Indigenous Environmental Network et al v. Trump et al

Filing 147

ORDER: IT IS ORDERED that Plaintiffs' 82 Renewed Motion for Preliminary Injunction and Application for Temporary Restraining Order is DENIED; Plaintiffs' 136 Renewed Request for a Preliminary Injunction and Application for Temporary Res training Order is DENIED; Plaintiffs' 108 Motion for Leave to File a Second Amended Complaint is DENIED; Plaintiff's 142 Motion for Leave to File a Third Amended Complaint is DENIED. The Parties shall file simultaneous briefing, not to exceed 10,000 words, on the issues listed in Part III.b of this Order within 30 days of the issuance of this Order. SEE ORDER FOR FULL DETAILS. Signed by Judge Brian Morris on 10/16/2020. (SLR)

IN THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MONTANA
GREAT FALLS DIVISION
INDIGENOUS ENVIRONMENTAL
NETWORK and NORTH COAST RIVERS
ALLIANCE,
Plaintiffs,

4:19-cv-00028-BMM

ORDER

vs.
PRESIDENT DONALD J. TRUMP, et al.,
Defendants,
and
TRANSCANADA KEYSTONE
PIPELINE, LP, a Delaware limited
partnership, and TC ENERGY
CORPORATION, a Canadian Public
Company,
Defendant-Intervenors.

INTRODUCTION
Indigenous Environmental Network (“IEN”) and North Coast Rivers
Alliance (“NCRA”) (collectively, “Plaintiffs”) brought this action against President
Donald J. Trump and various government agencies and agents in their official
capacities (“Federal Defendants”). Plaintiffs allege that President Trump violated

the Property Clause of the U.S. Constitution, the Commerce Clause of the U.S.
Constitution, and Executive Order 13,337 when he issued a Presidential Permit in
2019 (“2019 Permit”) to Defendant-Intervenors TransCanada Keystone Pipeline,
LP and TC Energy Corporation (collectively, “TC Energy”) to construct a crossborder segment of the oil pipeline known as Keystone XL (“Keystone”).
BACKGROUND
Plaintiffs filed this action on April 5, 2019, to challenge President Trump’s
issuance of the 2019 Permit to construct the cross-border segment of Keystone.
(Doc. 1). The Court described the factual history of this case in detail in a previous
Order denying Motions to Dismiss and a Motion for a Preliminary Injunction.
(Doc. 73 at 2–14). All Parties have filed motions since that Order. TC Energy filed
a Motion for Summary Judgment on January 24, 2020. (Doc. 77). Plaintiffs filed a
Renewed Motion for Preliminary Injunction and Application for Temporary
Restraining Order on January 31, 2020. (Doc. 82). Federal Defendants and
Plaintiffs both filed Motions for Summary Judgment on February 25, 2020. (Docs.
95, 100). Plaintiffs filed for Leave to File a Second Amended Complaint on March
3, 2020. (Doc. 108). Plaintiffs filed another Renewed Request for a Preliminary
Injunction and Application for Temporary Restraining Order on April 14, 2020.
(Doc. 136). And Plaintiffs filed a Motion for Leave to File a Third Amended
Complaint on August 21, 2020. (Doc. 142).
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This case presents novel and complex questions of constitutional law and
statutory interpretation. The Court therefore sought supplemental briefing on
certain issues. (Doc. 74). The Court held a motion hearing on April 16, 2020, to
hear arguments on the supplemental briefing as well as motions pending at that
time. This Order will resolve many of the pending motions before the Court and
narrow the scope of the litigation. Certain issues will remain pending additional
briefing.
ANALYSIS
I.

Scope of the 2019 Presidential Permit
The 2019 Permit grants TC Energy permission “to construct, connect,

operate, and maintain pipeline facilities at the international border of the United
States and Canada . . . for the import of oil from Canada to the United States.”
Authorizing TransCanada Keystone Pipeline, L.P., To Construct, Connect,
Operate, and Maintain Pipeline Facilities at the International Boundary Between
the United States and Canada, 84 Fed. Reg. 13,101, 13,101 (March 29, 2019). The
Parties do not dispute that the 2019 Permit purportedly authorizes TC Energy to
construct, connect, and maintain a 1.2-mile segment of pipeline that extends from
the United States-Canada border up to and including the first mainline shut-off
valve. (Doc. 37 at 25; Doc. 42 at 9; Doc. 43 at 9–10).

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Plaintiffs assert that the 2019 Permit further authorizes TC Energy to
construct and operate an additional 875 miles of pipeline in the United States.
(Doc. 37 at 25; Doc. 99 at 1–9). The Court sought additional briefing on “whether
the permit authorizes only the 1.2-mile border facility” or “whether the permit
authorizes the entire Keystone XL Pipeline project.” (Doc. 74 at 1). Plaintiffs
argued that the 2019 Permit purports to approve “the portion [of the pipeline] in
the United States” as a whole. (Doc. 80 at 13-14). Plaintiffs point to TC Energy’s
application as describing “the whole of the pipeline.” Id. at 14. Plaintiffs finally
contend that the 2019 Permit “effectively authorizes the entire pipeline” as the
remainder of the project would not be built “but for the 2019 Permit.” Id. at 15.
The Court disagrees with Plaintiffs’ interpretation.
The 2019 Permit by its plain language applies only to the 1.2 miles from the
United States-Canada border, up to and including, the first mainline shut-off valve.
The first paragraph of the 2019 Permit grants permission to “construct, connect,
operate, and maintain pipeline facilities at the international border of the United
States and Canada at Phillips County, Montana.” 84 Fed. Reg. at 13,101 (emphasis
added). The text of this initial permission, as well as the remainder of the permit,
relates to authorization of pipeline facilities at the border. The 2019 Permit goes on
to define “Border facilities” to include “those parts of the Facilities consisting of a
36-inch diameter pipeline extending from the international border between the
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United States and Canada . . . to and including the first mainline shut-off valve in
the United States located approximately 1.2 miles from the international border.”
Id. (emphasis added). Each permit condition explicitly limits the “Border facilities”
term only. See id. at 13,101–03.
The 2019 Permit defines a broader “Facilities” term as the “portion in the
United States of the international pipeline project associated with the permittee’s
application for a Presidential permit . . . and any land, structures, installations, or
equipment appurtenant thereto.” Id. at 13,101. This broader term certainly
encompasses the full Keystone project. The 2019 Permit uses the term “Facilities”
only once -- to direct that the construction “of the Facilities (not including the
route) shall be, in all material respects and as consistent with applicable law,” as
described in TC Energy’s 2012 Application and 2017 Application for a
Presidential Permit. Id. at 13,101–02 (emphasis added). This “Facilities” term
purports to require TC Energy to comply with applicable laws throughout the
Keystone project. It does not in itself authorize the full Keystone project.
The 2017 Application provides further evidence for this reading. TC Energy
wrote in that application that it “requests a Presidential Permit” for “the specific
border crossing facilities associated with the Proposed Keystone XL Project.” The
application describes “border crossing facilities” as the 1.2 mile segment that
“extend[s] downstream from the United States border, in Phillips County, Montana
5

up to and including the first pipeline isolation valve, located at Milepost 1.2.”
TransCanada Keystone Pipeline, L.P., Application for Presidential Permit for
Keystone XL Pipeline Project, at 6 (Jan. 26, 2017).
Recent history and practice further support the Court’s limited reading of the
2019 Permit. Past presidential permits for border-crossing pipelines applied to the
project from the border crossing, up to and including, the first shut-off valves.
Examples include the permits for the Cochin Pipeline (authorizing 14.5 miles) and
the Magellan Pipeline (authorizing 600 feet). See Presidential Permit for Kinder
Morgan Cochin Pipeline (Renville County, ND facilities), 78 Fed. Reg. 73,582
(Dec. 6, 2013); Presidential Permit for Magellan Pipeline Company, L.P., 80 Fed.
Reg. 45,697 (July 31, 2015).
Older examples prove less clear in their terms, but they similarly indicate a
focus on border facilities and do not exempt projects from applicable laws. See,
e.g., Authorizing the Murphy Oil Corp. to Connect, Operate and Maintain a
Pipeline at the International Boundary Line Between the United States and Canada,
31 Fed. Reg. 6,204 (Apr. 21, 1966) (conditioning the “effectiveness of this permit
to authorize connection of the U.S. facilities at the international boundary line with
the facilities located in Canada” to the company’s compliance with Canadian,
federal, state, and local law).

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The 2019 Permit, though limited in its scope, places important conditions on
Keystone. It requires all Facilities to be built “consistent with applicable law,” and
that TC Energy acquire “any right-of-way grants or easements, permits, and other
authorizations” necessary to build the Border facilities. 84 Fed. Reg. at 13,101–02.
The 2019 Permit grants no exemptions to laws governing public land use or that
may require environmental analysis before authorizing a pipeline project. Those
public land use laws still apply to the Keystone XL project when it requires federal
actions—including over federal lands in that first 1.2-mile segment.
TC Energy sought and received a right-of-way from the U.S. Bureau of
Land Management (“BLM”) for the 1.2-mile segment. See BLM, Record of
Decision: Keystone XL Pipeline Project Decision to Grant Right-of-Way and
Temporary Use Permit on Federally Administered Land, DOI-BLM-MT-C0202020-0022-OTHER_NEPA (Jan. 22, 2020). BLM’s decision to grant the right-ofway remains subject to other litigation in this Court. See Bold All. v. U.S. Dep’t of
the Interior, 4:20-cv-00059-BMM-JTJ (D. Mont.); Assiniboine & Sioux Tribes of
the Ford Peck Indian Rsrv. v. U.S. Dep’t of the Interior, 4:20-cv-00044-BMM-JTJ
(D. Mont.).
II.

Resolution of Select Pending Motions
The Court’s analysis regarding the scope and content of the 2019 Permit

resolves, in turn, several pending motions before the Court.
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Motions for Temporary Restraining Order and Preliminary
Injunction
Plaintiffs filed three motions seeking a preliminary injunction and temporary
restraining order. (Docs. 27, 82, 136). The Court denied the first motion without
prejudice. (Doc. 73). The second and third motions remain pending. A court may
grant a preliminary injunction or temporary restraining order to preserve the status
quo pending final determination of an action. See Textile Unlimited, Inc. v.
A..BMH & Co., 240 F.3d 781, 786 (9th Cir. 2001). The issuance of a preliminary
injunction or temporary restraining order represent extraordinary remedies, that
should not be awarded as a matter of right, but only “upon a clear showing that the
plaintiff is entitled to such relief.” Winter v. Nat. Res. Def. Council, Inc., 555 U.S.
7, 22 (2008).
A plaintiff who seeks a preliminary injunction or temporary restraining order
must establish four elements: 1) that it likely will succeed on the merits; 2) that it
likely will to suffer irreparable harm in the absence of preliminary relief; 3) that
the balance of equities tips in its favor; and 4) that an injunction will serve the
public interest. See id. at 20.
Courts in the Ninth Circuit apply a sliding scale approach to preliminary
relief. See All. for the Wild Rockies v. Cottrell, 632 F.3d 1127, 1131 (9th Cir.
2011). The reviewing court must balance the elements “so that a stronger showing
of one element may offset a weaker showing of another.” Id. Even “serious
8

questions going to the merits and a balance of hardships that tips sharply towards
the plaintiff can support issuance of a preliminary injunction, so long as the
plaintiff also shows that there is a likelihood of irreparable injury and that the
injunction is in the public interest.” Id. at 1135. The public interest and the balance
of the equities factors merge when the government stands as a party. See Drakes
Bay Oyster Co. v. Jewell, 747 F.3d 1073, 1092 (9th Cir. 2014) (citing Nken v.
Holder, 556 U.S. 418, 435 (2009)).
Success on the merits
Plaintiffs fail at this juncture to show that they likely will succeed on the
merits. The Court retains serious questions regarding Plaintiffs’ legal claims.
Although the Court previously has ruled that Plaintiffs provide plausible claims
that survive a Motion to Dismiss, (Doc. 73), the complex and novel legal issues
raised in this dispute require further briefing for elucidation. The Court will seek
further briefing on the constitutional issues involved in this case. This kind of legal
uncertainty weighs heavily against granting preliminary injunctive relief. All. for
the Wild Rockies, 632 F.3d at 1135 (clarifying that “serious questions” regarding
legal merits can only be overcome when the balance of hardship “tips sharply” in
plaintiffs’ favor).

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Irreparable injury
Plaintiffs fail to show that they are likely to suffer irreparable injury in the
absence of preliminary relief. Plaintiffs’ filings blurred the lines between the
impact of the 1.2-mile border-crossing segment of the pipeline and the impact of
the full pipeline. For example, Plaintiffs noted that Keystone construction will
impact habitat for a variety of animals, including migratory birds, the American
Burying Beetle, and the Northern Long-Eared Bat. (Doc. 82-1 at 5–14). These
alleged injuries appear to occur entirely outside the 1.2-mile border-crossing
segment and would not arise from construction activities within the 1.2-mile
border-crossing segment. (Doc. 82-1 at 5–14; Doc. 92 at 17–18). Any alleged
irreparable injuries caused by construction outside the 1.2-mile border-crossing
segment go beyond the scope of the relief available because the permit only covers
the border segment. The proper “scope of injunctive relief is dictated by the extent
of the violation established.” Califano v. Yamasaki, 442 U.S. 682, 702 (1979). The
Court must set aside those injuries for purposes of injunctive relief analysis at this
point.
Plaintiffs claim two irreparable injuries within the 1.2-mile border-crossing
segment: potential oil leaks caused by the operation of the pipeline and the “social
costs” related to worker camps including increased drug use and sexual violence.
(Doc. 92 at 17). Each of these claimed injuries can result directly from the
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construction and eventual operation of the border crossing. Plaintiffs have not
demonstrated, however, the likelihood, rather than mere possibility, of injury.
Winter, 555 U.S. at 21 (directing that a plaintiff “must demonstrate a likelihood of
irreparable injury—not just a possibility—in order to obtain preliminary relief.”).
The pipeline project is not yet operational.
Finalized relief remains available before any risk resulting from pipeline
rupture may be realized. Keystone also will not operate in the immediate future
because the Court vacated certain permits required to complete Keystone in
another case. See Northern Plains Resource Council et al. v. U.S. Army Corps of
Engineers, et al., CV-19-44-GF-BMM (D. Mont. Apr. 15, 2020), 2020 WL
3638125; U.S. Army Corps of Engineers, et al. v. Northern Plains Resource
Council, et al., ___ S.Ct. ___, 2020 WL 3637662 (granting application for stay, in
part, and denying, in part). The 2019 Permit does not authorize worker camp
planning, placement, and operation. Plaintiffs cannot enjoin activities based on
irreparable injuries that occur outside the scope of the 2019 Permit. Cf. Save Our
Sanoran, Inc. v. Flowers, 408 F.3d 1113, 1123 (9th Cir. 2005) (“The authority to
enjoin development extends only so far as the Corps’ permitting authority.”).
Balance of equities and public interest
Both sides in this dispute can and do make valid arguments for their side in
the balance of equities and public interest. Plaintiffs point to the environmental
11

harms relating to construction and eventual operation of Keystone including
anthropogenic climate change. (Doc. 82-1 at 5–14; Doc. 91 at 19–20). TC Energy
points to significant investment made in the project over the last decade, potential
economic and tax revenue impacts, as well as current construction activities at the
border. (Doc. 86 at 27–28). Federal Defendants point to national interests in
supporting “energy security and maintaining strong bilateral relations with
Canada.” (Doc. 87 at 27). The weight of these factors remains unclear and fails to
compel the granting of preliminary relief.
TC Energy filed several status reports that detail its plans and
implementation of construction activities. (Docs. 62, 75, 83, 135). TC Energy
represented to the Court that it began construction of the border-crossing segment
of the pipeline on April 4, 2020. (Doc. 135-1 at 3). TC Energy further represented
that it anticipated completing the construction of that segment in May 2020. (Doc.
135-1 at 4). Construction will slow or stop with the winter months. The facts on the
ground suggest further ambiguity, and even potential mootness, when weighing the
equities involved in preliminary relief.
Preliminary injunctive relief represents an extraordinary remedy. Winter,
555 U.S. at 22. Plaintiffs carry the burden to provide a “clear showing” that they
are “entitled to such relief.” Id. Plaintiffs have failed to meet their burden because
serious merit questions remain, Plaintiffs have not shown irreparable harm, and the
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balance of equities and public interest provide ambiguous guidance. The Court will
deny Plaintiffs’ Renewed Motions for Preliminary Injunction and Temporary
Restraining Orders (Docs 82, 136) for the above reasons.
Motion for Leave to File Second and Third Supplemental
Complaints
Plaintiffs filed their Complaint on April 5, 2019. (Doc. 1). Plaintiffs then
filed their First Amended Complaint on July 18, 2019. (Doc. 37). Plaintiffs
represent that they submitted those amendments to “clarify[] certain allegations
and separately stat[e] a Third Claim for Relief alleging violation of Executive
Order 13,337.” (Doc. 109 at 3). Plaintiffs have since filed two additional motions
to amend their Complaint. (Docs. 108, 142).
Rule 15(a)(2) provides that leave to amend a complaint should be given
“when justice so requires.” Fed. R. Civ. P. 15(a)(2). The decision whether to grant
leave to amend “is entrusted to the sound discretion of the trial court.” Jordan v.
County of Los Angeles, 669 F.2d 1311, 1324 (9th Cir. 1982), vacated on other
grounds, 459 U.S. 810 (1982). Courts consider five factors when determining
whether to grant leave to amend: 1) bad faith; 2) undue delay; 3) prejudice to the
opposing party; 4) futility of the amendment; and 5) any previous amendments.
Johnson v. Buckley, 356 F.3d 1067, 1077 (9th Cir. 2004).

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Proposed Second Amended Complaint
President Trump issued Executive Order 13,867 (“2019 Executive Order”)
shortly after this litigation began. Issuance of Permits with Respect to Facilities
and Land Transportation Crossings at the International Boundaries of the United
States, Exec. Order 13,867, 84 Fed. Reg. 15,491 (April 10, 2019). The 2019
Executive Order revoked two previous Executive Orders that controlled the
presidential permitting process for pipeline border crossings. See id. at 15,492.
Plaintiffs filed a Motion for Leave to File a Second Amended Complaint to add the
2019 Executive Order to their Complaint. (Doc. 108).
The addition of a claim regarding the 2019 Executive Order would be futile
because it no longer remains at issue in this case. Plaintiffs’ original Complaint and
First Amended Complaint challenged President Trump’s issuance of the 2019
Permit. (Docs. 1, 37). The 2019 Permit was not issued pursuant to the 2019
Executive Order. Plaintiffs lack standing to challenge the 2019 Executive Order
because they have not been injured by the 2019 Executive Order.
Plaintiffs successfully claimed standing to challenge the 2019 Permit
because they “alleged sufficiently a concrete and particularized invasion of their
legally protected interests.” (Doc. 73 at 16–17 (citing Spokeo, Inc. v. Robins, ___
U.S. ___, ___, 136 S. Ct. 1540, 1548 (2016)). The 2019 Permit grants TC Energy
permission to “construct, connect, operate, and maintain pipeline facilities at the
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international border.” 84 Fed. Reg. at 13,101. The pipeline segment crosses “land
on which [the Plaintiffs] live, work, recreate, and otherwise enjoy.” (Doc. 73 at
17). It will “pass by or otherwise impact waters, habitat, and plant and animal
species.” Id. Plaintiffs cannot identify a similar set of injuries connected to the
2019 Executive Order that would satisfy the standing requirements.
Plaintiffs argue that should the Court invalidate the 2019 Permit, “it seems
likely that Trump would, in response, just reissue the 2019 Permit again” through
the 2019 Executive Order process. (Doc. 109 at 4). Plaintiffs could certainly
challenge the lawfulness of the 2019 Executive Order in such a case. This scenario
is not currently before the Court. Plaintiffs’ concern remains a theoretical injury,
rather than an injury-in-fact, as required to satisfy the standing requirements. See
Lujan v. Defs. of Wildlife, 504 U.S. 555, 559–61 (1992) (“The party invoking
federal jurisdiction bears the burden of establishing these elements.”).
Plaintiffs filed this Motion after a previous opportunity to add the 2019
Executive Order to their Complaint. Plaintiffs filed this motion almost a year after
President Trump issued the 2019 Executive Order. Plaintiffs already had amended
their Complaint at that point and failed to add the 2019 Executive Order in that
first amendment. “Undue delay is a valid reason for denying leave to amend.”
Texaco, Inc. v. Ponsoldt, 939 F.2d 794, 798 (9th Cir. 1991) (citation omitted); see
Komie v. Buehler Corp., 449 F.2d 644, 648 (9th Cir. 1971); but see Bowles v.
15

Reade, 198 F.3d 752, 758 (9th Cir. 1999) (“Undue delay by itself, however, is
insufficient to justify denying a motion to amend.”).
Plaintiffs repeatedly cite a previous Order of this Court that they claim
prompted their motion. (Doc 109 at 2, 4; Doc 122 at 2–5). The Court noted in that
Order: “If the 2019 Permit proves ultra vires because President Trump lacked the
inherent constitutional authority to issue the permit, the 2019 Executive Order
likely would be unlawful for similar reasons. Plaintiffs’ claims currently before the
Court do not directly present the question of whether the 2019 Executive Order
proves lawful.” (Doc. 73 at 37). Plaintiff seems to have overread the Court’s dicta.
The Court did not intend to invite the parties to expand the scope of litigation at
this late stage.
The Court will reject the Motion for Leave to File a Second Amended
Complaint (Doc. 108) due to the futility of amendment, Plaintiffs’ undue delay,
and Plaintiffs’ previous opportunity to amend the Complaint. See Johnson, 356
F.3d at 1077.
Proposed Third Amended Complaint
TC Energy sought and received a right-of-way permit from BLM for the 1.2mile border-crossing segment as well as approximately 43 other miles of federal
land. See U.S. Bureau of Land Management, Record of Decision: Keystone XL
Pipeline Project Decision to Grant Right-of-Way and Temporary Use Permit on
16

Federally Administered Land, DOI-BLM-MT-C020-2020-0022-OTHER_NEPA
(Jan. 22, 2020). BLM issued their record of decision (“2020 ROD”) regarding the
Keystone right-of-way on January 22, 2020. Id. The 2020 ROD relies, in turn, on
the findings of a Final Supplemental Environmental Impact Statement for the
Keystone XL Project (“2019 FSEIS”), 84 Fed. Reg. 70,187, 70,188 (Dec. 20,
2019), in response to a previous Order by the Court. See IEN v. U.S. Department of
State, et al., 347 F.Supp.3d 561 (D. Mont. 2018). Plaintiffs filed a Motion for
Leave to File a Third Amended Complaint to add claims regarding the 2020 ROD
and 2019 FSEIS to their Complaint. (Doc. 142).
Plaintiffs seek to add these new claims four months after the existing claims
had been briefed, argued, and submitted to the Court for final ruling. Their motion
also comes nine months after BLM issued the 2019 FEIS and seven months after
BLM issued the 2020 ROD. Such undue delay in seeking amendment weighs
against allowing leave. Schlacter-Jones v. Gen. Telephone of Cal., 936 F.2d 435,
443 (9th Cir. 1991) (noting that timing of a motion to amend after summary
judgment brief had been fully briefed weighed heavily against allowing leave to
amend complaint); see also Kaplan v. Rose, 49 F.3d 1363, 1370 (9th Cir. 1994)
(upholding the denial of a motion to amend where leave was sought at the
summary judgment stage). The proposed amendment would additionally delay the
resolution of existing claims.
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The addition of new claims would unfairly prejudice Federal Defendants and
TC Energy. “The purpose of Rule 15(d) is to promote as complete an adjudication
of the dispute between the parties as possible by allowing the addition of claims
which arise after the initial pleadings are filed.” Keith v. Volpe, 858 F.2d 467, 473–
74 (9th Cir. 1988) (quoting William Inglis & Sons Baking Co. v. ITT Cont’l Baking
Co., 668 F.2d 1014, 1057 (9th Cir. 1981)). “While leave to permit supplemental
pleading is ‘favored,’ Keith, 858 F.2d at 473, it cannot be used to introduce a
‘separate, distinct and new cause of action.’” Planned Parenthood of S. Arizona v.
Neely, 130 F.3d 400, 402 (9th Cir. 1997) (per curiam) (citation omitted). The
introduction of new claims at this stage would require the introduction of a new
administrative record, new briefing, and new argument. These prejudicial burdens
at this late stage of the litigation weigh against granting leave.
Judicial economy further supports denial of this motion for leave. The 2019
FEIS and 2020 ROD are already the subjects of two other lawsuits before the
Court. See Bold All. v. U.S. Dep’t of the Interior, 4:20-cv-00059-BMM-JTJ (D.
Mont.); Assiniboine & Sioux Tribes of the Ford Peck Indian Rsrv. v. U.S. Dep’t of
the Interior, 4:20-cv-00044-BMM-JTJ (D. Mont.). Those cases remain in the early
stages of litigations. Plaintiffs may seek to intervene in one of these two cases or
may file a separate action that can be heard on similar schedule to these existing

18

lawsuits. Denial of this motion will not cause undue burden or prejudice to
Plaintiffs under these circumstances.
The Court will reject the Motion for Leave to File a Third Amended
Complaint (Doc. 142) to prevent undue delay and prejudice, and to promote
judicial economy. See Johnson, 356 F.3d at 1077.
III.

Additional Briefing on Authority for the 2017 Presidential Permit
Plaintiffs raised three claims in their Complaint: that President Trump’s

issuance of the 2019 Permit 1) violated the Property Clause of the U.S.
Constitution; 2) violated the Commerce Clause of the U.S. Constitution; and 3)
violated Executive Order 13,337. (Doc. 37 at 24, 27, 31). These claims implicate
novel and complex separation of powers questions. The Court earlier sought
supplemental briefing on separation of powers among other issues. (Doc. 93). The
Court now seeks to narrow the constitutional analysis. The Court will require
further briefing, however, in an effort to distinguish the exact contours of
presidential and congressional authority over pipeline border-crossing permits.
The Youngstown Framework
The President wields significant authority, particularly in the “era of
presidential administration.” Elena Kagan, Presidential Administration, 114 Harv.
L. Rev. 2245, 2246 (2001). This significant authority comes with critical
limitations intended to safeguard our constitutional system—particularly when the
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President takes unilateral action. See Youngstown Sheet & Tube v. Sawyer, 343
U.S. 579, 634 (1952) (Jackson, J., concurring) (cautioning the dangers of a
strengthened executive on the “balanced power structure of our Republic”). These
safeguards include the separation of powers between the coordinate branches, the
qualified delegation of authority from Congress, and federalism. See, e.g.,
Mistretta v. United States, 488 U.S. 361, 380 (1989) (noting that the constitutional
principle of separation of powers embodies “the central judgment of the Framers of
the Constitution that, within our political scheme, the separation of governmental
powers into three coordinate Branches is essential to the preservation of liberty” in
order to preventing aggrandizement by one branch encroaching into the sphere of
authority of another); Buckley v. Valeo, 424 U.S. 1, 122 (1976) (per curiam) (“The
Framers regarded the checks and balances that they had built into the tripartite
Federal Government as a self-executing safeguard against the encroachment or
aggrandizement of one branch at the expense of the other.”).
A court may determine whether a unilateral presidential action went beyond
the bounds of the executive power and infringed on the enumerated powers of
Congress. Even where the President has broad discretion over an issue, “that
discretion is not boundless” and “may not transgress constitutional limitations.”
Abourezk v. Reagan, 785 F.2d 1043, 1061 (D.C. Cir. 1986). It remains “the duty of
the courts, in cases properly before them, to say where th[e] . . . constitutional
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boundaries lie.” Id. Justice Jackson established a three-category framework to
assess the constitutionality of an executive action. See Youngstown Sheet & Tube,
343 U.S. at 635–37 (Jackson, J., concurring).
In the first category, “[w]hen the President acts pursuant to an express or
implied authorization [from Congress], his authority is at its maximum.” Id. at 635.
When Congress legislates to give the President authorization to act on a subject,
the President personifies “the federal sovereignty,” and his actions are
presumptively valid. Id. at 636–37. Few cases apply this first category. In those
cases that do exist, the U.S. Supreme Court tends to find both express and implied
authorization as reinforcing factors placing the executive action into this category.
See, e.g., Trump v. Hawaii, 138 S. Ct. 2392, 2407–08 (2018); Dames & Moore v.
Regan, 453 U.S. 670, 669 (1981).
In the second category, when the “President acts in absence of either a
congressional grant or denial of authority” relying on “his own independent
powers” then “congressional inertia, indifference or quiescence may sometimes, at
least as a practical matter, enable, if not invite, measures on independent
presidential responsibility.” Youngstown, 343 U.S. at 637. Still fewer cases exist
involving this second category of executive action. See, e.g., Zivotofsky v. Kerry,
576 U.S. 1059, 1088–94 (2015); United States v. Midwest Oil Co., 236 U.S. 459,
474 (1915).
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In the third category, “[w]hen the President takes measures incompatible
with the expressed or implied will of Congress, his power is at its lowest ebb.”
Youngstown, 343 U.S. at 637. In such a case, Presidents may rely only on their own
independent power, after “subtraction of such powers as Congress may have over
the subject.” Id. at 639. Several examples of this third category exist. See, e.g.,
Zivotofsky v. Kerry, 576 U.S. 1059, 1088–94 (2015); Medellín v. Texas, 552 U.S.
491, 525–29 (2008).
The three Youngstown categories prove useful, but they serve only as guides.
Executive actions “in any particular instance fall[] not neatly in one of three
pigeonholes, but rather at some point along a spectrum running from explicit
congressional authorization to explicit congressional prohibition.” Dames & Moore
v. Regan, 453 U.S. 670, 669 (1981). “[T]he great ordinances of the Constitution do
not establish and divide fields of black and white.” Id. at 669 (quoting Springer v.
Philippine Islands, 277 U.S. 189, 209 (1928) (Holmes, J., dissenting).
In separation of powers cases, the U.S. Supreme Court “has often ‘put
significant weight upon historical practice.’” Zivotofsky, 135 S. Ct. at 2091
(quoting NLRB v. Noel Canning, 134 S. Ct. 2550, 2559 (2014)). The history of the
pipeline permitting process involved a string of executive actions. The
constitutionality of any particular executive action must be analyzed in its own

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context, and each executive decision over the history of a particular policy may fall
at a unique point on the Youngstown framework spectrum.
The Supreme Court provided a model for historical analysis of a particular
power in Zivotofsky. Justice Anthony Kennedy systematically analyzed the history
of the legislative and executive contest over the power to recognize foreign
nations. See Zivotofsky, 576 U.S. at 23-28. Justice Kennedy meticulously
categorized a series of historical recognition decisions within the Youngstown
framework in order to contextualize the particular recognition decision before the
Supreme Court. See id. This model for separation of powers analysis proves useful
and applicable to the case before the Court today.
Supplemental Briefing
The history of presidential permits for pipelines—and for Keystone in
particular—provides a new example of historical inter-branch conflict. This Court
previously sought additional briefing to inform its analysis of the separations of
powers questions implicated in this case. (Doc. 74). The Court now seeks
additional briefing with more specific direction.
The Court seeks briefing on the application of Youngstown to the timeline of
pipeline border-crossing permits. The Parties should assume that the Foreign
Commerce Clause, the Property Clause, and the various executive and legislative
powers relating to foreign affairs remain relevant to this analysis. (Doc. 73 at 21–
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34). The Parties should center analysis on border-crossing pipeline permits, not
border-crossing permits in general.
1. Where on the Youngstown spectrum do each of the following individual
executive actions lie:
a. Issuance of pre-1968 cross-border pipeline permits;
b. Issuance of Executive Order 11423, Providing for the Performance of
Certain Functions Heretofore Performed by the President with
Respect to Certain Facilities Constructed and Maintained on the
Borders of the United States, Exec. Order 11423, 33 Fed. Reg. 11741
(Aug. 20, 1968);
c. Executive Order 13,337, Issuance of Permits With Respect to Certain
Energy-Related Facilities and Land Transportation Crossings on the
International Boundaries of the United States, Exec. Order No.
13,337, 69 Fed. Reg. 25299 (April 30, 2004);
d. State Department Denial of TC Energy’s application following
Congress’ passage of the Temporary Payroll Tax Cut Continuation
Act (“TPTCCA”), Pub. L. No. 112-78, 125 Stat. 1280 (December 23,
2011);

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e. President Barack Obama’s veto of the Keystone XL Pipeline
Approval Act. Veto Message to the Senate: S. 1, Keystone XL
Pipeline Approval Act, 2015 WL 758544 (2015); and
f. President Donald Trump’s issuance of the 2019 Permit.
2. Address the following additional questions that will inform the Court’s
Youngstown analysis:
a. Did TPTCCA endorse the EO 13,337 process generally?
b. Did TPTCCA endorse the EO 13,337 process only for Keystone?
c. Assuming TPTCCA endorsed the EO 13,337 process for Keystone,
how could TC Energy obtain a permit once President Obama denied
the permit?
d. How should the Court interpret the passage of the Keystone XL
Pipeline Approval Act?
ORDER
Accordingly, IT IS ORDERED that:
• Plaintiffs’ Renewed Motion for Preliminary Injunction and
Application for Temporary Restraining Order (Doc. 82) is DENIED;
• Plaintiffs’ Renewed Request for a Preliminary Injunction and
Application for Temporary Restraining Order (Doc. 136) is DENIED;

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• Plaintiffs’ Motion for leave to file a Second Amended Complaint
(Doc. 108) is DENIED;
• Plaintiffs’ motion for leave to file a Third Amended Complaint (Doc.
142) is DENIED;
• The Parties shall file simultaneous briefing, not to exceed 10,000
words, on the issues listed in Part III.b of this Order within 30 days of
the issuance of this Order.
Dated the 16th day of October, 2020.

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