The opinion of the court was delivered by: Gabriel W. Gorenstein, United States Magistrate Judge
A. Proceedings Prior to the Instant Motion
On December 8, 2004, plaintiff Collette J. Scott filed this action pro se against defendants City of New York Department of Correction, the Correction Officers' Benevolent Association of the City of New York Inc. ("COBA"), and Norman Seabrook, alleging employment discrimination. See Complaint, filed Dec. 8, 2004 (Docket # 1). The original complaint contained allegations that Seabrook assaulted plaintiff by forcing her to kiss him, that she complained about his conduct, and that she was subsequently the subject of unwarranted charges and other retaliatory conduct, including an improper transfer. See id.
On June 22, 2005, the Court issued a scheduling order pursuant to Federal Rule of Civil Procedure 16. See Order Pursuant to Rule 16(b), filed June 22, 2005 (Docket # 22) ("Scheduling Order"). The Scheduling Order gave the parties a deadline of July 20, 2005 to move to amend the complaint and a deadline of October 28, 2005 to complete discovery. Id. at 1. Ten days before the discovery deadline, the Court granted, at Scott's request, a 30-day extension of all deadlines. See Memorandum Endorsement, filed Oct. 20, 2005 (Docket # 24). One month later, an attorney, Donnahue George, filed a notice of appearance for Scott, see Notice of Appearance, filed Nov. 17, 2005 (Docket # 25), and at his request the Court granted an additional 60-day extension of the original deadlines. See Memorandum Endorsement, filed Nov. 29, 2005 (Docket # 26). The time to move to amend thus expired on October 18, 2005.
Scott and the defendants became involved in various discovery disputes that were presented to the Court by letter. Following a courtroom conference on February 3, 2006, the Court again extended the discovery deadline, this time until April 14, 2006. See Order, filed Feb. 6, 2006 (Docket # 27). It did not, however, extend the deadline for moving to amend the complaint. The Court also ordered that plaintiff's deposition take place on March 8, 2006. See id. The deposition of plaintiff took place on March 8 and 9, 2006. See Memorandum of Law in Support of Plaintiff's Motion to Amend Complaint and Reopen Discovery, filed Dec. 29, 2006 (Docket # 58) ("Pl. Mem."), at 2. Plaintiff was represented by George during this deposition. See id.
Under the Scheduling Order, defendants' motion for summary judgment was due on May 12, 2006. See Scheduling Order. The City sought an extension of this deadline to May 26, 2006, which was granted. See Memorandum Endorsement, filed Apr. 20, 2006 (Docket # 30). On May 3, 2006, George wrote to the Court asserting that defendants had not complied with certain discovery requests. See Memorandum Endorsement, filed May 3, 2006 (Docket # 32). The Court instructed George to file an appropriate motion by May 10, 2006, and adjourned the summary judgment deadline sine die provided the motion was timely filed. See id. On that date, George filed a motion for sanctions against the defendants, see Notice of Motion, filed May 10, 2006 (Docket # 33), which was denied. See Order, filed July 6, 2006 (Docket # 38).*fn1 The Court adjourned the deadline for the summary judgment motions to July 31, 2006, see id. at 4 -- a deadline that was later extended to September 15, 2006, see Memorandum Endorsement, filed July 26, 2006 (Docket # 39), and subsequently extended to September 22, 2006. See Order, filed Sept. 19, 2006 (Docket # 45) ("Sept. 2006 Order"). The defendants duly filed their motions for summary judgment by that date.
On September 15, 2006, a courtroom conference was scheduled before Judge Stein, apparently at the request of Scott herself. After George did not appear, Judge Stein ordered George to show cause "as to why he should not be sanctioned . . . for his repeated failures to contact his client and his adversary." George did not submit papers opposing sanctions; nor did he appear at a hearing held on the matter. See Order, filed Oct. 30, 2006 (Docket # 49). The Court ultimately sanctioned him in the amount of $2,500. Id.
At about this time, Scott obtained new counsel. See Notice of Appearance by Susan B. Egan on Behalf of Collette J. Scott, filed Oct. 26, 2006 (Docket # 48). A conference was held on October 27, 2006, at which Scott's new counsel stated that she wished to take some discovery and to amend the complaint. See Transcript of Oct. 27, 2006 conference, filed Nov. 6, 2006 (Docket # 52), at 9-10. Defendant's counsel reported that Judge Stein had already indicated that he "wasn't predisposed to open the whole thing up," and had directed the filing of summary judgment motions. Id. at 11. The Court stated that, while it shared Judge Stein's views, the Court would not prevent plaintiff from making these motions and would set a schedule for them.
Scott then made the instant motion to amend her complaint and to reopen discovery -- the briefing of which was not concluded until late March 2007 as a result of both plaintiff's and defendants' multiple requests for extensions.*fn3 Plaintiff's motion papers addressed only the standards for amending the complaint and provided no argument at all as to why discovery should be re-opened. The defendants opposed the amendments not only on untimeliness and prejudice grounds, but also based on a failure to exhaust and other doctrines.
The Court held oral argument on the plaintiff's motion on June 18, 2007. See Transcript of June 18, 2007 conference, filed Aug. 22, 2007 (Docket # 81). At that proceeding, the Court noted that plaintiff's argument seemed contradictory inasmuch as plaintiff asserted that she was adding no new claims while at the same time the complaint was replete with new allegations and, it appeared, new causes of action. Id. at 3-4. Plaintiff stated that it was "not [her] intention" to add at least some of the claims. Id. at 4. During the course of the argument plaintiff seemed to argue that her intention was to make clear that certain claims were the result of sex discrimination, not just retaliation. Id. at 8-9. Plaintiff also asserted that "the stuff that's in the complaint as I've amended it has basically all been the subject of prior discovery and . . . other filings" -- referring to plaintiff's administrative charge. Id. at 10; accord id. at 13. Focusing on the prejudice issue, the Court pointed out that the defendants would have a much stronger argument in opposition to the proposed amended complaint if in fact there were "new claims that they have to defend against." Id. at 11. The Court noted that it would be a different situation if the new complaint consisted merely of the same claims that defendants had "deposed [plaintiff] about, that are in the EEOC charge." Id. The Court proposed that plaintiff make clear what specific incidents she was suing on and what the basis for her claim was with respect to each incident (for example, sex discrimination or retaliation). Id. at 11-12. The Court instructed that the claims should be identified "by a certain time period and a certain thing that happened to [plaintiff]." Id. at 12. Structuring the complaint in this way would enable the defendants to state whether these were new matters or not. Id. at 12-13. The Court instructed plaintiff to send this new complaint to each defendant so that the parties could reconvene for oral argument on the basis of the new complaint. Id. at 16, 23. The Court warned plaintiff that the broader she made her second proposed amended complaint, the better an argument the defendants would have that they would be prejudiced by its filing. Id. at 13.
On July 9, 2007, plaintiff submitted a new proposed amended complaint, see Letter from Susan B. Egan, filed Nov. 13, 2007 (Docket # 83), ...