Style Lessons from Syed v. State: Eight Ways to Make a Good Brief Great

On my mark-up of the State’s brief, I have a lot to say about how the State handled the facts, the case law, and the overall organization of its argument. Here, I extract eight sets of ready-for-action style tips that you can use today.

First, aim high, but only high enough.

Syed does not suggest, nor could he, that Gutierrez’s representation was a complete failure, and, indeed, the record establishes the opposite.

“The opposite” would be a “complete success.” But he was convicted and sent to prison!

Second, tell a story that’s both believable and easy to follow.

1. Use words that the parties themselves might have used.

Wilds—who pled guilty to being an accessory to the murder and agreed to take the stand for the State—testified that Syed left him his cell phone and car, instructing him to be ready to retrieve Syed when he called.

“telling him to be ready to pick Syed up”

Wilds testified that, afterwards, Syed convinced him to help dispose of the body.

“Syed later”

On a newly-acquired cell phone, which was activated a day before the murder, Syed called Wilds to determine if he was available the next day.

“find out” (also cut the hyphen in “newly-acquired”)

Syed also elected not to attend the memorial service for Lee, telling Inez Hendricks, another teacher at Woodlawn, that he skipped the service because he and Lee practiced different religions.


2. Use the past perfect to help clarify chronology.[1]

At the hearing, Chaudry stated that she spoke to Syed on multiple occasions by phone from the time of his arrest and throughout both trials; she attended most of the second trial and participated in two meetings between Gutierrez and Syed’s parents.

“had spoken”

Griffin’s attorney expected his client to take a plea and therefore admitted that he did not contact any potential alibi witnesses in preparation for trial.

“had not contacted”

Syed also introduced an affidavit McClain[] signed a year later, on March 25, 2000.

“that McClain had signed” (otherwise it sounds like McClain signed the affidavit AFTER Syed introduced it)

Syed presented evidence to the post-conviction court that he made his defense team aware of these two original letters.

“had made”

The court also correctly determined that Syed did not establish a failure to perform by Gutierrez with respect to investigating Asia McClain.

“had not established”

The post-conviction court also rejected Syed’s contention that Gutierrez was constitutionally deficient for failing to seek a plea offer that Syed claimed he[] requested.

“had requested”

Third, punctuate precisely and accurately.[2]

1. Add a comma before a nonrestrictive “who” (the State makes this mistake throughout the brief).

Urick’s characterization of McClain’s reticence is confirmed by Syed’s present counsel[,] who said that although he tried to produce McClain, she evaded service of the defense subpoena.

After school ended, Wilds received a call from Syed[,] who directed him to the Best Buy store on Security Boulevard.

At the second trial, as set forth in greater detail below, the State’s case included, inter alia, the testimony of Wilds[,] who helped Syed bury the victim and later led police to the victim’s car.

So he joined Syed[,] who had secured two shovels and returned to the Park & Ride to retrieve Lee’s car.

2. Insert commas after introductory phrases.

Syed reported that during the struggle[,] Lee had kicked off the car’s turn signal and had attempted to apologize to him.

Wilds testified that over the next few hours[,] he and Syed alternated between driving around in search of marijuana, attempting to establish an alibi for Syed, and disposing of the body.

3. Insert commas before independent clauses.

The Supreme Court has never recognized a defendant’s right to a plea[,] and the jurisprudence concerning plea negotiations manifestly does not support Syed’s claim to ineffective counsel on this basis.

4. Insert commas before participles that modify the preceding phrases and not just the last word.

Although police originally considered other suspects, particularly Alonzo Sellers (the person who came across the body in Leakin Park), the evidence uniformly converged on Syed[] beginning with the tip provided by the anonymous caller.

5. Insert commas around a midsentence “however.”

She notes[,] however[,] that she aspires to become a criminal psychologist for the FBI.

6. Avoid putting a comma after the word “that” when it introduces a quotation.

According to Chaudry, Syed told her that, [cut] “it was like any other day for me,” and that he had no specific memory of speaking to McClain (or anyone else at the library) that day.

(Cut the comma after “me” as well, because Syed told Chaudry two things, not three or more.)

7. Avoid putting a comma before “so that.”

Pusateri added that they later returned to Westview Mall, [cut]so that Wilds could make sure there were no prints on the shovels they had left behind.

8. Avoid putting commas in compound predicates (watch Mary Norris’s new video).

In Lafler v. Cooper, 132 S. Ct. 1376 (2012), and Missouri v. Frye, 132 S. Ct. 1399 (2012), the Court recognized a right to effective counsel in the context of plea bargaining, [cut] but did not contemplate creating a duty to seek a plea when none has been offered.

(Or better yet, add “it” after “but.”)

9. Avoid putting a comma in a series of adjectives that modify each other.

The only evidence supporting this claim is Syed’s own, [cut] self-serving post-conviction testimony, which the post-conviction court did not credit.

(Hint: If you couldn’t insert “and” between two adjectives, don’t use a comma.)

10. Avoid putting commas before a quotation unless it follows a word of speech like “said.”

He told Wilds that killing Lee “kind of hurt him,” but that when someone treated him the way she had, that person deserved to die; Syed later added that the murder, [cut] “kind of makes [me] feel better and then again it doesn’t.”

11. Avoid using a dash to splice together two independent clauses.

The post-conviction testimony of Syed’s mother is perhaps the best evidence of this clearly Gutierrez was hired and paid substantial sums to obtain an acquittal, not a guilty plea.

(A colon might work better here. And cut the word “clearly.”)

Fourth, watch verb agreement.

The testimony of witnesses familiar with Syed, Lee, and the events of January 13 were one component of the State’s case.

Should be “was” to agree with “testimony,” not “witnesses.”

After all, the law clerk’s notes upon which Syed relied to show that the defense was aware of the McClain letters in the first place also reveal that, on the same date the McClain correspondence was discussed, the defense team obtained — presumably from Syed — his email account information and were made aware that the public library may have had surveillance cameras.

Team is a collective noun that takes “was,” not “were.”

Neither Simms nor Williams state that the alibi notice was not admissible for this purpose. Syed actually relied on the notice in his closing argument to the post-conviction court.

With “neither . . . nor,” agree with the second noun. So “states,” not “state.”

Fifth, use parallel structure for parallel ideas.

1. Use parallel structure in lists.

Gutierrez also pursued an alibi defense at trial, through subtle cross-examination of witnesses presented by the State, by substantiating a reliable routine that Syed followed every day, i.e., attendance at school followed by track practice followed by services at the mosque, and by calling to testify for a specific alibi Syed’s father, a credible and sympathetic figure who asserted that on the evening of Lee’s disappearance he went to the mosque with his son at approximately 7:30 p.m. for an 8 p.m. prayer meeting.

Delete the comma and change “through subtle cross-examination of witnesses presented by the State” to “by subtly cross-examining the State’s witnesses.”

While driving, Syed told Wilds about how hurt he was by Lee’s treatment of him, how mad she made him, and said to Wilds, “I’m going to kill that bitch.”

The list needs parallel structure: “Syed told Wilds about X and Y and then said Z.”

Syed’s mother testified that Gutierrez was hired because “she had a reputation for being very tough,” []an “extensive background in trying criminal cases,” and was known for “fighting very hard for the client.”

Insert “had” here for parallel structure in the list.

But not only did Syed eventually disavow any plans to get a ride after school from Lee; he also shifted from telling Officer O’Shea, on the one hand, that he went to track practice after last seeing Lee during the final class period of the day to, on the other hand, feigning that he had no memory at all of the day his ex-girlfriend vanished when asked by the lead homicide detective a month later.

Move “on the one hand” to after “from” to create proper parallel structure with the “from . . . to” correlative-conjunction construction.

2. Carry “that” throughout your lists.

Moreover, Syed claimed that Gutierrez advised him that she had explored the McClain alibi and nothing had come of it.

The second “that” is missing. Change to “but that.”

Syed also introduced an affidavit McClain signed a year later, on March 25, 2000, in which McClain claimed she saw Syed at a specific time at the library on the day of Lee’s murder, and that she was never contacted by Syed’s defense team.

Insert “that” after “claimed” so that it matches “that she was never contacted” in the next part of the sentence.

He argues that, upon his purported request to seek a plea offer, Gutierrez was constitutionally obligated to engage the prosecution in plea negotiations, and[] her failure to do so cost him the opportunity to choose between pleading guilty and going to trial.

The second “that” is missing.

3. Repeat prepositions as needed for clarity.

Around that time, Syed received phone calls from the victim’s brother, Young Lee, and[] Officer Adcock, asking if Syed knew where his ex-girlfriend was.

Repeat “from” here to avoid misreading as a series.

Sixth, lighten, shorten, and punch up your prose.

1. Change verb-adverb combinations to stronger verbs.

The week of the murder, as Lee’s affection for Syed visibly flickered, her relationship with Cliendinst at once became sexually intimate and public at school.

It’s awkward to pair the adverb “visibly” with the “flickered” metaphor. Perhaps “as Lee stopped showing affection toward Syed.”

After one of the calls, Syed abruptly motioned to Wilds that it was time to leave.

“Syed gestured to Wilds”

Although police originally considered other suspects, particularly Alonzo Sellers (the person who came across the body in Leakin Park), the evidence uniformly converged on Syed beginning with the tip provided by the anonymous caller.

“all the evidence led to Syed”

Both letters express hope that Syed is innocent and simultaneously relay concerns that he is not: “I want you to look into my eyes and tell me of your innocence.”

“while relaying”

Put simply, Gutierrez’s team assiduously developed 80 alibi witnesses that would conform to the account provided by Syed to police.

“managed to find”

That day at Woodlawn, Syed lured Lee away from the high school campus, falsely claiming he needed a ride to pick up his car.

“pretending that he needed”

2. Cut “of” phrases.

. . . tensions that inexorably arise in the course of a trial.

Change to “during.”

3. Avoid using “where” legalistically.

Syed also failed to establish that the State, charged with prosecuting the ruthless murder of a young girl where the State possessed overwhelming evidence, would have contemplated offering Syed any plea at all.

“Where” doesn’t work here, and it almost suggests that the State is about to tell us “where” the ruthless murder took place. Try “in the face of overwhelming evidence.”

Where Gutierrez, a diligent and experienced trial attorney, developed an alibi theory based on Syed’s usual routine, a court should not revisit an attorney’s judgment to adhere to one alibi theory instead of pursuing another.

Start with “Because,” change “a court” to “the Court,” and change “an attorney’s” to “her” (the State is trying to link a specific point about Gutierrez with a general legal point, and it just doesn’t work).

And where a seasoned defense attorney like Gutierrez generates a list of 80 potential alibi witnesses, it is reasonable to conclude that some inspection of this 81st alibi witness was performed.


4. Avoid Latin unless it’s a term of art.

This time, contradicting what Syed had told Myers (i.e., that Lee was going to give him a ride to pick up his car) and what he told Officer Adcock (i.e., that Lee was supposed to give him a ride home), Syed stated that he would not have needed a ride from Lee since he had his own car.

Cut i.e. in both places―it’s superfluous. Better yet, set off the contrasting accounts with dashes.

In fact, as discussed, supra, the Supreme Court held in Lafler, 132 S. Ct. 1376, and Frye, 132 S. Ct. 1399, that the Strickland standard applies to claims of ineffective assistance of counsel with respect to plea negotiations.

No comma before supra, but in any event, just write “above.”

5. Avoid common wordy phrases: “there is,” “there are.”

By failing to produce McClain at the post-conviction hearing, there was no showing that her testimony would have been helpful to the defense. Thus, Syed failed, as a matter of law, to prove that any failure by Gutierrez to investigate or call McClain as a witness prejudiced his right to a fair trial.

“By failing to produce McClain at the hearing, Syed appears to have conceded that her testimony would not have helped the defense.”

For Syed and Wilds, there were points during the burial at Leakin Park where both men seemed disturbed and disoriented by the gravity of the moment.

“At different points during the burial, both Syed and Wilds seemed disturbed and disoriented by the gravity of the moment.”

Furthermore, Syed’s claim is dependent on there being credible evidence that he asked Gutierrez to seek a plea offer from the State, that she failed to do so, and that she lied to him when she stated she did.

Scrap “there being” and replace with something like “Syed’s claim requires credible evidence.”

6. Avoid common wordy phrases: “with respect to.”

She corroborated, for instance, Wilds’ testimony with respect to the afternoon, stating that Wilds had been at her home playing video games, waiting for a phone call.

Change to “about.”

The court also correctly determined that Syed did not establish a failure to perform by Gutierrez with respect to investigating Asia McClain.

Perhaps “Syed had not established that Gutierrez failed to perform when she declined to investigate Asia McClain.”

7. Avoid common wordy phrases: “at the time when.”

At the time when Syed retained her, however, she was a renowned criminal defense attorney who was hired because Syed and his family wanted to obtain an outright acquittal.

Cut to just “When.”

8. Avoid common wordy phrases: “upon which.”

Gutierrez clearly had a basis upon which to conclude that McClain’s information was either false, unreliable, immaterial, or harmful to the defense.

9. Avoid common wordy phrases: “assuming arguendo.”

Even assuming arguendo that Syed met his burden of production with respect to the first prong of Strickland, his claim would still fail.

Change to “if.”

Even assuming Syed raised a cognizable ineffective assistance of counsel claim, he still failed to establish that Gutierrez acted deficiently in the context of his case.

Change to “if Syed had.”

Even assuming arguendo that McClain’s offer of an alibi warranted some attention, Syed bears the burden of proving that Gutierrez failed to do so.

Change to “if.”

10. Avoid common wordy phrases: “have an opportunity to.”

In fact, Gutierrez, aware that Maryland rules required her to disclose potential alibi witnesses in advance of trial so that the State would have an opportunity to investigate the basis of the alibi, provided to the State a list of 80 potential alibi witnesses on October 5, 1999.

Cut to “could.”

11. Avoid common wordy phrases: “so-and-so states” before a quotation.

Indeed, at the bottom of the second page of the March 1, 1999, letter, McClain openly qualifies her information when she states: “If you were in the library for awhile, tell the police and I’ll continue to tell what I know even louder than I am.”

Cut this phrase and put the colon after “information.”

12. Avoid common wordy phrases: “the manner in which.”

This finding is not only consistent with the manner in which the case was defended, but also by Syed’s own words.

Change to “how.”

13. Avoid redundancies.

In light of these facts, any attempt by trial counsel to engage the prosecution in plea negotiations certainly would have been a futile, if not counterproductive, effort.

These “double trouble” constructions are often more trouble than they’re worth. “Effort” here is superfluous, for example, and the State could have simply written that the attempt “would have been futile, if not counterproductive.”

Seventh, transition effectively.

1. Favor light connectors over heavy ones.

Furthermore, there is also no proof that Syed would have entertained a plea offer that required him to serve time in prison.

“Nor is there proof . . .”

In fact, there is no evidence in the record—at trial or in the post-conviction proceedings—that visiting the library to check email between school and track practice was part of Syed’s habitual pattern; accordingly, it would have been a conspicuous aberration from the daily routine that Gutierrez sought to establish.

When you have two complex sentences, the last thing you want to do is to join them with a semicolon and “accordingly.” Start a new sentence here instead: “A library visit would have thus been a conspicuous departure from . . .”

2. Avoid meaningless transitions.

Furthermore, whereas “[a] reasonable probability is a probability sufficient to undermine confidence in the outcome,” id. at 694, “[i]t is not enough for the defendant to show that the errors had some conceivable effect on the outcome of the proceeding,” id. at 693.

“Furthermore” adds nothing when it just means “now I’m going to say something else.” Start with “Whereas.” Or, better yet, “Although.”

Eighth, streamline your syntax.

1. Put like words and phrases together.

In addition, because Syed did not produce McClain at the post-conviction hearing, Syed failed, both as a matter of law and on the facts of this case, to establish prejudice.

Splitting “to establish prejudice” from “Syed failed” makes the sentence confusing. Move it back to where it belongs.

The week of the murder, as Lee’s affection for Syed visibly flickered, her relationship with Cliendinst at once became sexually intimate and public at school.

Other way around: “became at once sexually intimate and public.”

By failing to produce McClain at the post-conviction hearing, there was no showing that her testimony would have been helpful to the defense. Thus, Syed failed, as a matter of law, to prove that any failure by Gutierrez to investigate or call McClain as a witness prejudiced his right to a fair trial.

“Syed thus failed to prove . . .”

To support these claims, defense counsel called to testify five witnesses at the post-conviction hearing: Kevin Urick (one of the original prosecutors who tried the case), Rabia Chaudry (Syed’s close friend), Shamin Rahman (Syed’s mother), Margaret Meade (admitted as an expert in criminal defense in Baltimore City), and Syed himself.

“called five witnesses to testify”

When police executed a search warrant at Syed’s residence, they found a November 1998 letter from Lee tucked into a textbook, in which Lee sought to reassure Syed that they would both survive a breakup: “Your life is NOT going to end.”

The “in which” appears to be modifying the textbook, which makes no sense. (Plus you don’t need a comma, because it’s restrictive.) Try “they found tucked into a textbook a November 1998 letter in which Lee sought.”

Syed failed to establish that Gutierrez’s strategy and judgment with respect to an alibi defense based upon Asia McClaine was constitutionally deficient.

The verb-agreement error here (“was” should be “were”) is also a good example of why it’s better to keep like parts of a sentence together.

To corroborate this, he referred to the notes of one of Gutierrez’s law clerks, which suggest that McClain was discussed at a meeting between Syed and the clerk.

Avoid “notes of one of” and clarify that “which suggest” modifies “the notes.” Perhaps “he referred to the notes taken by one of Gutierrez’s law clerks, which suggest.”

2. Place “only” carefully.

It should also be noted that, if Syed only desired a 20- or 30-year plea offer, imposing a constitutional requirement that his counsel be the first to act in the context of what can be subtle, delicate bargaining is a mistake.

“desired only”

To the contrary, the post-conviction court, which observed Syed’s testimony, found as fact that, at the time of trial, Syed was only interested in pursuing a full acquittal.

“interested only”

3. Include the word “that” to avoid miscues.

Second, Syed claimed [that] he asked Gutierrez to approach the State about a plea deal and [that] she failed to do so.

Wilds estimated [that] it was around 7 p.m.; a little earlier, Wilds had used Syed’s cell phone to page a friend of his, Jennifer Pusateri, to alert her that they would not be meeting up as they had previously planned.

(Otherwise it sounds like “it” is the object of “estimated.”)

4. Favor the active voice even within phrases.

This argument fails in any event. None of the cases cited by Syed support the argument that defense counsel is ineffective per se by not engaging the prosecution in plea negotiations.

“Syed cites”

Even if Syed relies upon McClain’s affidavit (which states that she was not contacted by a member of Guterriez’s team), speaking to McClain is not the only way for Gutierrez to have assessed the value and veracity of the potential alibi.

“that no one on Gutierrez’s team contacted her”

Put simply, Gutierrez’s team assiduously developed 80 alibi witnesses that would conform to the account provided by Syed to police.

“Syed provided”

The only evidence before the post-conviction court that Syed ever asked Gutierrez to seek a plea deal was Syed’s testimony, which was not credited by the court.

“the court did not credit”

5. Avoid using “this” ambiguously.

This indicates that McClain may have been guessing about Syed’s presence in the library, or that her recollection was mistaken if not fabricated.

“This” is ambiguous. This statement? This promise?

Indeed, this must be the case because, in the absence of formalized plea terms, it is difficult to fashion an appropriate remedy for the purported constitutional violation.

“This” is used to refer vaguely to some previous point.

What remains is a dubious affidavit prepared long ago by McClain that, according to Urick’s testimony, was generated as a result of pressure from Syed’s family in the wake of Syed’s conviction at trial. The court below rightly found that this was insufficient to meet Syed’s burden.

“This” is ambiguous. Change to “this solicited affidavit.”

6. Place “however” carefully.

The post-conviction court, however, did not credit even the first of these assumptions.

Move “however” to the end of the sentence. It’s not the court that’s being contrasted here, but the court’s findings with Syed’s burden.

7. Use the proper form with common verb constructions.

Pusateri also encouraged police, at Wilds’ suggestion, that they should talk with Wilds.

You don’t “encourage” someone that they “do” something. You encourage the police “to” talk to Wilds.

After Syed’s arrest, McClain sent Syed two letters, dated March 1, 1999, and March 2, 1999, requesting to talk with him to explore the relevance of a conversation McClain recalls having on January 13, 1999, at the nearby public library.

“Requesting” does not take an infinitive. “Asking to talk with him.”

8. Be careful with the “not only . . . but” construction.

Not only did Syed decline to participate in these efforts, [but] he affirmatively sought to thwart them, especially once he learned that he was a subject of interest.

Not only was there no credible evidence before the post-conviction court that Syed asked Gutierrez to seek a plea offer, [but] there was no credible evidence that Gutierrez lied to Syed in the manner he alleges.

This finding is not only consistent with how the case was defended, but also by Syed’s own words.

This last sentence has a classic “not only . . . but (also)” parallelism glitch, and “by” doesn’t work with “consistent” (something isn’t “consistent by” something). “The finding is consistent NOT ONLY with how the case was defended BUT ALSO with Syed’s own words.”

[1] In a complex story, when many sentences include several events all in the past, it is essential to distinguish between the simple past and the past perfect.

[2] Punctuation, particularly comma usage, is an issue throughout the brief. See my article Eight Comma Commandments.