Lawyering the Presidency

• Author: Deborah Pearlstein
• Position: Professor of Law, Benjamin N. Cardozo School of Law, Yeshiva University
• Pages: 899-952

Lawyering the Presidency

DEBORAH PEARLSTEIN*

Among its many profound effects on American life, the Trump presi-

dency triggered a surge of interest in reforms that might better check the

exercise of presidential power—from enhancing ethics and transparency

requirements to reining in sweeping congressional delegations of sub-

stantive authority. Yet these reform efforts arise against a wholly unset-

tled debate about the function and effectiveness of existing checks,

perhaps none more so than the role of Executive Branch legal counsel.

With courts often deferential, and Congress often hamstrung by partisan

polarization, scholars have focused on the experiences of Executive

Branch lawyers to illuminate whether counsel functions as part of an

“internal separation of powers,” an effective first-order constraint on the

presidency. Yet while these descriptive accounts are invaluable, they are

also limited to the attorney side of an attorney–client relationship, leav-

ing much unanswered about whether and why presidential advisors might

heed their advice. And while the search for signs of “constraint” is

essential, this conceptual framing has tended to obscure other ways in

which counsel may influence decisionmaking, dynamics that might prove

essential for reformers to address if they are to achieve the change they

seek. Aiming to help fill these gaps, this Article draws on an original sur-

vey of more than three dozen former senior U.S. national security policy

officials, from the Cabinet Secretary level at the most senior to National

Security Council staff at the most junior, to examine when and why poli-

cymaking clients engage counsel’s advice surrounding the use of force,

and how that advice may shape or reshape policymakers’ existing nor-

mative preferences. Among its findings, the depth and bipartisan breadth

of officials’ sense of obligation to engage counsel suggests that the exist-

ing literature may be underestimating counsel’s capacity to influence. At

the same time, as this Article describes, counsel is structurally capable of

exerting that influence in multidirectional ways. When policymakers’

own normative instincts lead them to want to avoid external limits on ex-

ecutive power, counsel’s insistence that such limits be observed can at

times “constrain” executive action. But where, as may also arise,

* Professor of Law, Benjamin N. Cardozo School of Law, Yeshiva University. © 2022, Deborah

Pearlstein. Earlier versions of this study were presented at faculty workshops at Georgetown University

Law Center and Stanford University, as well as Arizona, Cardozo, Drake, and Emory Law Schools.

Many thanks to all participants, as well as to John Bellinger, Christopher Chyba, Mary DeRosa, Brian

Egan, Christopher Fonzone, Rosemary Hart, Rebecca Ingber, Marty Lederman, Robert Litt, David

Luban, Michael Pollack, Milton Regan, Daphna Renan, Shalev Roisman, Scott Sagan, and Kate Shaw.

Great thanks for exceptional research assistance to Amanda Sewanan and Mariya Dekhtyar. Above all,

sincere thanks to the remarkable men and women who took the time to reflect on their experience of

service. The study would not have been possible without them.

899

policymakers would prefer more external checks on presidential behav-

ior, counsel’s permission not to abide by those checks may have an unin-

tentionally encouraging effect. Indeed, when policymakers seek a

politically palatable justification for avoiding action, the unavailability

of a narrow construction of presidential authority may deprive officials

of an effectively action-limiting out. As this Article concludes, if the post-

Trump goal is to improve counsel’s function as a “constraint” on power,

reforms beyond simply increasing transparency or quality will be

required.

TABLE OF CONTENTS

INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 901

I. QUESTIONING COUNSEL’S INFLUENCE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 907

A. METHODS . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 909

1. Topic of Study . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 909

2. Target Population. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 910

3. Survey Questions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 911

4. Sample Recruiting . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 913

B. TESTING THE NONINFLUENCE HYPOTHESIS . . . . . . . . . . . . . . . . . . . . . 914

II. DECONSTRUCTING COUNSEL’S INFLUENCE . . . .. . . . . . . . . . . . . . . . . . . . . . 920

A. BUREAUCRATIC INTEGRATION AND RELATIONAL LAWYERING .. . . . . 921

B. VARIED PURPOSE, COMMON EFFECT . . . . . . . . . . . . . . . . . . . . . . . . . . 924

C. LEGAL FLUENCY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 926

III. CHARTING DECISIONAL DYNAMICS: INTERNAL SEPARATION OF

POWERS AS THREE -WAY RATCHET . .. . . . . . . . . . . . . . . . . . . . . . . . . . . 929

A. INFLUENCE OVER TIME . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 930

B. PERMISSIVE INFLUENCE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 936

C. JUSTIFICATION INFLUENCE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 942

IV. IMPLICATIONS FOR REFORM . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 944

A. MODELING EDUCATIONAL LAWYERING . . . . . . . . . . . . . . . . . . . . . . . 946

B. IMPROVING LEGAL FLUENCY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 949

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C. PROTECTING LEGAL INFLUENCE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 950

CONCLUSION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 951

INTRODUCTION

Among its many profound effects on American life, the Trump presidency trig-

gered a surge of interest among scholars and policymakers in structural reforms

to better check the exercise of presidential power.

1

See, e.g., BOB BAUER & JACK GOLDSMITH, AFTER TRUMP: RECONSTRUCTING THE PRESIDENCY

(Amy Marks ed., 2020); Emily Berman, Weaponizing the Office of Legal Counsel, 62 B.C. L. REV. 515,

516–17 (2021); Oona A. Hathaway, National Security Lawyering in the Post-War Era: Can Law

Constrain Power?, 68 UCLA L. REV. 2, 7–8 (2021); Article I: Constitutional Perspectives on the

Responsibility and Authority of the Legislative Branch: Hearing Before the H. Comm. on Rules, 116th

Cong. 2 (2020); see also Annie L. Owens, Reforming the Office of Legal Counsel: Living Up to Its Best

Practices, AM. CONST. SOC’Y (Oct. 2020), https://www.acslaw.org/wp-content/uploads/2020/12/

Owens-Reforming-OLC-Final.pdf [https://perma.cc/X3K5-UT44] (describing recent efforts to reform

the Office of Legal Counsel).

The impulse is welcome, for

Trump’s presidency helped expose the fragility of many of the legal rules and

structures thought essential to guarding against an authoritarian executive—from

anticorruption measures to limits on the use of U.S. military force. Yet these

reform efforts arise against a wholly unsettled debate about the function and

effectiveness of existing checks, perhaps none more so than the role of Executive

Branch legal counsel. With the courts often slow to act or deferential to executive

judgment, and congressional oversight hobbled by partisan polarization, promi-

nent scholars in the pre-Trump era had come to champion the ability of Executive

Branch offices, such as the Justice Department Office of Legal Counsel (OLC), to

help forestall presidential illegality.

2

Bolstered by independent norms of profes-

sional ethics and practice, many argued counsel could be an effective internal

force for promoting executive compliance with law.

But even before Trump arrived in the White House, other scholars had begun

documenting the relative weakening of OLC’s role and a corresponding increase

in the influence of a more diffuse set of interagency lawyers—highlighting the

ways in which competing centers of legal advice could undermine their effective-

ness by encouraging forum shopping by policymakers seeking more permissive

guidance.

3

Today, former White House and Justice Department lawyers within

1.

2. See, e.g., Trevor W. Morrison, Stare Decisis in the Office of Legal Counsel, 110 COLUM. L. REV.

1448 (2010) (studying the OLC); cf. JACK GOLDSMITH, POWER AND CONSTRAINT: THE ACCOUNTABLE

PRESIDENCY AFTER 9/11 (2012) (discussing the role of military lawyers); Laura A. Dickinson, Military

Lawyers on the Battlefield: An Empirical Account of International Law Compliance, 104 AM. J. INT’L L.

1, 14–15 (2010) (studying the role of military lawyers and advisors); Michael P. Scharf, International

Law in Crisis: A Qualitative Empirical Contribution to the Compliance Debate, 31 CARDOZO L. REV.

45, 67–68 (2009) (studying the role of State Department Legal Advisers).

3. See Daphna Renan, The Law Presidents Make, 103 VA. L. REV. 805, 809–10 (2017); see also Elad

D. Gil, Totemic Functionalism in Foreign Affairs Law, 10 HARV. NAT’L SEC. J. 316, 337–38 (2019)

(explaining that a diffusion of power between legal offices causes “advice shopping”); BRUCE

ACKERMAN, THE DECLINE AND FALL OF THE AMERICAN REPUBLIC 68 (2010) (“[OLC] almost always

conclude[s] that the president can do what he wants.”); Cornelia T.L. Pillard, The Unfulfilled Promise of

the Constitution in Executive Hands, 103 MICH. L. REV. 676, 717 (2005) (“[T]he more critically OLC

2022] LAWYERING THE PRESIDENCY 901