In this fraud and breach-of-contract action, plaintiff, ELRAC LLC, d/b/a Enterprise Rent-a-Car, and defendant, Steven Feldman, both move to strike the other’s pleadings for asserted failures to comply with discovery obligations, including obligations imposed by orders of this court. The two motions (motion sequences 005 and 006) are consolidated here for disposition. This is the third motion in this case seeking to strike defendant’s pleadings for failure to provide discovery. This court twice previously required defendant to cover plaintiff’s attorney fees and to comply with discovery obligations going forward in order to avoid having his pleadings stricken. This court now concludes that striking defendant’s answer is the only appropriate sanction for defendant’s continued failure to respond meaningfully to plaintiff’s discovery requests. Plaintiff’s motion to strike (motion sequence 006) is granted. Defendant’s motion (motion sequence 005) is denied as academic. BACKGROUND According to the allegations of the complaint, defendant owned a parcel of land in Brooklyn that plaintiff wished to lease and turn into a car-rental facility. That use for the property would have required a zoning variance. Plaintiff alleges that defendant repeatedly promised plaintiff that he would lease it the property and help it obtain the necessary variance from the City Board of Standards and Appeals (BSA) — and that in reliance on these promises, plaintiff spent substantial time and money over a two-year period preparing site plans and the other materials needed to secure a variance and move forward with converting the property to plaintiff’s preferred use. Plaintiff further alleges that after expending these resources, it became aware that defendant had gone behind its back and instead marketed and sold the property to a residential developer. In the fall of 2015, plaintiff brought this action, asserting claims for breach of contract, promissory estoppel, and fraud. In November 2016, the parties appeared before this court for a preliminary conference to set a discovery schedule. The schedule envisioned among other things that the parties would serve document productions on each other in early 2017, with depositions to be held promptly thereafter. (See NYSCEF No. 10.) Plaintiff served document demands on defendant in early February 2017. Defendant did not respond. At the end of April 2017, the parties appeared before this court for a compliance conference, at which defendant was ordered to provide document responses within 30 days, with a follow-up status conference scheduled for November 1. (See NYSCEF No. 11.) Defendant did not comply. In October 2017, having received no documents or any response to a good-faith letter, plaintiff moved to strike, with the motion returnable for October 30. (See NYSCEF Nos. 12-18.) Defendant did not file any papers in response. The parties then came before this court for the scheduled status conference on November 1. The court adjourned the motion to late January 2018 to afford defendant additional time to serve document responses or oppose the motion to strike. Defendant did neither. This court therefore granted the motion to strike as unopposed. (See NYSCEF No. 19.) In March 2018, defendant moved to vacate this court’s January 2018 order striking his answer, pleading law office failure. (See NYSCEF No. 26.) In August 2018, after hearing oral argument on the motion to vacate, this court granted the motion, but only on condition that (i) defendant pay plaintiff $2500 in partial payment of attorney fees incurred by plaintiff on the motion to vacate and prior court appearances; and (ii) provide all outstanding discovery within 30 days. (See NYSCEF No. 44.) On August 31, 2018, defendant responded to plaintiff’s February 2017 document demands, as required by this court’s order. Defendant did not, however, produce any documents. Instead, his response asserted a limited number of boilerplate objections and otherwise denied being in possession of any responsive documents. (See NYSCEF No. 46.) In October 2018, plaintiff again moved to strike, contending that defendant’s August 31 document response flouted the condition in this court’s August 2018 order that he comply with all outstanding discovery obligations. (See NYSCEF Nos. 48-58.) Defendant did not file any papers in response to this motion. In November 2018, therefore, this court again granted plaintiff’s motion to strike as unopposed. (See NYSCEF No. 59.) At the end of November 2018, defendant again moved to vacate. (See NYSCEF Nos. 64-95.) In January 2019, after hearing oral argument on the second motion to vacate, this court reluctantly granted the motion. But this court conditioned vacatur on defendant (i) paying plaintiff more than $9,000 in attorney fees, (ii) responding to all discovery demands, and (iii) not violating any future court orders. (NYSCEF No. 114.) In April 2019, defendant produced approximately 300 pages of documents in response to plaintiff’s initial discovery requests — more than two years after plaintiff first served those requests. (See NYSCEF No. 117.) In late May 2019, defendant also served supplemental document requests on plaintiff. Plaintiff did not respond to those requests. In July 2019, the parties came before this court for a status conference. At the conference, the parties stipulated that plaintiff would serve supplemental document demands on defendant, who would have time to respond or object to those demands. This court so-ordered that stipulation. (See NYSCEF No. 127.) In late August 2019 defendant responded to plaintiff’s supplemental demands. Defendant did not, however, produce any new documents. Instead, he asserted the identical objection to each document demand. (See NYSCEF No. 122.) In September 2019, defendant moved to strike plaintiff’s pleadings as a discovery sanction under CPLR 3126 for failure to respond to defendant’s May 2019 supplemental discovery demands (motion sequence 005). (See NYSCEF No. 129.) Plaintiff opposed, arguing that (i) the supplemental demands sought irrelevant information about one of plaintiff’s car-rental facilities at a different location in Brooklyn and about internal policy documents of plaintiff and in any case (ii) plaintiff had now turned over all documents in its possession that were responsive to those requests. (See NYSCEF No. 145.) In December 2019, plaintiff moved to strike defendant’s pleadings as a discovery sanction under CPLR 3126 (motion sequence 006). Plaintiff argued that defendant’s August 2019 response to plaintiff’s supplemental demands was not meaningful and flouted defendant’s obligations under the July 2019 so-ordered discovery stipulation and the January 2019 vacatur order. (See NYSCEF Nos. 150-161.) Defendant opposed, arguing that plaintiff’s supplemental document demands were overbroad and irrelevant and that defendant had fully complied with his discovery obligations by objecting to those demands. DISCUSSION Striking a party’s pleading is a drastic measure. Courts should not invoke their discretion to strike unless “the resisting party’s default is shown to be deliberate and contumacious.” (Eagle Star Ins. Co. of Am. v. Behar, 207 AD2d 326, 326 [2d Dept 1994].) This court concludes that given the history of this litigation, defendant’s failure to respond meaningfully to plaintiff’s supplemental document demands meets this high standard. This action, though commenced in 2015 and involving a single plaintiff and single defendant, is not yet ready for depositions. Defendant previously failed to produce any documents in discovery for more than two years after plaintiff first served its document demands. And this court has twice required defendant to pay increasing amounts in attorney fees, and commit to complying with discovery orders, as a condition of vacating orders that had stricken defendant’s pleadings on default. Plaintiff now contends that defendant’s refusal to produce any documents in response to plaintiff’s supplemental demands willfully flouts defendant’s obligation to respond meaningfully to those supplemental demands, as required by the parties’ July 2019 stipulation — so-ordered by this court — and the court’s February 2019 order. This court agrees. Plaintiff’s supplemental demands, though broadly drafted, seek relevant and material information.1 Plaintiff’s claims here are based on allegations that defendant led them to believe that he would lease his property to them (and to help them take the steps necessary to enable their use of the site), while at the same time quietly finding another, more lucrative tenant or purchaser who would be using the site for a different, incompatible purpose. (See Complaint, NYSCEF No. 5, at 2-5.) Plaintiff’s supplemental demands are tied to this basic theory of the case: seeking, for example, documents that would identify prospective purchasers or tenants for the property during the relevant period (and the property’s current owner or tenant), communications between defendant and potential purchasers or lessees, any broker who served as the intermediary for those interactions, agreements between defendant and the residential developer who did purchase the property, and the identity of the broker used in that purchase. (See generally NYSCEF No. 153.) Defendant did not produce any documents in response to this set of demands. Nor did he assert particular objections tailored to particular aspects (or flaws) of individual demands. Instead, he gave an identical response for each demand: that he objects to the demand “to the extent that it is not relevant, vague and ambiguous, redundant, overly broad, not properly limited in time or scope, [and] not reasonably calculated to lead to the discovery of admissible evidence,” and also “to the extent it seeks information protected from discovery by the attorney-client privilege.” (Objections & Responses, NYSCEF No. 128, passim.) Plaintiff and this court are thus left merely to guess about what defendant finds objectionable with respect to any particular document demand. Defendant asserts that he complied with the July 2019 stipulation because he merely raised objections to the supplemental demands, as the stipulation permitted him to do. This court disagrees. That defendant could object to improper or irrelevant discovery requests did not mean that he was entitled to interpose any objection he saw fit regardless of its merits. Nor is there merit to defendant’s argument that it would be premature to strike his answer here because plaintiff did not first move to compel after receiving defendant’s supplemental response. In the unusual circumstances of this litigation, plaintiff could readily have concluded that moving to compel would accomplish little beyond wasting time and resources (both its own and those of this court). This court is cognizant that striking a party’s pleadings is a drastic discovery sanction, not to be reached for lightly. Yet in the circumstances presented here, this court concludes that granting plaintiff’s motion to strike is the only appropriate sanction that will adequately address defendant’s sustained, willful, deliberate, and contumacious behavior. Plaintiff’s motion to strike defendant’s answer (motion sequence 006) is granted. In light of this court’s conclusion on motion sequence 006, defendant’s own motion to strike plaintiff’s complaint is denied as academic. Accordingly, it is hereby ORDERED that plaintiff’s motion to strike defendant’s answer under CPLR 3126 (motion sequence 006) is granted, and the answer is stricken; and it is further ORDERED that defendant’s motion to dismiss plaintiff’s complaint under CPLR 3126 (motion sequence 005) is denied as academic; and it is further ORDERED that plaintiff shall e-file a note of issue in this action on NYSCEF and serve it on defendant and on the General Clerk; and it is further ORDERED that upon such service, the General Clerk shall calendar this matter for an inquest to determine damages. Dated: May 12, 2020