STRINE, Chief Justice:
I. INTRODUCTION
Determining whether a plaintiff has pled facts supporting an inference that a director cannot act independently of an interested director for purposes of demand excusal under Aronson
can be difficult. And this case illustrates that. But in that determination, it is important that the trial court consider all the particularized facts pled by the plaintiffs about the relationships between the director and the interr ested party in their totality and not in isolation from each other, and draw all reasonable inferences from the totality of those facts in favor of the plaintiffs. In this case, the plaintiffs pled not only that the director had a close friendship of over half a century with the interested party, but that consistent with that deep friendship, the director’s primary employment (and that of his brother) was as an executive of a company over which the interested party had substantial influence. These, and other facts of a similar nature, when taken together, support an inference that the director could not act independently of the interested party. . Because of that, the plaintiffs pled facts supporting an inference that a majority of the board who approved the interested transaction they challenged could not consider a demand impartially. Therefore, we reverse and remand so that the plaintiffs can prosecute this derivative action.
II. BACKGROUND
This case involves an appeal from a complicated transaction between a private company whose equity is wholly owned by the family of A.R. Sanchez, Jr., Sanchez Resources, LLC (hereinafter, the “Private Sanchez Company”), and a public company in which the Sanchez family constitutes-the largest stockholder bloc with some 16% of the shares and that' is dependent on the Private Sanchez Company for all --of its management services, Sanchez Energy Corporation (the “Sanchez Public Company”). The transaction at issue required the Sanchez Public Company to pay $78 million to: i) help the Private Sanchez Company buy out the interests of a private equity investor; ii) acquire an interest in certain properties with energy-producing potential from the Private Sanchez Company; iii) facilitate the joint production of 80,000 acres of property between the Sanchez Private and Public Companies; and iv) fund a cash payment of $3.4.4 million to the Private Sanchez Company. In this derivative action, the plaintiffs allege that this transaction involved a gross overpayment by the Sanchez Public- -Company; which unfairly benefited the Private Sanchez-Company by allowing it to use the Sanchez Public Company’s funds to buy out their private equity partner, obtain a large cash payment for itself, and obtain- a contractual right to a lucrative royalty stream that was unduly favorable to the Private Sanchez Company and thus unfairly onerous to the Sanchez Public Company. As to the latter, the plaintiffs allege that the royalty payment was not only, unfair, but was undisclosed to the Sanchez Public Company .stockholders, and that it was the Sanchez family’s desire to conceal the royalty obligation that led to what can be fairly described as a convoluted transaction structure. .
The Court of .Chancery dismissed the complaint, finding that the defendants were correct in their contention that the plaintiffs had not pled demand excusal under Ar
onson
In a thorough and careful opinion, the Court of Chancery examined both prongs of
Aronson
and concluded
that the plaintiffs had not satisfied their pleading burden to show that demand was excused under either.
On appeal, the plaintiffs argue that the Court of Chancery was wrong on both scores.
But, in resolving this appeal, we focus on only one issue, which is outcome-determinative. The parties agree that two of the five directors on the Sanchez Public Company board were not disinterested in the transaction: A.R. Sanchez, Jr., the Public Company’s Chairman; and his son, Antonio R. Sanchez, III, the Sanchez Public Company’s President and CEO. For the sake of clarity, we refer to the patriarch of the Sanchez family, A.R. Sanchez, Jr., as Chairman Sanchez.
The question for
Aronson
purposes was therefore whether the plaintiffs had pled particularized facts raising a pleading-stage doubt about the independence of one of the other Sanchez Public Company directors. If they had, the defendants and the Court of Chancery itself recognized that the plaintiffs would have pled grounds for demand excusal under
Aronson.
III. ANALYSIS
To plead demand excusal under Rule 23.1, a plaintiff in a derivative action must plead particularized facts creating a “reasonable doubt” that either “(1) the directors are disinterested and independent or (2) the challenged transaction was otherwise the product of a valid exercise of business
judgment.”
Although there is a heightened burden under Rule 23.1 to plead particularized facts, when a motion to dismiss for failure to make a demand is made, all reasonable inferences from the pled facts must nonetheless be drawn in favor of the plaintiff in determining whether the plaintiff has met its burden under Aronson.
The closest question below centered on director Alan Jackson. The complaint bases its challenge to Jackson’s independence on two related grounds. First, it pleads that “[Chairman] Sanchez and Jackson have been close friends for more than five decades.”
Consistent with this allegation, the complaint indicates that when Chairman Sanchez ran for Governor of Texas in 2012, Jackson donated $12,500 to his campaign.
Second, the complaint pleads facts supporting an inference that Jackson’s personal wealth is largely attributable to business interests over which Chairman Sanchez has substantial influence. According to the complaint, Jackson’s full-time job and primary source of income is as an executive at IBC Insurance Agency, Ltd.
IBC Insurance provides insurance brokerage services to the Sanchez Public Company and other Sanchez affiliates.
But even more importantly, IBC Insurance is a wholly owned subsidiary of International Bancshares Corporation (“IBC”), a company of which Chairman Sanchez is the largest stockholder
and a director who IBC’s board has determined is not independent under the NASDAQ Marketplace Rules.
Not only does Jackson work full-time for IBC Insurance, so too does his brother.
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STRINE, Chief Justice:
I. INTRODUCTION
Determining whether a plaintiff has pled facts supporting an inference that a director cannot act independently of an interested director for purposes of demand excusal under Aronson
can be difficult. And this case illustrates that. But in that determination, it is important that the trial court consider all the particularized facts pled by the plaintiffs about the relationships between the director and the interr ested party in their totality and not in isolation from each other, and draw all reasonable inferences from the totality of those facts in favor of the plaintiffs. In this case, the plaintiffs pled not only that the director had a close friendship of over half a century with the interested party, but that consistent with that deep friendship, the director’s primary employment (and that of his brother) was as an executive of a company over which the interested party had substantial influence. These, and other facts of a similar nature, when taken together, support an inference that the director could not act independently of the interested party. . Because of that, the plaintiffs pled facts supporting an inference that a majority of the board who approved the interested transaction they challenged could not consider a demand impartially. Therefore, we reverse and remand so that the plaintiffs can prosecute this derivative action.
II. BACKGROUND
This case involves an appeal from a complicated transaction between a private company whose equity is wholly owned by the family of A.R. Sanchez, Jr., Sanchez Resources, LLC (hereinafter, the “Private Sanchez Company”), and a public company in which the Sanchez family constitutes-the largest stockholder bloc with some 16% of the shares and that' is dependent on the Private Sanchez Company for all --of its management services, Sanchez Energy Corporation (the “Sanchez Public Company”). The transaction at issue required the Sanchez Public Company to pay $78 million to: i) help the Private Sanchez Company buy out the interests of a private equity investor; ii) acquire an interest in certain properties with energy-producing potential from the Private Sanchez Company; iii) facilitate the joint production of 80,000 acres of property between the Sanchez Private and Public Companies; and iv) fund a cash payment of $3.4.4 million to the Private Sanchez Company. In this derivative action, the plaintiffs allege that this transaction involved a gross overpayment by the Sanchez Public- -Company; which unfairly benefited the Private Sanchez-Company by allowing it to use the Sanchez Public Company’s funds to buy out their private equity partner, obtain a large cash payment for itself, and obtain- a contractual right to a lucrative royalty stream that was unduly favorable to the Private Sanchez Company and thus unfairly onerous to the Sanchez Public Company. As to the latter, the plaintiffs allege that the royalty payment was not only, unfair, but was undisclosed to the Sanchez Public Company .stockholders, and that it was the Sanchez family’s desire to conceal the royalty obligation that led to what can be fairly described as a convoluted transaction structure. .
The Court of .Chancery dismissed the complaint, finding that the defendants were correct in their contention that the plaintiffs had not pled demand excusal under Ar
onson
In a thorough and careful opinion, the Court of Chancery examined both prongs of
Aronson
and concluded
that the plaintiffs had not satisfied their pleading burden to show that demand was excused under either.
On appeal, the plaintiffs argue that the Court of Chancery was wrong on both scores.
But, in resolving this appeal, we focus on only one issue, which is outcome-determinative. The parties agree that two of the five directors on the Sanchez Public Company board were not disinterested in the transaction: A.R. Sanchez, Jr., the Public Company’s Chairman; and his son, Antonio R. Sanchez, III, the Sanchez Public Company’s President and CEO. For the sake of clarity, we refer to the patriarch of the Sanchez family, A.R. Sanchez, Jr., as Chairman Sanchez.
The question for
Aronson
purposes was therefore whether the plaintiffs had pled particularized facts raising a pleading-stage doubt about the independence of one of the other Sanchez Public Company directors. If they had, the defendants and the Court of Chancery itself recognized that the plaintiffs would have pled grounds for demand excusal under
Aronson.
III. ANALYSIS
To plead demand excusal under Rule 23.1, a plaintiff in a derivative action must plead particularized facts creating a “reasonable doubt” that either “(1) the directors are disinterested and independent or (2) the challenged transaction was otherwise the product of a valid exercise of business
judgment.”
Although there is a heightened burden under Rule 23.1 to plead particularized facts, when a motion to dismiss for failure to make a demand is made, all reasonable inferences from the pled facts must nonetheless be drawn in favor of the plaintiff in determining whether the plaintiff has met its burden under Aronson.
The closest question below centered on director Alan Jackson. The complaint bases its challenge to Jackson’s independence on two related grounds. First, it pleads that “[Chairman] Sanchez and Jackson have been close friends for more than five decades.”
Consistent with this allegation, the complaint indicates that when Chairman Sanchez ran for Governor of Texas in 2012, Jackson donated $12,500 to his campaign.
Second, the complaint pleads facts supporting an inference that Jackson’s personal wealth is largely attributable to business interests over which Chairman Sanchez has substantial influence. According to the complaint, Jackson’s full-time job and primary source of income is as an executive at IBC Insurance Agency, Ltd.
IBC Insurance provides insurance brokerage services to the Sanchez Public Company and other Sanchez affiliates.
But even more importantly, IBC Insurance is a wholly owned subsidiary of International Bancshares Corporation (“IBC”), a company of which Chairman Sanchez is the largest stockholder
and a director who IBC’s board has determined is not independent under the NASDAQ Marketplace Rules.
Not only does Jackson work full-time for IBC Insurance, so too does his brother.
Both of them service the work that IBC Insurance does for the Sanchez Public and Private Companies.
The complaint also alleges that the approximately $165,000 Jackson earned as a Sanchez Public Company director constituted “30-40% of Jackson’s total income for 2012.”
The plaintiffs contend that these pled facts support an inference that Jackson cannot act independently of Chairman Sanchez, because he is Sanchez’s close friend of a half century, derives his primary employment from a company over which Sanchez has substantial control, has a brother in the same position, and that the coincidence of these personal and business ties are, well, no coincidence. In its opinion, the Court of Chancery disagreed with the plaintiffs. After examining all of these factors, the Court of Chancery concluded that the plaintiffs had not pled facts overcoming the presumption that Jackson was independent.
The defendants defend the Court of Chancery’s reasoning on appeal, and stress that it relied on precedent such as
Beam v. Stewart,
and reflected a careful assessment of the pled facts and whether they were sufficient to compromise Jackson’s independence under
Aronson.
They also note, as did the Court of Chancery,
that this Court has admonished derivative plaintiffs to use the books and record process to aid them in satisfying Aronson’s stringent pleading test and that, if the plaintiffs came up short, it was their own fault for not using this avenue.
We agree with the defendants that the Court of Chancery diligently grappled with this close question and justified its decision that the plaintiffs had not pled facts supporting an inference that Jackson could not act independently of Sanchez in terms of relevant precedent. But, employing the
de novo
review that governs this appeal,
we do not come to the same conclusion as the Court of Chancery. The reason for that is that the Court of Chancery’s analysis seemed to consider the facts the plaintiffs pled about Jackson’s personal friendship with Sanchez and the facts they pled regarding his business relationships as entirely separate issues. Having parsed them as categorically distinct, the Court of Chancery appears to have then concluded that neither category of facts on its own was enough to compromise Jackson’s independence for purposes of demand excu-sal.
The problem with that approach is that our law requires that all the pled facts regarding a director’s relationship to the interested party be considered in full context in making the, admittedly imprecise, pleading stage determination of independence.
In that consideration, it cannot be ignored that although the plaintiff is bound to plead particularized facts in pleading a derivative complaint, so too is the court bound to draw all inferences from those particularized facts in favor of the plaintiff, not the defendant, when dismissal of a derivative complaint is sought.
Here, the plaintiffs did not plead the kind of thin - social-circle friendship, for want- of a better way to put it, which was at issue in
Beam. In
that case, we held that allegations that directors “moved in the same social circles, attended the same weddings, developed business relationships before joining the board, and described each other as ‘friends,’ ... are insufficient, without more, to rebut the presumption of independence.”
In saying that, we did not suggest that deeper human friendships could not exist that would have the effect of compromising a director’s independence. When, as here, a plaintiff has pled that a director has been close friends with an interested party for a half century, the plaintiff has pled facts quite different from those at issue in Beam,
Close friendships of that duration are likely considered- precious by many people, and are rare. People drift apart for many reasons, and when a close relationship endures for that long, a pleading stage inference arises that it is important to the parties.
The plaintiffs did not rely simply on that proposition, however. They pled facts regarding the economic relations of Jackson and Chairman Sanchez that buttress their contention that they are confidantes and that there is a reasonable doubt that Jackson can act impartially in a matter of economic importance to Sanchez personally. It may be that it is entirely coincidental that Jackson’s full-time job is as an executive at a Subsidiary of a corporation over which Chairman Sanchez has substantial influence, as the largest stockholder, director, and the Chairman of an important source of brokerage work. It may be that it is also coincidental that Jack
son’s brother also works there. It may be coincidental that Jackson and his brother both work on insurance brokerage work for the Sanchez Public and Private Companies there. And it may be coincidental that Jackson finds himself a director of the Sanchez Public Company. But rather certainly, there arises a pleading stage inference that Jackson’s economic positions derive in large measure from his 50-year close friendship with Chairman Sanchez, and that he is in these positions because Sanchez trusts, cares for,' and respects him.
If that is true, there is of course nothing wrong with that. Human relationships of that kind are valuable. In this context, however, where the question is whether the plaintiffs have met' their pleading burden to plead facts suggesting that Jackson cannot act' independently of Chairman Sanchez, these obvious inferences that arise from the pled facts require that the defendants’ motion to dismiss' be denied.
In other words, using
the precise parlance of
Aronson,
the plaintiffs pled particularized facts, that when considered in the plaintiff-friendly manner required, create a reasonable doubt about Jackson’s independence.
As to this point, we also think it useful to note that although, like the Court of Chancery, we agree that it would have been ideal for the plaintiffs to use the books and records tool,
as our prior cases have encouraged, that instrument may have been of limited utility on this particular point. It may be that the Sanchez Public Company has a file of the disclosure questionnaires for the board that would provide more detail about the thickness of the relationship between Chairman Sanchez and Jackson.
But we cannot hold the plaintiffs’ failure to undertake additional investigation against them when, as here, the facts pled in the complaint support an inference that a majority of the board lacked independence.
'Because we conclude that the plaintiffs pled demand excusal under the first prong of
Aronson,
we need not and therefore do not reach the other issues presented on appeal. Therefore, the judgment of the Court of Chancery of November 25, 2014 dismissing this case is reversed, and this case is remanded for further proceedings consistent with this opinion.