said knew the

Eighth Circuit considered fraudulent practice to be a crime of moral turpitude and

still did not specifically recall advising Ramirez of that fact. The court found Said

“was personally aware that fraudulent practice in the fourth degree would be

considered a crime of moral turpitude and result in the denial of [Ramirez’s]

cancellation of removal.” On appeal, the State suggests the immigration

consequences of the plea were debatable.21 But the court found, “The deportation

consequences of the particular plea were not unclear or uncertain to Said—he was

fully aware of the consequences his client would face.” The court concluded

because a “reasonably competent” attorney would have advised a client of these

consequences, Said failed in an essential duty. Upon our review of the record and

giving appropriate weight to the district court’s credibility assessments, we agree

Said’s performance fell below an objective standard of reasonableness.

21
In support of this position, the State provides additional authority. See Martinez v.
Sessions, 892 F.3d 655 (4th Cir. 2018); Lozano-Arredondo v. Sessions, 866 F.3d 1082
(9th Cir. 2017);. But it is difficult to see how these more recent cases from other circuits
would excuse Said’s deficient performance. The Eighth Circuit has concluded crimes
involving fraudulent use of a Social Security number are crimes of moral turpitude. See
Guardado-Garcia v. Holder, 615 F.3d 900, 902 (8th Cir. 2010) (conviction for fraudulent
use of Social Security number under the Social Security Act constituted a crime of moral
turpitude as involving an intent to deceive); Lateef v. Dept of Homeland Security, 592 F.3d
926, 929 (8th Cir. 2010) (the Board of Immigration Appeals correctly concluded that the
crime of using an unlawfully obtained Social Security number is a crime of moral turpitude,
as it involves an intent to deceive).
 22

But, the district court went on to find Ramirez had not shown prejudice. The

court saw no reasonable probability Ramirez would not have pleaded guilty and

insisted on going to trial given the fact he admitted his actions to the DOT. The

court concluded forgoing a plea to a lesser offense would not have been rational

and negotiating a plea to a different subsection—not considered a crime of moral

turpitude—would have been unlikely.

We disagree with the district court on the prejudice prong. Ramirez testified

if he had been told pleading guilty would have resulted in his removal from the

country, he would have gambled on a trial. By going to trial, Ramirez would have

faced conviction for third-degree fraudulent practices, categorically a crime that

would make him ineligible for cancellation of removal, as an aggravated

misdemeanor.22 But pleading guilty to fourth-degree fraudulent practice—

considered to be a crime of moral turpitude—posed the same risk of removal.

If Ramirez had been correctly advised of the immigration consequences, he

could have “rationally decided to hold the State to its burden of proof” since he had

nothing to lose by doing so. Diaz, 896 N.W.2d at 734; see State v. Ali, No. 16-

0378, 2017 WL 936112, at *4 (Iowa Ct. App. Mar. 8, 2017) (recognizing “different

calculus” confronting non-U.S. citizen in evaluating plea offer and vacating guilty

plea where immigrant defendant established he would not have pleaded guilty had

he known deportation consequences of conviction); see also People v. Morones-

Quinonez, 363 P.3d 807, 811 (Colo. App. 2015) (explaining “strength of the

22
An aggravated misdemeanor carries other immigration consequences including
mandatory detention and a permanent reentry bar. See Univ. of Iowa Coll. of Law
Advanced Immigration Law & Policy, Immigration Consequences for Iowa Criminal
Statutes (2015) 213.
 23

evidence against the defendant may not be as probative of rationality as it would

be in a nonimmigration case” (citation omitted)); Sial v. State, 862 N.E.2d 702, 706

(Ind. Ct. App. 2007) (reversing denial of postconviction relief—where applicant had

been living in United States for twenty years and had a wife and American-citizen

daughter—to find he would have forgone plea and proceeded to trial). Ramirez

had been in the United States for fifteen years. He was married and the younger

of his two children was born in the United States. He testified he wanted to stay in

the United States and would not have pleaded guilty if he had known it would result

in his removal. Ramirez established it would have been rational to reject the plea

agreement and that he received ineffective assistance.

With a non-conflicted attorney who competently advised him about the

immigration consequences, Ramirez might have also pursued pretrial evidentiary

claims or insisted on negotiating a more favorable plea. Based on this ineffective

assistance claim, as well as the conflict-of-interest ground, we reverse Ramirez’s

conviction and remand for further proceedings.

REVERSED AND REMANDED.