State of Minnesota, Respondent,

This opinion is nonprecedential except as provided by
Minn. R. Civ. App. P. 136.01, subd. 1(c).

STATE OF MINNESOTA
IN COURT OF APPEALS
A25-0441

State of Minnesota,
Respondent,

vs.

Ishamel Portwood Middlebrook,
Appellant.

Filed April 27, 2026
Affirmed
Bentley, Judge

Hennepin County District Court
File No. 27-CR-24-16542

Keith Ellison, Attorney General, St. Paul, Minnesota; and

Mary F. Moriarty, Hennepin County Attorney, Britta Nicholson, Assistant County
Attorney, Minneapolis, Minnesota (for respondent)

Cathryn Middlebrook, Chief Appellate Public Defender, Julie Loftus Nelson, Assistant
Public Defender, Bekah Muta (certified law student practitioner), St. Paul, Minnesota (for
appellant)

Considered and decided by Ede, Presiding Judge; Bentley, Judge; and Smith, John,
Judge.
∗

∗ Retired judge of the Minnesota Court of Appeals, serving by appointment pursuant to
Minn. Const. art. VI, § 10.
2
NONPRECEDENTIAL OPINION
BENTLEY, Judge
Appellant seeks reversal of his convictions for first-degree sale of a controlled
substance and fifth-degree possession of a controlled substance. He argues that the district
court erred in denying his motion to suppress evidence seized following a warrantless arrest
and a subsequent warrantless search of his person. Appellant also contends that he was
denied effective assistance of counsel because his trial attorney did not challenge the
warrantless search of his car. Because we conclude that officers had probable cause to
arrest appellant and conduct a search of his person incident to that arrest, and that appellant
has not established an ineffective-assistance-of-counsel claim, we affirm.
FACTS
The evidence admitted at a hearing on appellant Ishamel Portwood Middlebrook’s
motion to suppress included officer testimony and footage from Minneapolis’s Milestone
camera system1 and from the arresting officer’s body-worn camera.
Around midnight on July 19, 2024, Officer D. was monitoring a live video feed of
an intersection near a park in Minneapolis. 2 He testified that the area is an open-air drug

1 Officer testimony described the Milestone camera system as “[a] n extensive camera
network throughout the city of Minneapolis,” covering a large portion of “main
thoroughfares” downtown, which provides police with a live feed and the ability for
playback.

2 We refer to the officers by their initials instead of their full names in accordance with our
rules of public access. See Minn. R. Pub. Access to Recs. of Jud. Branch 8, subd. 2(b)
(recommending that appellate opinions limit disclosure of witness identities “to what is
necessary and relevant”).
3
market “where [one] can daily observe people using and selling narcotics.” Officer D.
observed a red vehicle that was registered to Middlebrook Management LLC . Officer D.
was familiar with the vehicle and Middlebrook from prior investigations and recognized
him in the driver’s seat.
At one point, Officer D. observed that “another male approached the window,
reached inside, and appeared to hand something to [Middlebrook] and then stood by
until [Middlebrook] paid him something back, and then he walked off.” Although the
actual exchange was not visible in the footage, Officer D. assumed “based on [his] training
and experience that there was a hand-to -hand transaction that took place in the car.”
Officer D. then observed the individual, who “appeared to be clutching something” in “the
hand that he put inside the vehicle,” walk away and join a group of people, “where he
removed tinfoil from his pocket.” The group “[could] be seen smoking what appeared to
be narcotics.”
Officer D. asked Officer P. to review the footage. Officer P. was also familiar with
Middlebrook based on “a prior narcotics and weapons investigation.” Officer P. explained
that, for over an hour, they “continued to monitor and review the milestone camera just to
confirm what [they] observed initially.” The Milestone-camera footage shows several other
people approaching Middlebrook’s car and interacting with him during that timeframe.
When asked at the evidentiary hearing if he saw anything exchanged hand-to-hand,
Officer P. said he did not, but he noted that, “[w]hen we saw the people interacting with
[Middlebrook], the hand to hand or the interaction was obstructed by the dash of the
vehicle.” The officers acknowledged that they could not see what was in the hand of the
4
individual who later appeared to smoke narcotics, and Officer D. conceded that it was
“possible” that the narcotics the individual used came from someone else in the group,
though he “didn’t see anyone hand anything else to him.”
The officers left the precinct, approached Middlebrook’s car, and placed him under
arrest. Officer P. conducted an initial search of Middlebrook’s person, during which he
found nothing, and then placed Middlebrook in the squad car. The officers searched the
vehicle and located a scale with a white powdery residue on it and two bags containing a
“green leafy substance” with a “strong chemical smell” that Officer P. believed, based on
his experience working in narcotics, was K2, “a synthetic cannabinoid or THC.”
At that point, Officer P. conducted a second search of Middlebrook’s person
because of his “knowledge from prior narcotics investigations that narcotics dealers will
conceal narcotics on their person.” During that second search, Officer P. found over 300
“suspected counterfeit oxycodone pills,” which field-tested positive for fentanyl, and a bag
with a “white powdery substance,” which field-tested positive for cocaine.
Respondent State of Minnesota charged Middlebrook with first-degree sale of a
controlled substance— heroin or fentanyl, in violation of Minn. Stat. § 152.021, subd. 1(3)
(Supp. 2023 ); first-degree possession of a controlled substance— heroin or fentanyl, in
violation of Minn. Stat. § 152.021, subd. 2(a)(3) (Supp. 2023 ); and two counts of fifth -
degree possession of a controlled substance, in violation of Minn. Stat. § 152.025, subd.
2(1) (Supp. 2023). Middlebrook moved to suppress the evidence discovered in the
warrantless search of his car and the second search of his person, arguing that officers
lacked reasonable, articulable suspicion, and, by extension, probable cause, to stop and
5
arrest Middlebrook in the first instance, and that they lacked probable cause to search his
person a second time.
The district court denied the motion to suppress and gave a verbal explanation of its
decision at a subsequent hearing. The district court applied a reasonable-suspicion analysis
to the initial stop and search of Middlebrook’s person, determining that the “officers had
reasonable, articulable suspicion to stop and search defendant based on the totality of the
circumstances.” And the court determined with respect to the second search of
Middlebrook’s person that the officers “had probable cause to arrest and search defendant
based on the totality of circumstances.”
In support of its decision that the officers had reasonable, articulable suspicion for
an initial stop, the district court found that
the defendant and his vehicle were known to the officers based
on prior narcotic investigations; the defendant was parked in
what the officers considered or testified to be an open drug
area; the defendant was parked in this area for approximately
an hour and a half; several individuals were observed
approaching the defendant’s vehicle and engaging in
suspicious activity, which reasonably could be inferred, based
on the officers’ training and experience, to be associated with
drug sale activity; lastly, the defendant was observed engaging
in a hand-to-hand transaction with an unknown male who
walked a short distance away and began to visibly smoke
narcotics with other known individuals immediately after
engaging in what officers believed to be a hand-to- hand
transaction with the defendant.[3]

3 Later in its decision, when it determined that the officers had probable cause to conduct
a second search of Middlebrook’s person as a search incident to arrest, the district court
also considered evidence discovered in the warrantless search of the car. We do not
consider that evidence in our analysis because of our conclusion that the officers had
probable cause to arrest Middlebrook and to search his person at the time of the initial stop.
We consider only the circumstances known to the officers at that time.
6

The case proceeded to trial, and a jury found Middlebrook guilty on all counts. The
district court adjudicated Middlebrook guilty of first -degree sale of fentanyl and fifth-
degree possession of cocaine, but it did not adjudicate the other counts because they
constituted lesser-included offenses. The court imposed a sentence of 128 months’
imprisonment for the first-degree sale count. It did not impose a sentence for the cocaine-
possession charge because the district court concluded that it arose from the same
behavioral incident or course of conduct as the first-degree count.
Middlebrook appeals.
DECISION
Middlebrook’s arguments on appeal focus on the district court’s reasonable-
suspicion analysis but, as the state points out, the officers did not conduct a Terry stop4
when they first approached Middlebrook—they arrested him. Therefore, the lawfulness of
his arrest and the subsequent searches of his person turns on whether the officers had
probable cause to arrest him at that time, not whether they had reasonable, articulable
suspicion to conduct a Terry stop or whether they reasonably expanded the scope of a Terry
stop when they searched Middlebrook’s car and conducted a second search of his person.
Indeed, Middlebrook argued in the district court proceedings that the officers did not have

4 A Terry stop “allows a police officer to stop and temporarily seize a person to investigate
that person for criminal wrongdoing if the officer reasonably suspects that person of
criminal activity.” State v. Diede, 795 N.W.2d 836, 842 (Minn. 2011) (quotation omitted)
(citing Terry v. Ohio, 392 U.S. 1 (1968)).
7
probable cause to arrest him at the time of the initial stop, and he asserts the same in his
appellate reply brief when responding to the state’s argument.
Even though the district court analyzed the initial stop under the reasonable-
suspicion framework, we are not constrained by that legal analysis because, as an appellate
court, we “independently review de novo the issue of probable cause.” State v. Lee, 585
N.W.2d 378, 383 (Minn. 1998). The state may defend the underlying decision on an
alternative ground “when there are sufficient facts in the record for the appellate court to
consider the alternative theories, there is legal support for the arguments, and the alternative
grounds would not expand the relief previously granted.” State v. Grunig, 660 N.W.2d 134,
137 (Minn. 2003). In conducting our review, appellate courts “review the district court’s
findings of . . . fact relating to the probable cause determination for clear error under the
clearly erroneous standard,” giving “due weight to inferences drawn from those facts by
resident judges.” Id. (quoting Ornelas v. United States, 517 U.S. 690, 699 (1996)).
With that framing in mind, we first consider whether the officers had probable cause
at the time of the initial stop and arrest. We then reach Middlebrook’s ineffective-
assistance-of-counsel argument.
I
The Fourth Amendment to the United States Constitution and article I, section 10
of the Minnesota Constitution guarantee the “right of the people to be secure in their
persons, houses, papers, and effects” from “unreasonable searches and seizures.” U.S.
Const. amend. IV; Minn. Const. art. I, § 10. For a warrantless arrest to be valid under those
provisions, the arrest must be supported by probable cause. State v. Harris, 121 N.W.2d
8
327, 330-31 (Minn. 1963). Courts “apply an objective standard for determining the
lawfulness of an arrest or a search by taking into account the totality of the circumstances
to determine whether the police have probable cause to believe that a crime has been
committed.” State v. Hawkins, 622 N.W.2d 576, 579-80 (Minn. App. 2001). That inquiry
involves a determination of “whether the objective facts are such that under the
circumstances a person of ordinary care and prudence would entertain an honest and strong
suspicion that a crime has been committed.” State v. Johnson, 314 N.W.2d 229, 230 (Minn.
1982) (quotation omitted).
We begin by reviewing the facts known to the officers at the time of Middlebrook’s
arrest. The district court found: (1) Middlebrook “and his vehicle were known to the
officers based on prior narcotic investigations,” (2) Middlebrook “was parked in what the
officers considered or testified to be an open drug area,” (3) Middlebrook remained parked
there for “approximately an hour and a half,” and (4) Middlebrook “was observed engaging
in a hand-to-hand transaction with an unknown male who walked a short distance away
and began to visibly smoke narcotics with other known individuals immediately after
engaging in what officers believed to be a hand-to-hand transaction with” Middlebrook.
5

5 The district court made several additional findings regarding other individuals who
interacted with Middlebrook during the observation period. Middlebrook argues on appeal
that the district court’s findings regarding other transactions are clearly erroneous. Though
the Milestone footage in the record shows other individuals interacting with Middlebrook,
we need not reach Middlebrook’s argument about the district court’s findings in this regard
because we conclude that, even excluding those findings, the evidence is sufficient to
establish probable cause.
9
Middlebrook argues that those facts do not support probable cause because the
officers also admitted that they could not see the hand-to-hand transaction as it was
obscured by the dash board, and they could not definitively say that the Middlebrook
supplied the narcotics that the individual then smoked with the group. But probable cause
does not require such definitiveness. When assessing whether probable cause existed, “the
totality of the circumstances includes reasonable inferences that police officers draw from
facts, based on their training and experience, because police officers may interpret
circumstances differently than untrained persons.” State v. Lester, 874 N.W.2d 768, 771
(Minn. 2016). Courts may then consider those reasonable inferences when making a
probable-cause determination. Id. Here, the district court found Officer D. credible,
including the inference Officer D. drew that a hand-to-hand transaction took place. On
appeal, we are required to “give due weight to reasonable inferences drawn by police
officers and to a district court’s finding that the officer was credible and the inference was
reasonable.” Id. at 771 (quotation omitted). Therefore, even if the officers did not see an
actual exchange of narcotics because of the dashboard, we accept the district court’s
credibility finding and the officers’ inference that a hand-to-hand transaction took place.
Middlebrook also argues that, even accepting the officers’ inference that a hand-to-
hand transaction occurred, one such exchange is insufficient to support probable cause to
arrest. But the totality of the circumstances here includes more than just one exchange. Our
caselaw provides a helpful comparison on this point. In Hawkins, this court concluded that
police had probable cause to arrest Hawkins based on the following facts:
10
The officers watched Hawkins for about 15 minutes riding a
bicycle around an intersection. Hawkins whistled and waved at
approaching vehicles, which [Officer] Willis testified is a
common way for street -level narcotics dealers to get people’s
attention and let them know that they are selling narcotics.
Hawkins also conducted two hand-to- hand transactions with
other individuals in a manner that Willis concluded was
consistent with a drug transaction and not with innocent
behavior.

622 N.W.2d at 581. The facts supporting probable cause here are at least as compelling as
those in Hawkins. The officers observed what they believed, based on their training and
experience, to be a hand-to-hand transaction; the officers knew Middlebrook from previous
narcotics cases; the transaction occurred in a known open-air drug market; and officers saw
the other party to the transaction almost immediately use suspected narcotics.
Middlebrook maintains that there may be innocent explanations for the behavior
observed by the police. But this court rejected a similar argument in Hawkins, underscoring
that officers may draw conclusions based on their expertise and experience, even when
there might be an innocent explanation for the observed conduct. Id. at 580.
Considering the surrounding circumstances in their entirety, we conclude that the
facts here would “permit a prudent person to reasonably believe” that Middlebrook “had
engaged in the sale of drugs.” Id. at 581. Thus, the officers had probable cause to arrest
Middlebrook when they arrived on scene and their subsequent searches of Middlebrook’s
person were lawful. State v. Bernard, 859 N.W.2d 762, 767 (Minn. 2015) (noting that,
under the search-incident-to-lawful-arrest exception to the warrant requirement, “the police
are authorized to conduct a full search of the person who has been lawfully arrested”
11
(quotation omitted)), aff’d sub nom. Birchfield v. North Dakota, 579 U.S. 438 (2016). We
therefore affirm the district court’s denial of Middlebrook’s motion to suppress.
II
Middlebrook also argues that his trial counsel was ineffective for not challenging
the warrantless search of his vehicle. The state argues that Middlebrook’s trial attorney did
not engage in objectively unreasonable conduct in focusing his strategy on the “general
probable cause determination” rather than separately challenging the search of the car, and
that, regardless, Middlebrook cannot show prejudice because the argument was meritless.
We agree with the state that Middlebrook has not established prejudice.
To succeed on an ineffective-assistance-of-counsel claim, one must prove both that
counsel’s conduct was objectively unreasonable and that there is a reasonable probability
that, but for counsel’s unreasonable conduct, the outcome would have been different.
Strickland v. Washington, 466 U.S. 668, 687, 694 (1984); State v. Rhodes, 657 N.W.2d
823, 842 (Minn. 2003). The Minnesota Supreme Court has held that whether someone was
prejudiced by counsel’s failure to move to suppress specific evidence depends on whether
the district court “would have granted a motion to suppress the . . . evidence if one had
been made.” Johnson v. State, 673 N.W.2d 144, 148 (Minn. 2004).
Here, even assuming that the actions of Middlebrook’s trial counsel were
objectively unreasonable, we conclude that his ineffective-as sistance claim must fail
because Middlebrook has not established that such conduct resulted in prejudice. See
Andersen v. State, 830 N.W.2d 1, 10 (Minn. 2013) (“We need not address both the
performance and prejudice prongs if one is dispositive.”). Even if trial counsel here had
12
separately challenged the warrantless search of the vehicle in the motion to suppress, it
likely would have failed in light of our conclusion that the officers had probable cause to
arrest Middlebrook and search his person. Having established probable cause at the time
of arrest, any number of exceptions to the warrant requirement may have applied to a search
of the vehicle, making it lawful. See, e.g., Arizona v. Gant, 556 U.S. 332, 351 (2009)
(search of vehicle incident to lawful-arrest exception); Lester, 874 N.W.2d at 771
(automobile exception); State v. DeWald , 463 N.W.2d 741, 748 (Minn. 1990)
(instrumentality-of-a-crime exception related to vehicles). Accordingly, Middlebrook is
not entitled to relief based on ineffective assistance of counsel.
Affirmed.