Court of Appeals of Indiana | Opinion 18A-CT-514 | September 25, 2018 Page 1 of 15

ATTORNEY FOR APPELLANT

Carrie Castro

Law Office of Carrie Castro

Merrillville, Indiana

ATTORNEYS FOR APPELLEE

David C. Jensen

Robert J. Feldt

Eichhorn & Eichhorn, LLP

Hammond, Indiana

I N T H E

COURT OF APPEALS OF INDIANA

Michael D. Goodwin,

Appellant-Plaintiff,

v.

David L. DeBoer,

Appellee-Defendant.

September 25, 2018

Court of Appeals Case No.

18A-CT-514

Appeal from the Lake Superior 

Court

The Honorable Calvin D. 

Hawkins, Judge

Trial Court Cause No.

45D02-1709-CT-88

Najam, Judge.

Statement of the Case

[1] Michael D. Goodwin sued his former attorney David L. DeBoer for legal 

malpractice, breach of fiduciary duty, and fraudulent concealment after 

Goodwin pleaded guilty in a federal criminal cause of action in which DeBoer, 

along with two other attorneys, had represented Goodwin. The essence of 
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Goodwin’s civil claims against DeBoer are that, had DeBoer rendered 

competent representation to Goodwin in the federal action, Goodwin would 

not have pleaded guilty. But, after an evidentiary hearing before the federal

district court in a post-conviction proceeding, the court rejected the factual and 

legal issues that Goodwin now relies on to support his theory that he would not 

have pleaded guilty had DeBoer acted differently. Accordingly, as a matter of 

law Goodwin is precluded from now arguing that DeBoer’s alleged malpractice 

proximately caused Goodwin to plead guilty. As such, we affirm the trial 

court’s entry of summary judgment for DeBoer.

Facts and Procedural History

[2] In 2011, Goodwin hired Indiana attorneys Clark W. Holesinger and DeBoer 

and Texas attorney William E. Kelly III to represent him in a federal criminal 

action for alleged Medicaid fraud in Texas. In May of 2012, Holesinger and 

DeBoer retained a Medicaid expert, Christine Miller, who authored a draft 

report on Goodwin’s alleged fraud.

[3] In December, Goodwin entered into a written plea agreement with the United 

States. Pursuant to his plea agreement, Goodwin agreed to plead guilty to one 

count of health care fraud, and, in exchange, the United States dismissed eleven 

other counts. At a hearing on Goodwin’s guilty plea, Goodwin acknowledged 

as true a “factual resume” that established a factual basis for the offense. 

Appellant’s App. Vol. 3 at 126-31, 177. On several occasions, the court asked 

Goodwin if he had reviewed his plea agreement and decision to plead guilty 

with his attorneys. Goodwin repeatedly affirmed that he had done so. With 
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respect to the factual resume in particular, Goodwin stated that he had “gone 

over it completely” with his attorneys “[m]any times.” Id. at 177-78. The court 

entered its judgment of conviction against Goodwin and sentenced him to fifty 

months with the Federal Bureau of Prisons.

[4] Thereafter, in April of 2014 the Porter County Prosecutor alleged that 

Holesinger “stole approximately $380,000.00 from Dr. Michael Goodwin and 

his wife . . . during the time he represented Dr. Goodwin for Medicaid fraud.” 

Appellant’s App. Vol. 12 at 76. Holesinger surrendered his Indiana law license 

and pleaded guilty to several federal and state crimes. However, despite the 

Porter County Prosecutor’s allegation, none of Holesinger’s convictions directly 

related to funds allegedly stolen from Goodwin.

[5] Shortly after learning of Holesinger’s conduct, Goodwin moved to have the 

district court set aside his guilty plea on the basis that Holesinger had rendered 

ineffective assistance, which motion Goodwin later amended. In relevant part, 

Goodwin’s amended motion argued that Holesinger had advised him to plead 

guilty, and Goodwin had acted on that advice, while Holesinger “was burdened 

by an actual conflict of interest . . . due to his theft of approximately [$380,000] 

from Goodwin during his representation . . . .” Appellant’s App. Vol. 11 at 

135. Goodwin further alleged that Holesinger’s advice was ineffective because 

Holesinger had “concealed the Miller Report” from Goodwin, which Goodwin 

argued was “favorable and necessary for Goodwin’s defense.” Id. at 142-43. In 

other words, Goodwin argued that, had he known of Holesinger’s conduct 
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and/or the Miller report, he would not have pleaded guilty. See Appellant’s 

App. Vol. 12 at 122.

[6] The district court set a hearing date on Goodwin’s amended motion. Ten days

before that hearing, in June of 2016, DeBoer sent to Goodwin’s wife a draft 

statement for the court on Goodwin’s behalf, which statement Goodwin’s wife 

“immediately” surrendered to Goodwin’s acting counsel. Id. at 96-97. In that 

statement, DeBoer said:

It seems almost [a] foregone conclusion to me that if Clark 

Holesinger was stealing from Michael Goodwin while 

representing him in the Medicaid case, Goodwin did not have 

the benefit of appropriate[,] competent representation.

Did Holesinger steal from Goodwin? In my opinion, it is far 

more probable than not that he did.

I come to that conclusion by recalling my observations of 

Holesinger during the months I helped him with the Goodwin 

case. The nature of the federal Medicaid fraud case meant not 

only did [Goodwin] face criminal penalties for [the] alleged 

violations, he also was at risk to lose all or a large part of his 

substantial net worth. Bank accounts were frozen, real estate was 

attached. During visits to his office, I overheard Holesinger’s 

portion of phone conversations cutting deals with bankers in 

charge of Goodwin’s holdings. There was also a stylish RV that 

was pursued by the government. I believe Holesinger sold this 

for cash . . . before it was seized.

[Holesinger] appeared more motivated and energized to work on 

the civil/financial aspects of the government’s case than the 

criminal case proper.
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Id.

[7] Nearly eleven months after the evidentiary hearing, the district court’s 

magistrate judge issued his report and recommendation to deny Goodwin’s 

amended motion to set aside his guilty plea. In relevant part, the magistrate

judge found as follows:

In this case, the criminal acts committed by GOODWIN’s 

Indiana counsel, Mr. Holesinger, require the Court to carefully 

and stringently consider this claim and whether counsel’s illegal 

activities affected GOODWIN’s plea and whether such impacted 

GOODWIN’s decision to accept a guilty plea. . . .

* * *

GOODWIN’s claim that his guilty plea was unintelligent and 

involuntary is conclusory and does not set forth specific factual 

allegations to amount to a constitutional violation. His claims in 

his Amended Motion to Vacate . . . are not supported by reliable 

evidence and these claims contradict the statements GOODWIN 

made in his plea agreement and in open court at his 

rearraignment. . . .

GOODWIN also claimed Mr. Holesinger told him that he had 

insufficient funds to put forth a defense at trial, and it was this 

information that led GOODWIN to accept a plea of guilty. 

However, GOODWIN was advised of his right to have 

appointed counsel at any time throughout his proceedings if he 

could no longer afford retained counsel or if a conflict arose and 

he could not afford separate counsel. Additionally, the record 

reflects GOODWIN’s decision to plead guilty was a result of the 

plea agreement deadline to dismiss charges against his wife and 

office manager, not because of a lack of funds to proceed to trial. 
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In a letter after his sentencing, GOODWIN stated that he 

accepted a guilty plea because he feared the prosecutor would 

proceed with charges against [Mrs. Goodwin] and [the office 

manager] and he wanted to “save them.”

* * *

The evidence presented at the evidentiary hearing and from 

documents of record in this case indicate that GOODWIN’s 

attorney, Mr. Holesinger, was convicted of Wire Fraud and Theft 

from a pattern of stealing and/or embezzling from his clients. 

This is not disputed by the government and in fact, Mr. 

Holesinger appeared at the evidentiary hearing . . . . However, 

evidence presented at the evidentiary hearing was inadequate to show 

what amount, if any, Mr. Holesinger might have stolen or embezzled 

from GOODWIN. Although GOODWIN testified and presented 

records that he paid Mr. Holesinger approximately $400,000 over 

the course of the representation, GOODWIN has not established 

what amounts of money did not go to legitimate representation 

fees. In fact, it appears GOODWIN is claiming Mr. Holesinger 

embezzled approximately $380,000, meaning that GOODWIN 

believes less than $20,000 was spent on the defense of a 

complicated Medicaid Fraud case spanning over a year and a 

half. The evidentiary hearing record shows Mr. Holesinger 

provided legitimate legal services to GOODWIN. He hired an 

expert, Ms. Miller, hired co-counsel, Mr. DeBoer, hired local 

counsel, William E. Kelly III, and traveled and investigated this 

case, and continued to provide representation from the date he 

was retained in mid-2012 through sentencing in April of 2013. 

Thus, GOODWIN has failed to show Mr. Holesinger actually 

embezzled from him, or, if he did, the amount Mr. Holesinger embezzled. 

GOODWIN certainly has established Mr. Holesinger’s bad acts 

against other clients but at most, he has only shown Mr. 

Holesinger might have stolen from GOODWIN. In any event, 

GOODWIN has failed to meet his burden to show that such behavior 

resulted in deficient performance of counsel and has further failed to prove 
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how the deficient performance prejudiced GOODWIN’s criminal case. 

Mr. Holesinger’s conduct in defrauding other clients undermines 

confidence in the legal system and calls into question the 

representation provided by Mr. Holesinger to GOODWIN. The

Court considers Mr. Holesinger’s behavior reprehensible and has 

nothing positive to say about it. However, the burden remains 

on GOODWIN to show both an actual deficient performance 

and resulting prejudice and the Court cannot impute the 

dishonesty of Mr. Holesinger in stealing from other clients to his 

representation of GOODWIN. It is GOODWIN’s task to show 

prejudice by showing specific actions taken or not taken by Mr. 

Holesinger which would have altered the outcome or altered 

GOODWIN’s decision to plead guilty. For example, 

GOODWIN did not show that the alleged embezzlement caused 

Mr. Holesinger to fail to hire an expert and that such failure 

would have changed the course of his case. This high burden 

falls on GOODWIN despite Mr. Holesinger’s clearly egregious 

behavior that GOODWIN became aware of after-the-fact of the 

plea and sentencing and which has undermined GOODWIN’s 

confidence in Mr. Holesinger’s representation. GOODWIN, 

throughout his Motion to Vacate and his evidentiary hearing, 

argued that his attorney, Mr. Holesinger, was convicted of 

wrongdoing in the handling of client funds. GOODWIN then 

leaps to the conclusion that this wrongdoing resulted in per se 

deficient performance in GOODWIN’s representation which 

also resulted in per se prejudice in GOODWIN’s criminal case. 

This automatic leap from proving an attorney’s wrongdoing or 

criminal behavior to proving deficient performance and prejudice 

is misguided. Proving breach of the standard of care owed to a 

client and proving deficient performance are not identical 

processes or findings, nor is proving actual prejudice identical.

* * *

. . . [D]espite his conclusory claims that he would have “insisted 

on a trial,” he has failed to show such an insistence would have 
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been rational. He testified at the evidentiary hearing that “he 

wouldn’t continue with someone stealing from me” if he had 

known about the alleged theft/embezzlement during the 

representation. As set out above, however, he never established 

whether or what amount of funds were misappropriated. Mr. 

Holesinger’s conviction documents . . . did not include charges 

that Mr. Holesinger misappropriated funds from GOODWIN 

and to the Court’s knowledge GOODWIN was never named as a 

victim in a criminal case filed against Mr. Holesinger. 

GOODWIN must offer more than he has to establish that he has 

met the prejudice showing required . . . . Furthermore, he has 

failed to meet his burden to show these alleged constitutional 

violations even occurred, because they are contradicted by earlier 

statements made by GOODWIN and no supporting 

documentary evidence or testimony corroborates GOODWIN’s 

change of testimony.

* * *

GOODWIN gave conflicting testimony and statements regarding 

the Miller report. He acknowledged at one point that he had 

discussed it with [Holesinger] prior to his plea and was told the 

Miller report was not favorable to his case. He later claimed he 

did not know about the report until after his sentencing. . . . [T]o 

the extent that [the Miller report] relates generally to the claim 

that Mr. Holesinger failed to investigate possible defenses, 

GOODWIN has failed to show prejudice by articulating what 

defenses GOODWIN had to the allegations in the superseding 

indictment and how Mr. Holesinger’s alleged deficient 

performance affected the outcome of his guilty plea. 

Furthermore, no argument was made as to what specific information 

was contained in the report that would have been a rational basis for 

GOODWIN to insist upon a trial, rather than pleading guilty. Ms. 

Miller could have been subpoenaed to testify at the evidentiary 

hearing if she had specific information regarding a viable defense 

for GOODWIN’s case.
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Id. at 116, 118-23, 129 (emphases added; citations omitted). The district court 

then adopted the magistrate’s findings and entered judgment against Goodwin.

[8] In February of 2017, Goodwin filed suit against DeBoer in the Lake Superior 

Court. Goodwin’s complaint alleged that DeBoer had committed legal 

malpractice, breach of fiduciary duty, and fraudulent concealment. According 

to his complaint, Goodwin learned of DeBoer’s misconduct from DeBoer’s 

June 2016 statement to the district court in support of Goodwin’s amended 

motion to vacate his guilty plea. In particular, Goodwin alleged that DeBoer 

had breached his duty of care to Goodwin when:

a. During visits to Clark Holesinger’s office, [DeBoer] 

“overheard Holesinger’s portions of phone conversations cutting 

deals with bankers in charge of Goodwin’s holdings.”

b. [DeBoer] was aware [Goodwin] owned a stylish RV that 

was pursued by the government. [DeBoer] believes “Holesinger 

sold the RV for cash . . . before it was seized.”

c. [DeBoer] observed “Clark Holesinger appeared more 

motivated and energized to work on the civil/financial aspects of 

the government’s case than the criminal case proper.”

Appellant’s App. Vol. 2 at 20. Goodwin further alleged that DeBoer failed to 

“disclose the Medicaid expert’s draft report to [Goodwin],” which report he 

generically alleged “supported a very strong defense.” Id. at 21. Because of 

DeBoer’s alleged misconduct, Goodwin continued, Goodwin “was unable to 

make an informed decision regarding the outcome of his case” and he “would 
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not have ple[aded] guilty . . . .” Id. at 19, 24. That is, Goodwin alleged only 

that, but for DeBoer’s alleged malpractice, the outcome of the federal criminal 

action would have been different. In due course, DeBoer moved for summary 

judgment, which the trial court granted. This appeal ensued.

Discussion and Decision

[9] Goodwin appeals the trial court’s entry of summary judgment for DeBoer. As 

our Supreme Court has stated:

This Court reviews summary judgment orders de novo. Summary 

judgment is appropriate if the designated evidence shows there is 

no genuine issue as to any fact material to a particular issue or 

claim, and the moving party is entitled to judgment as a matter of 

law. In viewing the matter through the same lens as the trial 

court, we construe all designated evidence and reasonable 

inferences therefrom in favor of the non-moving party. Legal 

questions, such as contract interpretation, are well-suited for 

summary judgment. The party appealing the trial court’s 

summary judgment determination bears the burden of persuading 

us the ruling was erroneous. Nonetheless, we “carefully 

scrutinize[] the trial court’s decision to assure that the party 

against whom summary judgment was entered was not 

improperly prevented from having its day in court.”

Ryan v. TCI Architects/Engineers/Contractors, Inc., 72 N.E.3d 908, 912-13 (Ind. 

2017) (citations omitted; alteration original to Ryan). Further, “we may affirm 

a grant of summary judgment upon any theory supported by the evidence.” 

Miller v. Danz, 36 N.E.3d 455, 456 (Ind. 2015).
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[10] Although Goodwin’s complaint alleges three claims, the essence of his 

complaint is that DeBoer committed legal malpractice when DeBoer did not 

inform Goodwin of Holesinger’s purported misappropriation of funds and also 

when DeBoer did not share the Miller report with Goodwin. A claim of legal 

malpractice invokes the “trial-within-a-trial” doctrine, under which

a client alleging legal malpractice must prove not only that the 

lawyer’s conduct fell below the governing duty of care but also 

that the client would have prevailed had the lawyer not been 

negligent . . . .

* * *

To prevail on [a] legal malpractice claim . . . , [the client] has to 

prove three things: (1) She retained the firm to represent her 

legal interests, so that the firm owes her a duty of care; (2) the 

firm breached its duty of care by failing to exercise the ordinary 

skill and knowledge expected of lawyers; and (3) the firm’s 

breach was the proximate cause of [the client’s] injury. . . .

. . . [U]nder the [“trial-within-a-trial”] doctrine, the client must 

show the outcome of the botched representation would have been more 

favorable to the client had the lawyer not been negligent. In other words, 

the client must prove the lawyer’s negligence proximately caused her 

injury. . . .

Roumbos v. Vazanellis, 95 N.E.3d 63, 64-66 (Ind. 2018) (emphasis added). In 

legal malpractice actions, the proximate causation requirement is a “but for” 

requirement. See, e.g., Richard H.W. Maloy, Proximate Cause: The Final Defense 

in Legal Malpractice Cases, 36 U. Mem. L. Rev. 655, 671-77 (2006). That is, the 
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client-plaintiff must show that, had the attorney-defendant not acted as he did, 

the result of the underlying lawsuit would have been different. Id. 

[11] In his complaint, Goodwin alleged that, but for DeBoer’s alleged misconduct, 

he would not have pleaded guilty in the federal criminal action. In his motion 

for summary judgment, DeBoer argued that Goodwin in effect seeks to 

relitigate the ineffective assistance of counsel claim he made in the district court 

against Holesinger, which is not permitted. See, e.g., Williams v. Maschmeyer, 

870 N.E.2d 1069, 1070 (Ind. Ct. App. 2007) (“under Indiana precedent, a postconviction finding that counsel was not ineffective provides the necessary 

identity of issues to preclude a malpractice action stemming from the same 

proceedings.”) (brackets and quotation marks omitted). That is, DeBoer argued 

that the district court had already heard and found that Goodwin had failed to 

show that Holesinger had rendered ineffective assistance to Goodwin with 

respect to Holesinger’s misappropriation of funds and also with respect to

informing Goodwin of the Miller report. DeBoer asserted that Goodwin’s 

complaint here was ultimately about those same issues. The trial court agreed, 

and so do we.

[12] As we have explained:

Issue preclusion[, also known as collateral estoppel,] bars the 

subsequent litigation of a fact or issue that was necessarily 

adjudicated in a former lawsuit if the same fact or issue is 

presented in the subsequent lawsuit. If issue preclusion applies, 

the former adjudication is conclusive in the subsequent action, 

even if the actions are based on different claims. The former 
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adjudication is conclusive only as to those issues that were 

actually litigated and determined therein. Thus, issue preclusion 

does not extend to matters that were not expressly adjudicated 

and can be inferred only by argument. In determining whether 

issue preclusion is applicable, a court must engage in a two-part 

analysis: (1) whether the party in the prior action had a full and 

fair opportunity to litigate the issue, and (2) whether it is 

otherwise unfair to apply issue preclusion given the facts of the 

particular case. The non-exhaustive factors to be considered by 

the trial court in deciding whether to apply issue preclusion 

include: (1) privity, (2) the [party’s] incentive to litigate the prior 

action, and (3) the ability of the [party] to have joined the prior 

action.

Angelopoulos v. Angelopoulos, 2 N.E.3d 688, 696 (Ind. Ct. App. 2013), trans. 

denied.

[13] The district court’s judgment against Goodwin on his motion to vacate his 

guilty plea conclusively established that Goodwin did not show that 

Holesinger’s misappropriation of funds (against clients other than Goodwin)

affected his representation of Goodwin or that Goodwin would not have 

pleaded guilty had he known of Holesinger’s misconduct. It further 

conclusively established that Goodwin had failed to carry his burden to show 

that, had he known of the Miller report, he would not have pleaded guilty. The 

district court’s judgment in both respects precludes Goodwin from relitigating 

those issues here. See id.; Williams, 870 N.E.2d at 1070.

[14] Thus, the designated evidence demonstrates as a matter of law that Goodwin 

cannot show that DeBoer’s alleged misconduct would have resulted in a 

different outcome. DeBoer’s alleged misconduct is simply a failure to inform 
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Goodwin of Holesinger’s misconduct and the Miller report, but the district 

court has already expressly found that Goodwin did not adequately show that 

he would not have pleaded guilty had he known of Holesinger’s misconduct or 

the Miller report. See Sullivan v. Am. Cas. Co., 605 N.E.2d 134, 139 (Ind. 1992) 

(holding that “identity of parties” is not required “for the defensive use of 

collateral estoppel”). Goodwin’s claim against DeBoer is derivative of his 

claim against Holesinger. Because his claim against Holesinger has been 

adjudicated, his collateral claim against DeBoer must also fail.

[15] Nonetheless, Goodwin argues1that it would be unfair to apply issue preclusion 

against him because the United States Court of Appeals for the Fifth Circuit has 

agreed to review part of the district court’s denial of his motion to vacate his 

guilty plea.2 But the Fifth Circuit’s certificate of appealability is expressly 

limited to the issue of whether Holesinger rendered ineffective assistance when 

he failed to appear at Goodwin’s guilty plea hearing. That issue is not relevant 

to our appeal. We reject Goodwin’s argument that it would be unfair to apply 

issue preclusion on these facts.

[16] In sum, the designated evidence shows that no genuine issue of material fact 

exists on the question of proximate causation, which underlies each of 

 

1

 We agree with DeBoer that much of Goodwin’s purported arguments on appeal are “so cursory [as] to 

defy the cogent argument rule.” Appellee’s Br. at 32; see Ind. Appellate Rule 46(A)(8)(a).

2

 We take judicial notice of the Fifth Circuit’s order. We also note that Goodwin does not argue that the 

Fifth Circuit’s decision to review part of the district court’s judgment renders the remainder of that judgment 

nonfinal.
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Goodwin’s claims against DeBoer. Thus, DeBoer is entitled to judgment as a 

matter of law, and we affirm the trial court’s entry of summary judgment for 

DeBoer accordingly.

[17] Affirmed.

Crone, J., and Pyle, J., concur.