From Craft v. Flagg, 2009 U.S. Dist. LEXIS 23529 (N.D. Ill. Mar. 20, 2009):

Federal Rule of Civil Procedure 36(b) invests discretion in the Court to permit a party to withdraw admissions. Banos v. City of Chicago, 398 F.3d 889, 892 (7th Cir. 2005). Rule 36(b) provides:

A matter admitted under this rule is conclusively established unless the court, on motion, permits the admission to be withdrawn or amended. Subject to Rule 16(e), the court may permit withdrawal or amendment if it would promote the presentation of the merits of the action and if the court is not persuaded that it would prejudice the requesting party in maintaining or defending the action on the merits.

Both the merits and prejudice prong of Rule 36(b) should be satisfied before withdrawal is permitted. DeCola v. Kosciusko County Sheriff's Department, 2007 WL 1650921, at *2 (N.D. Ind. June 5, 2007).

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[T]he prejudice prong of the Court's inquiry weighs heavily in favor of denying Plaintiffs' Motion [to withdraw their admissions, which were admitted by failure to respond]. For purposes of a Rule 36(b) Motion to Withdraw, courts recognize that prejudice "does not simply mean that the party who obtained the admissions will now have to argue the merits of the case. Rather, the prejudice must be based on the party's detrimental reliance on such admissions." Paymaster Corp. v. Cal. Checkwriter Co., No. 95 C 3646, 1996 WL 543322, at *2 (N.D. Ill.1996) (citing Hadley v. United States, 45 F.3d 1345 (9th Cir.1995)).

Defendants have made such a showing in this case. This is not a case where Plaintiffs' Responses were a few days or even a few weeks late. See Matthews v. Homecoming Financial Network, 2006 WL 2088194, at * 3 (N.D Ill. July 20, 2006). T o the contrary, Plaintiffs waited more than 60 days, and after Defendants completed twelve depositions, to file their Answers. Plaintiffs then waited almost six weeks more to file the Motion to Withdraw Admissions, long after Defendants had reminded them of the consequences of their delays.

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…Defendants reasonably relied upon the admissions in deposing all twelve of the Plaintiffs. Discovery in this matter has been lengthy, costly, and complex. Defendants filed their Requests for Admissions in July, and did not oppose Plaintiffs initial request for an extension, as the Plaintiffs' Responses were due on October 8, 2008 —weeks before the scheduled depositions. Defendants then prepared for and conducted the depositions of all twelve Plaintiffs in reliance upon the admissions, tailoring their questioning accordingly.

Although Plaintiffs' counsel purportedly spent considerable time preparing his clients, he did not attend the depositions. While Plaintiffs' counsel did not invest a significant amount of his time at the depositions, the Defendants' investment was considerable. To permit Plaintiffs to withdraw their admissions at this point would likely necessitate that Defendants undertake the costly and time-consuming task of redeposing these Plaintiffs. Defendants would clearly be prejudiced if the Court permitted the withdrawal. As the Advisory Committee Notes to Rule 36 state, "[u]nless the party securing the admission can rely on its binding effect, he [or she] cannot safely avoid the expense of preparing to prove the very matters on which he [or she] has secured the admission, and the purpose of the Rule is defeated." As such, the Court denies Plaintiffs' Motion to Withdraw Admissions Pursuant to Rule 36(b) [# 310].