Shaik v. Certain Underwriters at Lloyd's of London et al

IN THE UNITED STATES DISTRICT COURT
FOR THE EASTERN DISTRICT OF OKLAHOMA
ZAK SHAIK,
Plaintiff,
v.
CERTAIN 	UNDERWRITERS 	AT 	LOYD’S
OF LONDON, et al.,
Defendants.
Civil No. 24-271 (FAB)
MEMORANDUM 	AND 	ORDER
BESOSA, Senior District Judge.1
Before 	the 	Court 	is 	plaintiff 	Zak 	Shaik 	(“plaintiff”)’s
motion 	to 	alter 	or 	amend 	judgment. 	(Docket 	No. 	76.) 	For 	the
reasons set forth below, plaintiff’s motion is DENIED.
I. 	Background
On March 10, 2023, plaintiff purchased property insurance for
several 	properties 	he 	owned 	in 	Sulphur, 	Oklahoma. 	(Docket 	No. 	2
at 	p. 	3.) 	Defendant 	“Certain 	Underwriters 	at 	Lloyd’s 	of 	London”
(“Lloyd’s) 	served 	as 	the 	underwriter. 	(Docket 	No. 	54 	at 	p. 	4.)
Defendant 	Millennial 	Specialty 	Insurance, 	LLC 	(“Millennial”)
served 	as 	the 	insurance 	agent. 	(Docket 	No. 	19 	at 	pp. 	4-5.)
Defendant 	Baldwin 	Insurance 	Group 	Holdings, 	LLC 	(“Baldwin,” 	and
1 Of the District of Puerto Rico, sitting by designation.
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Civil No. 24-271 (FAB)___ 	__ 	2
collectively with Lloyd’s and Millennial, the “defendants”) is the
parent company of Millennium. (Docket No. 21 at pp. 5-6.)
On 	April 	26, 	2024, 	a 	tornado 	struck 	Sulphur 	and 	allegedly
caused 	extensive 	damage 	to 	plaintiff’s 	properties. 	Id. 	at 	p. 	4.
He 	requested 	compensation 	from 	the 	defendants 	pursuant 	to 	his
insurance 	policies 	but 	defendants 	refused, 	claiming 	that 	the
policies had been cancelled and that his coverage had expired due
to 	his 	failure 	to 	pay 	his 	premiums. 	Id. 	at 	pp. 	4-5. 	Plaintiff
sued 	defendants 	for 	breach 	of 	contract 	and 	breach 	of 	the 	duty 	of
good 	faith, 	alleging 	wrongful 	denial 	of 	coverage. 	Id. 	at 	pp. 	6-
8. 	Defendants moved to dismiss plaintiff’s complaint, citing the
fact that he had failed to show a covered loss. 	(Docket Nos. 52,
53, 	54.) 	While 	the 	motions 	to 	dismiss 	were 	pending, 	plaintiff
requested 	leave 	to 	amend 	his 	complaint. 	(Docket 	No. 	70.) 	The
Court, 	however, 	granted 	defendants’ 	motions 	and 	dismissed
plaintiff’s 	claims 	with 	prejudice. 	(Docket 	No. 	71.) 	The 	Court
found that plaintiff’s loss unequivocally occurred outside of the
policy 	coverage 	period, 	and 	that 	he 	presented 	no 	basis 	for 	the
Court 	to 	conclude 	that 	his 	coverage 	continued 	after 	that 	period.
Id. 	at 	pp. 	7-8. 	Without 	specifically 	addressing 	plaintiff’s
proposed 	amended 	complaint, 	the 	Court 	found 	that 	any 	attempt 	to
amend 	it 	would 	be 	futile. 	Id. 	at 	pp. 	8-9. 	The 	Court 	then
separately 	denied 	plaintiff’s 	outstanding 	request 	to 	amend 	the
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Civil No. 24-271 (FAB)___ 	__ 	3
complaint, 	referring 	to 	its 	previously-issued 	Opinion 	and 	Order.
See 	Docket 	No. 	72. 	On 	May 	22, 	2026, 	judgment 	was 	entered
dismissing plaintiff’s claims with prejudice. 	(Docket No. 73.)
On 	May 	28, 	2026, 	plaintiff 	requested 	to 	alter 	or 	amend 	the
judgment. 	(Docket 	No. 	76.) 	He 	argues 	that 	the 	Court’s 	decision
to 	dismiss 	his 	claims 	with 	prejudice 	was 	procedurally 	improper
because, at the time of judgment, he had an outstanding motion to
amend his complaint which the Court had not ruled upon. 	He claims
that this error justifies relief pursuant to Federal Rule of Civil
Procedure 	59(e) 	(“Rule 	59(e)”). 	Defendants 	disagree, 	asserting
that 	plaintiff’s 	argument 	does 	not 	fit 	within 	the 	scope 	of
permissible 	bases 	for 	relief 	pursuant 	to 	Rule 	59(e). 	(Docket
No. 80.) 	Defendants also argue that the Court’s finding that any
motion 	to 	amend 	would 	be 	futile 	substantively 	forecloses 	his
argument and shows that granting his motion for relief would be a
waste of judicial resources.
II. 	Legal Standard
Pursuant to Rule 59(e), a party may move to alter or amend a
judgment by filing a motion no later than 28 days after the entry
of the judgment. 	“Grounds for granting a Rule 59(e) motion include
(1) an intervening change in the controlling law, (2) new evidence
previously unavailable, and (3) the need to correct clear error or
prevent 	manifest 	injustice.” 	Monge 	v. 	RG 	Petro-Mach. 	Group 	Co.
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Civil No. 24-271 (FAB)___ 	__ 	4
Ltd., 	701 	F.3d 	598, 	611 	(10th 	Cir. 	2012) 	(quoting 	Somerlott 	v.
Cherokee Nation Distributors, Inc., 686 F.3d 1144, 1153 (10th Cir.
2012)) 	(quotation 	marks 	omitted). 	“[A] 	Rule 	59(e) 	motion 	is 	not
appropriate 	to 	revisit 	issues 	already 	addressed 	or 	advance
arguments 	that 	could 	have 	been 	raised 	in 	prior 	briefing.” 	Id.
(internal quotation marks omitted).
A 	pro 	se 	litigant’s 	pleadings 	should 	be 	held 	“to 	less
stringent 	standards 	than 	formal 	pleadings 	drafted 	by 	lawyers.”
Tatten v. City & Cty. of Denver, 730 F. App’x 620, 624 (10th Cir.
2018) 	(quoting 	Haines 	v. 	Kerner, 	404 	U.S. 	519, 	520 	(1972)). 	On
the 	other 	hand, 	“a 	pro 	se 	litigant’s 	‘conclusory 	allegations
without 	supporting 	factual 	averments 	are 	insufficient 	to 	state 	a
claim 	on 	which 	relief 	can 	be 	based.’” 	West 	v. 	United 	States,
No. 25-3082, 2025 U.S. App. LEXIS 24165, at *5 (10th Cir. Sept. 18,
2025) 	(quoting 	Hall 	v. 	Bellmon, 	935 	F.2d 	1106, 	1110 	(10th 	Cir.
1991)). 	It 	is 	not 	“the 	proper 	function 	of 	the 	district 	court 	to
assume 	the 	role 	of 	advocate 	for 	the 	pro 	se 	litigant.” 	Hall, 	935
F.2d at 1110.
III. Discussion
Plaintiff argues that the Court’s dismissal of his complaint
while 	his 	motion 	to 	amend 	his 	complaint 	was 	pending 	was 	an 	error
deserving 	relief 	from 	the 	judgment 	pursuant 	to 	Rule 	59(e). 	The
Court’s 	Opinion 	and 	Order, 	however, 	addressed 	the 	possibility 	of
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Civil No. 24-271 (FAB)___ 	__ 	5
amending 	the 	complaint, 	finding 	that 	doing 	so 	would 	be 	futile
because any amended complaint would also be subject to dismissal.
The 	question 	of 	whether 	the 	requested 	amendment 	would 	be 	futile
was also discussed in the report and recommendation on the motions
to dismiss issued by magistrate judge Gerald L. Jackson; plaintiff
subsequently 	objected 	to 	the 	magistrate 	judge’s 	finding 	of
futility. 	Accordingly, 	raising 	the 	possibility 	of 	amendment
revisits 	an 	issue 	already 	addressed 	and 	is 	therefore 	an
inappropriate ground for Rule 59(e) relief.
The 	Court 	acknowledges, 	however, 	that 	the 	Opinion 	and 	Order
did not squarely address the merits of plaintiff’s proposed amended
complaint. 	If the proposed amended complaint would not be subject
to 	dismissal, 	the 	Court’s 	futility 	conclusion 	would 	be 	a 	clear
error 	whose 	correction 	would 	justify 	relief 	under 	Rule 	59(e).
Accordingly, for good measure, the Court will consider whether the
proposed amended complaint states a claim.
Plaintiff’s 	proposed 	amended 	complaint 	was 	filed 	on 	May 	18,
2026 	and, 	as 	he 	points 	out 	in 	his 	request 	to 	amend, 	was 	written
with 	an 	eye 	toward 	resolving 	the 	issues 	identified 	in 	the
magistrate 	judge’s 	report 	and 	recommendation. 	See 	Docket 	No. 	70
at p. 2. 	The Court can discern two distinct theories of insurance
coverage 	from 	the 	proposed 	amended 	complaint. 	First, 	plaintiff
alleges that the policies provide coverage based on a “continuous
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Civil No. 24-271 (FAB)___ 	__ 	6
reporting, 	scheduling, 	and 	premium-based 	system,” 	and 	not 	on 	the
coverage period. 	Second, he alleges that coverage continued after
the 	expiration 	date 	because 	the 	policies 	were 	not 	properly
cancelled, an argument that was raised in his original complaint.
Plaintiff’s 	first 	argument 	fails 	to 	allege 	a 	covered 	loss
with 	sufficient 	plausibility 	to 	avoid 	dismissal. 	He 	argues 	that
the 	policy 	operates 	to 	provide 	coverage 	outside 	of 	the 	coverage
period 	based 	on 	what 	he 	calls 	the 	“continuous 	reporting,
scheduling, 	and 	premium-based 	system.” 	This 	theory 	is 	not
explained 	clearly 	or 	in 	detail 	- 	all 	that 	the 	Court 	can 	say
decisively about it is that it somehow operates to provide coverage
after 	the 	policy’s 	expiration 	date. 	Nor 	does 	plaintiff 	back 	up
his theory with any citation to the policy language itself.2 	The
Court 	considers 	this 	theory 	a 	conclusory 	allegation 	of 	coverage
couched as a factual assertion that need not be credited as true.
See 	Ashcroft 	v. 	Iqbal, 	556 	U.S. 	662, 	678 	(2009) 	(courts 	“are 	not
bound 	to 	accept 	as 	true 	a 	legal 	conclusion 	couched 	as 	a 	factual
allegation”).
Plaintiff’s second argument is that coverage continued after
expiration 	because 	the 	policies 	were 	improperly 	terminated. 	The
policies were allegedly terminated in 2023, before the expiry date,
2 The Court never received a copy of the full policy text from any of the parties
at any stage of the case.
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because plaintiff failed to pay his insurance premiums.3 	Plaintiff
alleges 	that 	the 	defendants 	failed 	to 	comply 	with 	Oklahoma 	law
when cancelling the policy. 	He does not, however, provide a clear
account 	of 	exactly 	how 	defendants 	purportedly 	failed 	to 	comply
with Oklahoma law. 	He seems to allege that he never received the
notice 	of 	cancellation, 	which 	is 	a 	prerequisite 	to 	cancelling 	an
insurance 	policy 	under 	Oklahoma 	law. 	See 	Owens 	v. 	Equity 	Ins.
Co., 	No. 	23-212-JWB, 	2025 	U.S. 	Dist. 	LEXIS 	266105, 	at 	*6-7 	(N.D.
Okla. Jul. 31, 2025) (“Under Oklahoma law, to cancel a policy for
nonpayment, the ‘insurer must wait until the insured fails to make
a 	scheduled 	payment’ 	and 	then 	give 	notice 	in 	accordance 	with 	the
policy.”) 	(quoting 	Bufogle 	v. 	Equity 	Ins. 	Co., 	No. 	11-CV-0657,
2012 	U.S. 	Dist. 	LEXIS 	118481, 	at 	*4 	(N.D. 	Okla. 	Aug. 	22, 	2012)).
Plaintiff, however, contradicts himself on this point on numerous
occasions 	in 	his 	briefs. 	See, 	e.g., 	Docket 	No. 	2 	at 	p. 	4
(explaining 	how 	plaintiff’s 	coverage 	demand 	letter 	to 	defendants
3 Defendants attached the notices of cancellation to their motion to dismiss.
See Docket No. 54-1 at p. 5; 54-2 at p. 5; 54-3 at p. 5; 54-4 at p. 5; 54-5 at
p. 5; 54-6 at p. 5. 	The magistrate judge declined to consider the notices after
concluding they were outside the scope of the complaint. 	See Docket No. 59 at
p. 9 n. 3. 	The Court disagrees - plaintiff’s argument for continuing coverage,
present on the face of both the original and proposed amended complaint, is
that these notices either never existed, were not sent to him, or were legally
insufficient 	under 	Oklahoma 	law. 	Consequently, 	the 	notices 	are 	“central 	to
plaintiff’s claim, [and] a defendant may submit an indisputably authentic copy
to the court to be considered on a motion to dismiss.” 	GFF Corp. v. Associated
Wholesale Grocers, 130 F.3d 1381, 1384 (10th Cir. 1997). 	Although plaintiff
challenges whether the notices were legally sufficient, he does not challenge
their authenticity.
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Civil No. 24-271 (FAB)___ 	__ 	8
raised issues with the notices of cancellation, suggesting he did
in fact receive the notices); Docket No. 32 at p. 3 (asserting an
equitable 	estoppel 	claim 	based 	on 	defendants 	“[s]ending
inconsistent 	cancellation 	notices.”) 	Even 	his 	affirmative
statements 	that 	he 	never 	received 	the 	notice 	are 	themselves
generally couched in ambiguous qualifying language. 	For example,
in 	his 	proposed 	amended 	complaint, 	he 	does 	not 	simply 	state 	that
he never received the cancellation notice, but instead states that
“[n]o 	valid 	cancellation 	or 	non-renewal 	notice 	was 	issued[,]”
without explaining what he means by “valid.” 	(Docket No. 70-2 at
p. 	3) 	(emphasis 	added). 	Inconsistent 	allegations 	can 	be 	fairly
interpreted 	as 	implausible 	and 	need 	not 	be 	credited. 	See 	Pinto-
Rios v. Brown, No. 20-cv-3698-RMR-JPO, 2024 U.S. Dist. LEXIS 52847,
at 	*17 	(D. 	Colo. 	Mar. 	25, 	2024) 	(“The 	Court 	is 	not 	required 	to
give 	credence 	to 	[] 	inconsistent 	allegations, 	and 	it 	does 	not 	do
so here.”)
Accordingly, 	as 	was 	the 	case 	with 	his 	original 	complaint,
plaintiff’s proposed amended complaint fails to state a claim upon
which relief can be granted. 	This being the case, plaintiff does
not 	have 	a 	persuasive 	reason 	for 	vacating 	the 	judgment 	under
Rule 59(e).
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IV. 	Conclusion
For the reasons set forth above, plaintiff’s motion to alter
or amend the judgment is DENIED. 	(Docket No. 76.)
IT IS SO ORDERED.
San Juan, Puerto Rico, June 18, 2026.
s/ Francisco A. Besosa
FRANCISCO A. BESOSA
SENIOR UNITED STATES DISTRICT JUDGE
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