United States v. Bray

United States Court of Appeals
For the First Circuit

No. 16-1579

UNITED STATES OF AMERICA,

Appellee,

v.

ROBERT H. BRAY,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS

[Hon. William G. Young, U.S. District Judge]

Before

Howard, Chief Judge,
Souter, Associate Justice,*
and Stahl, Circuit Judge.

Mark C. Fleming, with whom Emily R. Schulman, Matthew T.
Martens, Daniel Winik, Alan E. Schoenfeld, Wilmer Cutler Pickering
Hale and Dorr LLP, Joseph W. Monahan III, and Monahan & Padellaro
were on brief, for appellant.
Eric P. Christofferson, Assistant United States Attorney,
with whom Stephen E. Frank, Assistant United States Attorney, and
William D. Weinreb, Attorney for the United States, were on brief,
for appellee.

* Hon. David H. Souter, Associate Justice (Ret.) of the
Supreme Court of the United States, sitting by designation.
February 24, 2017
 STAHL, Circuit Judge. In what appears to be an ongoing

trend, we again encounter a member of the Oakley Country Club

("Oakley"), a private institution located in Watertown,

Massachusetts, answering to criminal securities fraud charges.1

On this occasion, a jury convicted Robert Bray of illegal insider

trading after he received material, nonpublic information about a

local bank from a fellow Oakley member and then used that

information to make a substantial trading profit. On appeal, Bray

insists that we set aside his conviction because the government

presented insufficient evidence to support the jury’s verdict.

Bray also maintains that the trial court's instructions allowed

the jury to convict him without finding that he possessed the

necessary mental state. See 15 U.S.C. § 78ff(a) (requiring the

government to prove that a defendant "willfully" violated the

securities laws in order to sustain a criminal conviction). After

careful review, we reject Bray's arguments and affirm his

conviction.

I. Facts & Background

We recite the facts in the light most favorable to the

jury's verdict, "reserving the detailed treatment of some points

for later in this opinion.” McPhail, 831 F.3d at 3. Bray and

1
We have previously dealt with two criminal insider trading
actions involving individuals belonging to the same country club.
See United States v. McPhail, 831 F.3d 1 (1st Cir. 2016); United
States v. Parigian, 824 F.3d 5 (1st Cir. 2016).

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John Patrick O'Neill first met each other as members at Oakley, a

private establishment that provides tennis, swimming, golf, and

other social activities to its members. Though the disparity in

their respective golf skills meant Bray, a contractor and real-

estate developer, and O'Neill, an executive at Eastern Bank

("Eastern"), rarely played together, the two men often socialized

with each other in Oakley’s pub room and dined on occasion with

one another at nearby bars and restaurants. Over time, Bray (or

"Bubba," as O'Neill called him) got to know O'Neill's family as

well. He took a particular liking to O'Neill's son, Matthew; for

example, Bray gifted Matthew his first set of golf clubs as a

child, attended his high school graduation party at O'Neill's

house, and gave him a $1,000 check as a graduation present. Bray

later helped Matthew get an internship with an architect, hired

Matthew to prepare architectural drawings for one of his own real-

estate projects, and served as a reference when Matthew applied

for a job at a restaurant.

Though Bray and O'Neill generally maintained a social

relationship, the pair's discussions occasionally drifted toward

their professional lives. O'Neill, for instance, had some of

Bray's associates refurbish the basement and roof at his house,

while Bray often asked O'Neill for stock market and investment

advice. In particular, Bray leaned on O’Neill’s professional

experience and regularly asked him about “what bank stocks [he]

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liked.” O'Neill always answered these questions by advising Bray,

based on publicly-available information, to invest in small

community banks that were likely merger or take-over targets.

On June 13, 2010, however, O’Neill and Bray had a

decidedly different conversation. While they were sitting

together in the Oakley pub room, just the two of them, Bray said

to O'Neill that he needed to make a "big score" in order to help

fund one of his real estate projects (the "Watertown Project") and

asked if O'Neill had any "bank stock tips" for him. According to

O'Neill, Bray had never sought a "big score" from him before or,

for that matter, requested advice based on an express need for

money. O'Neill, as he had done in the past, rattled off the names

of several local banks. However, this time O’Neill also took a

napkin, penned the word "Wainwright" on it, and slid it across the

bar toward Bray. As he did so, O'Neill told Bray that "[t]his

could be a good one," or at least "something to that effect." Bray

wordlessly took the napkin, slipped it into his pocket, and did

not mention or ask about its contents for the rest of the night.

At the time, O'Neill knew that Wainwright Bank & Trust

Co. ("Wainwright"), a local, publicly-traded bank, had put itself

up for sale. This information was nonpublic and Eastern, O'Neill's

employer, had told O'Neill to perform due diligence on Wainwright

since it was a potential takeover candidate. Before starting that

task, O'Neill had signed an agreement with Eastern that required

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him to keep any nonpublic information he learned about Wainwright

confidential. O'Neill did not explicitly inform Bray about this

agreement or the source of his Wainwright tip.

When queried at trial as to why he had given Bray this

tip, O'Neill answered:

I don't know to this day, although I did want to
help out Mr. Bray, he had done stuff for me in the
past and for my family and here was an opportunity
for me to return the favor. I looked up to Mr.
Bray and I figured that doing this would enhance
our relationship, he would think more highly of me.

Then, when questioned about whether he expected Bray to

"return the favor" someday, O'Neill replied:

Well, we're friends and that's what friends do,
they take care of each other. I didn't expect
anything at that exact time, but down the road he
did offer me an interest in the Watertown project.

The day after receiving the tip, Bray called his broker,

E*Trade, to place an order for 25,000 shares of Wainwright stock.

Evidence at trial suggested that the size of Bray's trade was most

unusual, as at the time of Bray's order, Wainwright was a "thinly-

traded" stock with an average daily trading volume of around 1,000

to 2,000 shares. When an E*Trade representative pointed out

Wainwright's relative illiquidity, Bray acknowledged that the

trade might be "crazy." Nonetheless, Bray proceeded to place the

order, though the broker did manage to convince him to structure

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the trade as a limit order2 which spread the trade’s execution over

multiple days. Over the next two weeks, Bray did two things.

First, he liquidated a vast portion of his existing portfolio,

generating approximately $555,000. Second, he bought 31,000

Wainwright shares, which amounted to 56% of the stock's total

trading volume between June 14th and June 28th. By that point,

Wainwright shares comprised around 57% of Bray's securities

portfolio.

On June 29, 2010, Eastern publicly announced an

agreement to acquire Wainwright for $19 per share, almost double

the previous day’s closing price. After the announcement, Bray

met O'Neill in the Oakley parking lot, thanked him for the tip,

and offered to "bring [O'Neill] into the Watertown project."

Although Bray had never previously offered O'Neill an opportunity

to invest in any of his real-estate projects, O'Neill nevertheless

declined the invitation on this first opportunity. When Bray sold

his shares under the terms of the acquisition agreement in November

2010, he netted approximately $300,000.

Before Bray sold his shares, O'Neill received an email

from Eastern's legal department stating that the Financial

Industry Regulatory Authority ("FINRA"), a non-governmental

2
"A 'limit order' is an order to buy or sell [a security] at
a specified price in contrast to a 'market order' to buy or sell
at the prevailing price." Belenke v. SEC, 606 F.2d 193, 195 (7th
Cir. 1979).

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organization that regulates professionals and firms in the

securities industry, had initiated an investigation into the

trading activity in Wainwright stock that occurred immediately

before the June 29th announcement. A list of individuals and

companies accompanied the investigatory notice. FINRA asked

Eastern to circulate the list to its officers and directors; if

any Eastern officer or director recognized a name on the list,

FINRA requested that the bank advise it of the nature of the

relationship between the employee and the listed name. FINRA also

asked that the bank tell it whether any communications among those

parties had taken place before the Wainwright announcement.

Seeing Bray's name on the list, O'Neill panicked and

rushed to Oakley to look for him. On finding Bray, O'Neill

stressed that he could "lose [his] job over this." Bray tried to

calm O'Neill down by assuring O'Neill that he had not "told

anybody" about the tip and that "if the regulators c[a]me around

asking questions," he would "have them wishing that they had bought

[Wainwright] stock."3

On August 18, 2014, the Securities and Exchange

Commission ("SEC") filed a civil insider trading action against

O'Neill and Bray. Bray initially filed a pro se answer where he

3 Bray again offered to include O'Neill in the Watertown
Project, this time for free. Because Bray and his business
partners ultimately abandoned the Project, the offer never bore
fruit.

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denied receiving "any 'tip' from O'Neill," and later insisted in

his answers to the SEC's first set of interrogatories that he had

bought Wainwright shares because of the bank's environmentally-

friendly policies and good dividends. He later admitted that both

these things were untrue, but asserted that O'Neill had passed him

the Wainwright tip unprompted.

On December 10, 2014, the government charged Bray with

criminal securities fraud in violation of 15 U.S.C. §§ 78j(b) and

78ff(a), and conspiracy to commit securities fraud in violation of

18 U.S.C. § 371. At the close of his trial, the district court

instructed the jury on the elements of both offenses. As relevant

here, the court told the jury that in order to convict Bray of

securities fraud, it needed to find that he "knew or under all the

circumstances . . . should have known" that O'Neill had breached

a duty of confidentiality by giving him the Wainwright tip.

Alternatively, the district court told the jury that it could find

that Bray possessed the requisite knowledge if he had willfully

blinded himself to O'Neill's breach; that is, if "under all the

circumstances . . . a reasonable person in Mr. Bray's shoes would

certainly have known that this information was being passed to

him" in violation of a duty of confidentiality.

On January 28, 2016, the jury convicted Bray of

committing securities fraud, but acquitted him of the conspiracy

charge. The district court then sentenced Bray to 24 months in

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prison, followed by 36 months of supervised release, and imposed

a $1 million fine.

II. Discussion

The unlawful trading in securities based on material,

nonpublic information, or illegal insider trading, is a well-

established violation of Section 10(b) of the Securities Exchange

Act of 1934 and the Securities and Exchange Commission's Rule 10b-

5. See United States v. Salman, 137 S. Ct. 420, 423 (2016); United

States v. O'Hagan, 521 U.S. 642, 652 (1997); Dirks v. SEC, 463

U.S. 646, 653-54 (1983); Chiarella v. United States, 445 U.S. 222,

226-30 (1980); SEC v. Texas Gulf Sulphur Co., 401 F.2d 833, 847-

48 (2d Cir. 1968) (en banc). In this case, the government premised

Bray's prosecution on the "misappropriation" theory of insider

trading liability. This theory posits that individuals entrusted

with confidential information about a corporation cannot "secretly

us[e] such information for their personal advantage," even when

they do not owe any direct fiduciary duty to that corporation or

its shareholders. Salman, 137 S. Ct. at 423. Instead, those

entrusted with such information have a duty to abstain from trading

in that corporation's securities or they must disclose the

information ahead of time. Id. Thus, these individuals "commit[]

a fraud 'in connection with' a securities transaction, and thereby

violate[] § 10(b) and Rule 10b-5, when [they] misappropriate[]

confidential information for securities trading purposes, in

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breach of a duty to the source of the information.” O'Hagan, 521

U.S. at 652.

The misappropriation theory "can also apply when the

misappropriator does not trade, but instead obtains a benefit by

revealing the information to a third person who trades based on

the misappropriated information." McPhail, 831 F.3d at 4. In

these "tipping" situations, the third person, or “tippee,”

inherits the misappropriator’s, or “tipper's,” abstain-or-disclose

duty "if the tippee knows the information was disclosed in breach

of the tipper's duty" and "may commit securities fraud by trading

in disregard of that knowledge." Salman, 137 S. Ct. at 423.

Liability therefore hinges on whether the tipper breached a duty

of trust and confidence by disclosing the inside information, which

in turn depends on whether the tipper "personally will benefit,

directly or indirectly, from [the] disclosure." Dirks, 463 U.S.

at 662; see also Parigian, 824 F.3d at 15 (stating that the

personal benefit analysis "seem[s] to call for the same answer in

both a civil and criminal proceeding").4

4
The Supreme Court has developed the tipping liability
doctrine, including its personal benefit requirement, under the
"classical" theory of insider trading liability. Dirks, 463 U.S.
at 646; see also O'Hagan, 521 U.S. at 651-52 (stating that, in a
classical case, "§ 10(b) and Rule 10b-5 are violated when a
corporate insider trades in the securities of his corporation on
the basis of material, nonpublic information"). However, we have
previously acknowledged that "[t]here is some disagreement about
whether benefit to a . . . tipper is a required element of"
liability under the misappropriation theory. SEC v. Sargent, 229

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 Bray admits that he traded based on material, nonpublic

information about Wainwright, that O'Neill owed Eastern a "duty of

loyalty and confidentiality," O'Hagan, 521 U.S. at 652, and that

O'Neill breached this duty by giving the Wainwright information to

him. Still, Bray maintains that the government presented

insufficient evidence proving that O'Neill expected a personal

benefit in exchange for the Wainwright tip, that he knew O'Neill

anticipated such a benefit in exchange for the tip, or that he

knew O'Neill had breached a fiduciary duty by giving him the tip.

Bray also insists that the trial court plainly erred by instructing

the jury that it could convict him if he "should have known" that

O'Neill had an obligation to keep the Wainwright information

confidential. He similarly claims that the trial court wrongly

equated the concept of "willful blindness," an alternative theory

on which the government could prove Bray’s knowledge, with

negligence. We address each argument in turn.

A. Sufficiency of the Evidence Claims

This court reviews sufficiency of evidence challenges de

novo. United States v. García-Carrasquillo, 483 F.3d 124, 129-30

F.3d 68, 77 (1st Cir. 2000); see also Parigian, 824 F.3d at 15
(acknowledging disagreement); SEC v. Rocklage, 470 F.3d 1, 7 n.4
(1st Cir. 2006) (same). We do not need to resolve that
disagreement here since, as we will explain, there was enough
evidence such that a reasonable jury could conclude beyond a
reasonable doubt that O'Neill disclosed the Wainwright tip in
expectation of a personal benefit.

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(1st Cir. 2007). While doing so, we draw all reasonable inferences

in the verdict’s favor. United States v. Alejandro-Montañez, 778

F.3d 352, 357 (1st Cir. 2015). Thus, "[i]f a reasonable jury could

find the defendant[] guilty beyond a reasonable doubt of all

elements of the charged offense, we must affirm the conviction."

United States v. Rosado-Pérez, 605 F.3d 48, 52 (1st Cir. 2010).

"[D]efendants challenging the sufficiency of the evidence face 'an

uphill battle.'" United States v. Manso-Cepeda, 810 F.3d 846, 849

(1st Cir. 2016) (quoting United States v. Seng Tan, 674 F.3d 103,

107 (1st Cir. 2012)). This battle, as it turns out, Bray cannot

win.

1. O'Neill's Tipping Motivations

To start, O'Neill's trial testimony provided a

sufficient basis for the jury to infer that O'Neill gave Bray the

Wainwright tip with the "purpose" of obtaining a personal benefit.

See Dirks, 463 U.S. at 662. When evaluating whether a tipper

derived a personal benefit from his or her tip, we "focus on

objective criteria, i.e., whether the insider receives a direct or

indirect personal benefit from the disclosure, such as a pecuniary

gain or a reputational benefit that will translate into future

earnings." Id. at 663. However, a personal benefit can “often”

be inferred where "a relationship between the [tipper] and the

recipient . . . suggests a quid pro quo from the latter, or an

intention to benefit the particular recipient." Id. at 664; see

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also Sargent, 229 F.3d at 77 ("The 'benefit' to the tipper need

not be 'specific or tangible.'" (quoting SEC v. Warde, 151 F.3d

42, 48-49 (2d Cir. 1998)). A personal benefit can likewise be

inferred where a tipper makes a gift of "inside information to 'a

trading relative or friend.'" Salman, 137 S. Ct. at 428 (quoting

Dirks, 463 U.S. at 664); see also Rocklage, 470 F.3d at 7 n.4

(stating that "the mere giving of a gift to a relative or friend

is a sufficient personal benefit").

Bray argues that an informational exchange between

casual, as opposed to close, friends does not meet Dirks's personal

benefit requirement without some other evidence of a quid pro quo

exchange.5 Here, Bray claims that the evidence at trial did not

establish either that he and O'Neill enjoyed a close relationship

or that O'Neill gave him the Wainwright advice as a quid pro quo

in expectation of a future benefit. These arguments, however,

5 His argument stems from the Second Circuit's decision in
United States v. Newman, where that court held that it could not
infer a personal benefit "in the absence of proof of a meaningfully
close personal relationship that generates an exchange that is
objective, consequential, and represents at least a potential gain
of a pecuniary or similarly valuable nature." 773 F.3d 438, 452
(2d Cir. 2014). The Supreme Court abrogated the latter half of
this holding in Salman, rejecting any requirement "that the tipper
. . . receive something of a 'pecuniary or similarly valuable
nature' in exchange for a gift to family or friends." 137 S. Ct.
at 428 (quoting Newman, 773 F.3d at 452). Salman did not, however,
discuss the Second Circuit's "meaningfully close personal
relationship" language, presumably because the tipper in the case
"provided inside information to a close relative," namely "his
brother." Id. at 427. Consequently, Salman does not foreclose
Bray's argument.

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amount to an attack on the credibility of the witnesses who

testified against him. As we have often stated, "it is not the

appellate court's function to weigh the evidence or make

credibility judgments." E.g., United States v. Ortiz, 966 F.2d

707, 711 (1st Cir. 1992). Instead, we leave it to "the jury to

choose between varying interpretations of the evidence." Id.; see

also Alejandro-Montañez, 778 F.3d at 357 ("Testimony from even

just one witness can support a conviction." (internal quotation

marks and citation omitted)).

To that end, O'Neill's testimony showed that it is at

least "plausible" that he and Bray had a close relationship. See

Ortiz, 966 F.2d at 711. O'Neill claimed that he and "Bubba" were

"good friends" who, at the time of the Wainwright tip, had known

each other for fifteen years. The two men often socialized with

each other at the club, dined with each other at local bars and

restaurants, and even took each other's counsel. Bray's bond with

Matthew, O'Neill's son, similarly demonstrated that Bray knew

O’Neill well enough to extend favors to O’Neill’s extended family.

In other words, the government presented enough evidence for a

reasonable jury to conclude that Bray and O'Neill had a close

relationship, and not one that was "of a casual or social nature."

Newman, 773 F.3d at 452; see also Sargent, 229 F.3d at 77

(concluding that there was sufficient evidence from which a jury

could conclude that a tipper benefitted by tipping, in part because

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the tipper and tippee were "friendly," had done favors for each

other in the past, and enjoyed relationships with one another's

extended families).

O'Neill's testimony also provided a sufficient basis for

the jury to conclude that he disclosed the tip in expectation of

a personal benefit. Though O'Neill initially testified that he

did not know why he had given Bray the Wainwright tip, he then

immediately said that he "figured [the tip] would enhance" his

reputation with Bray. While O'Neill "did not expect anything at

the exact time" he gave Bray the tip, a reasonable jury could infer

that he expected a benefit "down the road." See United States v.

Riley, 90 F. Supp. 3d 176, 184 (S.D.N.Y. 2015) ("The precise

exchange need not be known by the parties at the time of the

tip."), aff'd, 638 F. App'x 56 (2d Cir. 2016), cert. denied 137 S.

Ct. 589 (2016). Bray's later offers to bring O'Neill into the

Watertown Project for free further show that these expectations

were warranted.

It bears emphasizing that our holding on this front is

a narrow one. We need not determine, for instance, how "close" a

tipper-tippee relationship must be before a jury can infer a gift-

based personal benefit. Instead, we simply hold that the record's

evidence of O'Neill and Bray’s friendship, coupled with O'Neill's

testimony that the tip might lead to certain future benefits,

provided a sufficient basis for a reasonable jury to conclude that

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O'Neill acted in expectation of a personal benefit. See Parigian,

824 F.3d at 16 n.8 (stating that "anticipation of a personal

benefit in return for a breach of duty surely suffices").

2. Bray's Knowledge of O'Neill's Anticipation of a
Benefit and Fiduciary Breach

Liability for securities fraud also requires proof that

the defendant acted with scienter, defined as "a mental state

embracing intent to deceive, manipulate, or defraud." Ernst &

Ernst v. Hochfelder, 425 U.S. 185, 193 n.12 (1976). With respect

to criminal violations of § 10(b) and Rule 10b-5, this means that

the government must “prove that the defendant 'willfully' violated

the provision . . . that is, that the defendant acted with

'culpable intent.'" Parigian, 824 F.3d at 11 (quoting 15 U.S.C.

§ 78ff(a), and O'Hagan, 521 U.S. at 666); see also United States

v. Cassese, 428 F.3d 92, 98 (2d Cir. 2005) (defining willfulness

"as a realization on the defendant's part that he was doing a

wrongful act under the securities laws" and that such act "involved

a significant risk of effecting the violation that . . . occurred"

(internal quotation marks and citations omitted)).

With these principles in mind, we find sufficient

evidence in the record to support a finding that Bray knew O'Neill

tipped him in expectation of a personal benefit.6 Again, O'Neill

6 We note that the Supreme Court expressly declined to address
what level or type of knowledge a criminal tippee must have
regarding a tipper's receipt of a personal benefit. Salman, 137

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and Bray's close relationship is our starting point: though Bray

may not have known the exact benefit O'Neill sought in exchange

for the tip, a reasonable jury could have readily inferred

O'Neill's intent to benefit Bray. See United States v. Salman,

792 F.3d 1087, 1092 (9th Cir. 2015) (observing, in the context of

a three-person tipping chain, that an ultimate tippee could

“readily have inferred” an insider’s intent to benefit the initial

tippee-turned-tipper based on his awareness of the insider and

tipper’s close relationship), aff'd, 137 S. Ct. 420 (2016).

Bray's actions after Eastern announced the Wainwright

acquisition bolster this conclusion. He thanked O'Neill for the

tip and, unprompted, offered him an opportunity to invest in the

Watertown Project on two separate occasions, the same project for

which he requested the tip in the first place. Before this, Bray

had never offered O'Neill a similar opportunity and had rarely (if

ever) made such offers to anyone else at Oakley. Consequently,

the jury was entitled to conclude that Bray knew O’Neill sought a

personal benefit in exchange for the tip.

S. Ct. at 425 n.1. For its part, the Second Circuit held that
Dirks requires that a tippee must "know[] that the insider
disclosed confidential information in exchange for a personal
benefit." Newman, 773 F.3d at 448, 449. In their briefs, both
Bray and the government seemingly assume that this standard
applies. Ultimately, the issue is of no consequence since we find
that a jury could reasonably conclude that Bray possessed the
requisite knowledge even under the Second Circuit's standard.

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 A reasonable jury could also infer that Bray knew O'Neill

had breached a duty of confidentiality by giving him the Wainwright

tip. Though O'Neill did not tell Bray that he was working on the

Wainwright acquisition, Bray knew what O'Neill did for a living

and, presumably, that O’Neill had evaluated potential acquisition

targets in the past. Similarly, up until that point, O'Neill had

only given Bray investing advice based on publicly-available

information in the course of casual conversation. However, this

time Bray expressly requested a "tip" on which he could make a

"big score." O'Neill then passed Bray the Wainwright tip in a

surreptitious manner, after which Bray neither made any comments

nor asked any questions.

The actions Bray took after receiving the tip are equally

compelling. The day after getting the Wainwright tip, Bray sold

thousands of shares in his trading account, generating hundreds of

thousands of dollars in proceeds, and then immediately used those

funds to buy tens of thousands of Wainwright shares. Though Bray

was no stranger to holding concentrated positions in his portfolio

-- at one point in 2009, 40% of his overall account holdings were

in Citigroup -- he had never previously held such a position in a

stock as illiquid as Wainwright.7 Unlike all his previous ignoring

7
The record shows that Citigroup shares, for example,
routinely had daily trading volumes in the tens of millions. These
numbers differed drastically from those for Wainwright shares,
which typically topped out in the low thousands.

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of O’Neill’s prior stock recommendations, in this instance Bray

bought as many Wainwright shares as possible over the next month,

a move even he admitted to his E*Trade broker seemed "kind of

ridiculous." Later, when O'Neill went to Bray with news of the

FINRA inquiry, Bray did not act surprised when he "learned" that

the tip stemmed from nonpublic information or think to ask why

O'Neill had given him a tip in breach his duty of confidentiality.

Instead, Bray's first instinct was to assure O'Neill that he had

not told anyone about the tip and to develop a cover story.

Simply put, all of the evidence regarding the tip and

its aftermath show that there was a sufficient basis from which a

jury could reasonably conclude beyond a reasonable doubt that Bray

knew O'Neill had anticipated a benefit and breached a fiduciary

duty to his employer.

B. Jury Instruction Claims

We now turn to Bray’s challenges concerning the district

court's jury instructions. Bray claims he is at least entitled to

a new trial because the district court wrongly instructed the jury

on the mens rea element of his offense. Specifically, Bray argues

that the district court erroneously told the jury that it could

convict him of securities fraud so long as it found that he “knew

or . . . should have known” that O’Neill had breached a duty of

confidentiality by giving him the Wainwright tip. Bray similarly

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insists that the district court’s instructions also erred by

equating the concept of “willful blindness” with negligence.

Since Bray did not object to these instructions at trial,

we review for plain error.8 See Fed. R. Crim. P. 30(d); United

States v. Paniagua-Ramos, 251 F.3d 242, 246 (1st Cir. 2001). In

order to establish plain error, Bray must show "(1) that an error

occurred; (2) that the error was clear or obvious; (3) that the

error affected his substantial rights; and (4) that the error also

seriously impaired the fairness, integrity, or public reputation

of judicial proceedings." United States v. Riccio, 529 F.3d 40,

46 (1st Cir. 2008), modified on reconsideration, 567 F.3d 39 (1st

Cir. 2009). The standard is "exceedingly difficult to satisfy in

jury instruction cases." United States v. González-Vélez, 466

F.3d 27, 35 (1st Cir. 2006). “[H]ence, reversal constitutes a

remedy that is granted sparingly.” United States v. Gelin, 712

F.3d 612, 620 (1st Cir. 2013).

8 The Government argues that Bray waived his challenge to the
"knew or under all the circumstances . . . should have known"
instruction because he affirmatively requested that the district
court use that language and referenced the instruction during his
opening statement and closing arguments. However, Bray's proposed
instruction concerned O'Neill's knowledge of the Wainwright
information's confidential status, not Bray's personal knowledge
of O'Neill's fiduciary breach. Meanwhile, Bray's opening
statement and closing arguments came after the district court had
endorsed this language. In our view, these actions do not evidence
an "intentional relinquishment or abandonment of a known right."
United States v. Olano, 507 U.S. 725, 733 (1993) (quoting Johnson
v. Zerbst, 304 U.S. 458, 464 (1938)).

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 Nonetheless, our recent decisions show that the district

court clearly erred by including the “should have known” language

in its jury instructions. McPhail, 831 F.3d at 9 (indicating that

the standard, as applied to a tipper’s knowledge regarding whether

a duty of trust and confidence arose between him and his source of

information, “was likely error”); Parigian, 824 F.3d at 11 (stating

that “the ‘knew or should have known’ formulation runs up against

a decades-long presumption that the government must prove that the

defendant knew the facts that made his conduct illegal” (citing

Elonis v. United States, 135 S. Ct. 2001, 2009-10 (2015), Staples

v. United States, 511 U.S. 600, 605-06 (1994), and United States

v. Ford, 821 F.3d 63, 67-72 (1st Cir. 2016))). Though Bray’s trial

predated these decisions, "[t]he plainness of an error is

considered at the time of an appeal." United States v. Morales,

801 F.3d 1, 10 (1st Cir. 2016) (citing Henderson v. United States,

133 S. Ct. 1121, 1124-25 (2013), and United States v. Farrell, 672

F.3d 27, 36 (1st Cir. 2012)). Moreover, though neither of these

cases actually held that a district court's use of the "should

have known" standard constituted clear error, "[t]he absence of a

decision directly on point does not remove the potential for a

finding of plain error." Id. Rather, "the inquiry is always

whether the error is open to doubt or question." Id. In this

sense, McPhail and Parigian make the error "plain," especially in

light of recent guidance from the Supreme Court. See Salman, 137

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S. Ct. at 423 (stating that a "tippee acquires the tipper's duty

to disclose or abstain from trading if the tippee knows the

information [given to him by the tipper] was disclosed in breach

of the tipper's duty" of confidentiality (emphasis added)).

Accordingly, Bray's challenge to the "should have known" language

in the district court's jury instructions survives the first two

prongs of the plain error test.

The principles expressed in these and other cases

likewise indicate that the district court clearly erred in defining

the “willful blindness” standard. See Global-Tech Appliances,

Inc. v. SEB S.A., 563 U.S. 754, 769-70 (2011) (noting that willful

blindness has “an appropriately limited scope that surpasses

recklessness and negligence” and expressly contrasting willful

blindness with “a negligent defendant . . . who should have known

of a similar risk but, in fact, did not”). A willful blindness

instruction is meant to "inform[] jurors that they may ‘impose

criminal liability on people who, recognizing the likelihood of

wrongdoing, nonetheless consciously refuse to take basic

investigatory steps.’” United States v. Griffin, 524 F.3d 71, 77

n.4 (1st Cir. 2008) (quoting United States v. St. Michael’s Credit

Union, 880 F.2d 579, 585 (1st Cir. 1989)). The instruction in

this case, however, mistakenly suggested that the jury could find

Bray had willfully ignored O'Neill's fiduciary breach even if Bray

had not "consciously and deliberately avoided learning" about the

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violation. See United States v. Pérez-Meléndez, 599 F.3d 31, 41

(1st Cir. 2010).

Regardless, even if we assume, without deciding, that

these errors affected Bray’s substantial rights,9 our resolution

of Bray’s sufficiency of the evidence claims shows that he cannot

satisfy the fourth prong of plain error review. See United States

v. Kinsella, 622 F.3d 75, 83 (1st Cir. 2010) (holding that we may

affirm a conviction notwithstanding an obvious or prejudicial

error if “the error does not distort the fairness or integrity of

lower court proceedings in some extreme way”). That is, the

government presented ample evidence that Bray knew O’Neill had

breached a duty of confidentiality by tipping, or at least

possessed the requisite “culpable intent.” Parigian, 824 F.3d at

11.

Bray relies on our decision in United States v. Delgado-

Marrero, where we held that an instructional error met the fourth

9Our assumption regarding the third prong of the plain error
test may prove dubious. “[I]n most cases,” this prong of the plain
error test requires that “the error . . . have been prejudicial:
It must have affected the outcome of the district court
proceedings.” United States v. Olano, 507 U.S. 725, 734 (1993).
Viewing the challenged instructions against the backdrop of the
jury charge as a whole, United States v. Pennue, 770 F.3d 985, 990
(1st Cir. 2014), and considering the strength of the government’s
evidence on the knowledge issue, it seems “quite likely” that a
jury would have convicted Bray even had it been instructed as he
now suggests, United States v. O’Brien, 435 F.3d 36, 40 (1st Cir.
2006). Regardless, both of these factors weigh heavily on our
analysis under the fourth prong of the plain error test as well.

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prong of the plain error test because the evidence offered against

the defendant on the contested element was not “overwhelming and

uncontroverted.” 744 F.3d 167, 189 (1st Cir. 2014) (citing United

States v. Cotton, 535 U.S. 625, 631-33 (2002)). He claims that

even if the government’s evidence as to his knowledge of O’Neill’s

fiduciary breach were legally sufficient, the question was close

enough such that a properly instructed jury could have acquitted

him, thereby implicating Delgado-Marrero and the fourth plain

error prong. However, Bray’s argument again downplays the strength

of the government’s evidence against him. Bray’s furtive behavior

in the pub room, coupled with the fact that he engaged in trading

behavior that even he admitted would seem “ridiculous” to someone

possessing only publicly-available information, provided a solid

base on which a jury could find him guilty.

In any event, the district court emphasized to the jury

that the government had to prove “Bray acted willfully, knowingly,

and with the intent to defraud.” The district court did not render

Bray’s state of mind “an inconsequential afterthought,” Delgado-

Marrero, 744 F.3d at 187, and therefore any instructional error

was “simply not of such magnitude or consequence that it would

undermine faith in the judicial system were it to stand

uncorrected,” United States v. Padilla, 415 F.3d 211, 221 (1st

Cir. 2005).

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 In sum, different jury instructions “would have been of

little help” to Bray. See United States v. Cormier, 468 F.3d 63,

72 (1st Cir. 2006). Therefore, Bray has “fallen short of the

‘rather steep’ road to success under the ‘exacting’ plain-error

standard.” See Delgado-Marrero, 744 F.3d at 203 (quoting Gelin,

712 F.3d at 620, and Long v. Fairbank Reconstruction Corp., 701

F.3d 1, 5 (1st Cir. 2012)).

III. Conclusion

For the foregoing reasons, we affirm Bray’s conviction.

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