OPINION AND ORDER In his relatively short career litigating in this District, Richard Liebowitz has earned the dubious distinction of being a regular target of sanctions-related motions and orders. Indeed, it is no exaggeration to say that there is a growing body of law in this District devoted to the question of whether and when to impose sanctions on Mr. Liebowitz alone. See, e.g., Pereira v. 3072541 Canada Inc., No. 17-CV-6945 (RA), 2018 WL 5999636, at *2 (S.D.N.Y. Nov. 15, 2018); McDermott v. Monday Monday, LLC, No. 17-CV-9230 (DLC), 2018 WL 5312903, at *2-3 (S.D.N.Y. Oct. 26, 2018) (citing cases); Steeger v. JMS Cleaning Servs., LLC, No. 17-CV-8013 (DLC), 2018 WL 1363497, at *3 (S.D.N.Y. March 15, 2018); Craig v. UMG Recordings, Inc., No. 16-CV-5439 (JPO), 2019 WL 1432929, at *10 (S.D.N.Y. Mar. 29, 2019). This Opinion is the latest contribution to that body of law. For the reasons stated below, the Court concludes that sanctions should indeed be imposed on Mr. Liebowitz for his repeated failure to comply with this Court’s orders, failures that imposed considerable and unwarranted costs on the Court, its staff, and Defendant NBCUniversal Media, LLC. BACKGROUNDPlaintiff John Curtis Rice filed this Complaint, bringing claims under the Copyright Act, 17 U.S.C. §101 et seq., on January 16, 2019. See Docket No. 1. The Complaint alleges that Defendant NBCUniversal Media, LLC, infringed Rice’s rights by displaying a copyrighted photograph — depicting the removal of a wild racoon from a beauty shop in the Bronx — on one of its websites. See id. More specifically, the Complaint alleges that “NBC did not license the Photograph from Plaintiff for its article, nor did NBC have Plaintiff’s permission or consent to publish the Photograph on its Website.” Id.11; see also id.13 (“NBC is not, and has never been, licensed or otherwise authorized to reproduce, publically display, distribute and/or use the Photograph.”). On January 17, 2019, the Court ordered that the parties appear for an initial conference on May 2, 2019, and ordered them to conduct a mediation session prior to that initial conference. See Docket Nos. 6, 7.NBCUniversal maintains — as it has since early in the case, see Docket No. 34 (“Transcript” or “Tr.”), at 2-3 — that it did not infringe Plaintiff’s copyright because it had a license for online use of Plaintiff’s photograph. See, e.g., Docket No. 15, at 31 (providing the affirmative defense that “NBCUniversal had the express and/or implied license to utilize the Photograph”); Docket No. 16, at 2. In or about mid-March 2019, according to defense counsel, NBCUniversal “produced the evidence supporting its complete license defense” by disclosing to Liebowitz a $200 invoice for “the online Today Show use of the…image of Raccoon capture, Bronx, NY.” Docket No. 27 (“Lerner Decl.”)