Vanessa Rawlins, Plaintiff, v. UBER TECHNOLOGIES INC (2026)

Background

This matter arises out of a motor vehicle collision that occurred on February 9, 2019. In the complaint, Plaintiff alleged that the accident occurred on Belmont Avenue at or near its intersection with Hinsdale Street in Kings County (Brooklyn), New York. Plaintiff claimed she was a passenger in a vehicle operated by her husband Anderson Newlin Rawlins which was struck by a vehicle owned and operated by Defendant Soe Myint, who was logged in to the ride-sharing app of Defendant Uber Technologies, Inc. The latter denied the allegations of the complaint, specifically allegations pertaining to Uber's being vicariously liable for Defendant Soe Myint's negligence.

On November 7, 2022, an order was issued granting Plaintiff summary judgment on liability with respect to Defendant Soe Myint, i.e., he was held liable for the occurrence of the subject accident. The matter was assigned to this Court for trial. and the court conducted a liability trial on June 8, 16, and 17, 2026 concerning whether Uber Technologies, Inc. was vicariously liable for defendant Myint's negligence, which depended on whether he was an employee or independent contractor of Uber Technologies, Inc.

Plaintiff called as a witness Benjamen Carroll, who worked as a senior manager of corporate business operations on the U.S. and Canada city operations team at Uber Technologies, Inc. around the time of the subject motor vehicle accident. Now he worked on the global intelligence operations team.

Because Uber Technologies, Inc. was a defendant in this case, Mr. Carroll was an employee of an adverse party to Plaintiff. During direct examination, he was cagey in responding to Plaintiff's questions. Therefore, the Court permitted Plaintiff's counsel to ask Mr. Carroll leading questions. However, when defense counsel from Uber Technologies, Inc. questioned Mr. Carroll on cross-examination, the latter was forthright and open. When said defense counsel asked leading questions of Mr. Carroll during his cross-examination, Plaintiff's counsel objected. The Court sustained these objections, precluding said defense counsel from asking leading questions of his client's employee. Said defense counsel disputed these determinations of the Court, an example being:

Q. Uber sells drivers leads, right?

A. Yes.

Q. And also customer service support.

A. Yes.

Q. That's part of the --

MR. HUTNNER: Judge, I'm just going to object. I was leaving it alone but it's starting to get to me, all the leading.

MR. BERBENICH: It's cross examination, your Honor.

THE COURT: He's your witness; so I'm going to sustain. Go ahead. We'll take it on a question-by-question basis if it becomes an issue. Sustained. Go ahead. (Tr at 275, lines 8-22 [June 17, 2026].)

Discussion

A leading question is one which suggests the desired answer within the question (see People v Mather, 4 Wend 229, 247 [Sup Ct Judicature 1830]). Leading questions are subjective, and the propriety of asking them is to be determined in the court's discretion based on the content, form, or tone of the question (Robert A. Barker & Vincent C. Alexander, 5 NY Prac, Evidence in New York State and Federal Courts § 6:70 [2023]).

The Guide to New York Evidence rule 6.06 (Scope and Manner of Examination of Witnesses) provides the rule for leading questions on direct examination within subdivision (4): "(b) When a party calls (i) an adverse party, (ii) a witness identified with an adverse party, or (iii) a witness who is hostile or becomes hostile during examination, the court may permit leading questions in conducting the direct examination" (https://www.nycourts.gov/JUDGES/evidence/6-WITNESSES/6.06.%20Scope_&_Manner _of_Examination_of_Witnesses.pdf [last accessed June 18, 2026]).

Pursuant to this rule, Plaintiff was permitted to ask Mr. Carroll leading questions on direct examination because he was identified with an adverse party — he was an employee of Defendant Uber Technologies, Inc. In addition, Mr. Carroll was hostile during his examination. Often, he answered "no" to Plaintiff's questions or attempted to avoid answering them directly. He even stated that he did not remember prior deposition testimony about which Plaintiff questioned him.

Examples of the leading questions to which the Court sustained Plaintiff's objections are as follows:

• "Maximum hours -- that's set by the TLC in 2019?" (tr at 280, line 13 [June 17, 2026]).

• "The Technology Services Agreement -- for that to apply to Mr. Soe, you would agree with me, he would have to choose to use a smartphone, a smart device --" (id. at 283, line 22-24).

• "Uber Technologies sells Mr. Soe leads, true?" (id. at 285, line 14).

With respect to leading questions on cross-examination, the Court looked to Matter of Sheltering Arms Children's Servs. v Yiweiz (246 AD3d 677 [1st Dept 2026]). There, the petitioner called the respondent's client as a witness. During cross-examination, the respondent was not permitted to ask leading questions because there was no reason to believe that the respondent's client would be evasive, nonresponsive, or hostile toward her own counsel, even though she was technically being cross-examined.

Applying Sheltering Arms to this case, the Court notes that Mr. Carroll was not evasive, nonresponsive, or hostile toward defense counsel. Moreover, although Plaintiff called Mr. Carroll as a witness, Mr. Carroll is an employee of Defendant Uber Technologies, Inc. New York law does not give attorneys an automatic right to ask leading questions on cross-examination where the witness has not demonstrated evasiveness, hostility, or similar difficulty. Rather, the purpose of permitting leading questions is to allow counsel to control a difficult witness, which was not the case here. Therefore, the Court sustained the objections of Plaintiff to defendant Uber Technologies Inc.'s counsel's leading questions on cross-examination.

Conclusion

Accordingly, the Court ruled that Plaintiff was not precluded from asking Benjamin Carroll, Uber Technologies, Inc.'s employee, leading questions during direct examination, and that Defendant Uber Technologies, Inc. was precluded from asking leading questions of him during cross-examination.

HON. AARON D. MASLOW

Justice of the Supreme Court of theState of New York

Aaron D. Maslow, J.