OPINION AND ORDER
SIDNEY H. STEIN, District Judge.
For about five years, both this Court and Magistrate Judge Debra Freeman have been attempting to administer this case to a conclusion, despite the inaction, repeated neglect of deadlines, and violations of court orders by both sides, culminating in plaintiff's complete failure to respond to the Court's recent order to show cause why the action should not be dismissed with prejudice. The time has come to terminate this litigation.
The Court certainly recognizes that Lehman's pro se status entitles him to "special leniency regarding procedural matters." See LeSane v. Hall's Sec. Analyst, Inc., 239 F.3d 206, 209 (2d Cir. 2001). But the Court ultimately concludes that despite "ample opportunity to pursue his case, " Lehman has failed to do so. See Ruzsa v. Rubenstein & Sendy Attys at Law, 520 F.3d 176, 178 (2d Cir. 2008) (per curiam). The Court therefore sua sponte exercises its inherent authority to dismiss Lehman's claims with prejudice. See United States ex rel. Drake v. Norden Sys., Inc., 375 F.3d 248, 250 (2d Cir. 2004); Fed.R.Civ.P. 41(b). In light of the Court's dismissal of Lehman's claims, the Court declines to exercise jurisdiction over Garfinkle's state-law counterclaim.
This action was originally brought by Lehman against Garfinkle and certain other defendants. The other defendants successfully moved to dismiss the complaint against them, and the action resolved itself into a litigation between pro se plaintiff Lehman and pro se defendant Garfinkle. By November 2011, Judge Freeman noted that Lehman had done "little to prosecute this action" in the preceding twelve months. (Order of M.J. Freeman dated Mar. 7, 2013, Dkt. No. 38, at 6.) In order to move the case forward, Judge Freeman held a case management conference that month with both Lehman and Garfinkle, explained the discovery process, and set various deadlines, including for discovery and for any motions to amend the pleadings. (Dkt. Nos. 29, 30, 33.)
Lehman subsequently sought both an extension of the discovery deadline and an extension of time in which to file an amended complaint, "even though, by that time, the deadline for any motions to amend had passed by nearly three months." (Order of M.J. Freeman dated Sept. 14, 2012, Dkt. No. 33, at 1.)
In September 2012, Judge Freeman held another case management conference, at which the parties explained that "despite the Court's having explained the discovery process to them in November 2011, they had essentially conducted no discovery, whatsoever." ( Id. at 1.) Despite that fact, "in recognition of the parties' pro se status, " the Magistrate reopened fact discovery and set new deadlines for its completion. ( Id. at 1-2.) Also, in consideration of the fact that Lehman was proceeding pro se, Judge Freeman gave Lehman "one final opportunity to file a proper motion to amend his complaint, " by September 28, 2012. ( Id. at 3.) Unable to meet that new deadline, and after Judge Freeman granted yet another extension, Lehman filed a motion to amend on October 4, 2012. ( See Order of M.J. Freeman dated Mar. 7, 2013, Dkt. No. 38, at 7.)
Following additional motion practice, this Court, by order dated April 12, 2013, directed the parties to "inform the Court in writing by April 26, 2013 whether they require any additional time for discovery" and set May 31, 2013 as the deadline for any motions for summary judgments to be filed. ( See Order dated Apr. 12, 2013. Dkt. No. 42, at 1.) Each of those deadlines passed without any response from either Lehman or Garfinkle. ( See Order dated July 30, 2013, Dkt. No. 43.)
In light of the fact that the parties had neither filed motions for summary judgment nor requested additional time for discovery, in an order dated July 30, 2013, the Court set a trial date of December 2, 2013. ( See id. ) The Court also ordered that the parties submit a joint pretrial order in conformity with the Court's individual practice rules, as well as any proposed jury charges and any proposed jury voir dire, on or before September 9, 2013. Given the history of this litigation, the Court notified the parties in that Order that "[f]ailure to do so will result in sanctions, including the possibility of a judgment of dismissal of all claims and counterclaims, with prejudice." ( Id. )
Neither party complied with the Court's July 30 order in any respect. As a result, on September 24, 2013, the Court ordered the parties to show cause by October 4, 2013 why the Court should not dismiss all claims and counterclaims, with prejudice. ( See Order dated Sept. 24, 2013, Dkt. No. 44.) To date, the Court has received no response whatsoever from Lehman, although it did receive a request from Garfinkle to stay the action for an indefinite period.
III. LEHMAN'S CLAIMS SHOULD BE DISMISSED WITH PREJUDICE
To determine whether a dismissal with prejudice pursuant to Rule 41(b) is warranted, courts consider five factors, namely whether:
(1) the plaintiff's failure to prosecute caused a delay of significant duration; (2) plaintiff was given notice that further delay would result in dismissal; (3) defendant [is] likely to be prejudiced by further delay; (4) the need to alleviate court calendar congestion [outweighs] plaintiff's right to an ...