OPINION OF THE COURT
Sandler, J.
This is an appeal by the defendants, Michael Schmertzler and Morgan Stanley & Co. Incorporated, from Special Term’s October 8, 1985 order granting the motion of the plaintiff, Shearson Lehman Brothers Holdings, Inc. (Shearson), for a [218]*218preliminary injunction prohibiting Schmertzler from performing investment banking services for Morgan Stanley in the New York City metropolitan area, upon a finding that the performance of such services by Schmertzler would violate terms of a noncompetition agreement that he signed in connection with the acquisition by Shearson of all of the stock of Lehman Brothers Kuhn Loeb Holding Co., Inc. (Lehman Brothers), including the stock Schmertzler owned as a shareholder-employee of Lehman Brothers.
In our opinion, plaintiff failed to sustain its burden of satisfying any of the three familiar requirements for the issuance of a preliminary injunction, which are to clearly demonstrate: (1) likelihood of success on the merits, (2) irreparable injury in the absence of a preliminary injunction, and (3) a balancing of the equities in favor of the party seeking an injunction. (See, e.g., Faberge Intl., v Di Pino, 109 AD2d 235, 240.)
Whether Shearson sustained its burden of clearly demonstrating the likelihood of ultimate success on the merits presents a close and complex question which, for reasons that will be developed later, we believe should have been resolved in favor of defendants. The questions presented with regard to the two remaining elements do not seem as close.
There is simply no evidence in this record that without a preliminary injunction Shearson will be irreparably injured if Schmertzler, who had not engaged in investment banking services in the New York metropolitan area for more than two and one-half years before his employment by Morgan Stanley, is permitted to perform such services on behalf of one of the many financial concerns in this city whose activities embrace investment banking. Indeed, the record discloses no persuasive evidence that Schmertzler’s performance of investment banking services in the metropolitan area would impair in any way the good will Shearson acquired when it purchased the stock of Lehman Brothers. Upon analysis, Special Term’s conclusion is seen to rest primarily upon speculation that if a preliminary injunction were not granted, there might result an exodus from Shearson of others who had signed the non-competition agreement, a speculation unsupported by even a shred of evidence pointing to any other employee in a situation comparable to that of Schmertzler.
Moreover, upon consideration of all of the relevant circumstances, it is apparent that the equities tip strongly in favor of [219]*219the defendants. What unmistakably appears from the record is that Schmertzler has been enjoined from investment banking activities in the metropolitan New York City area although it is clear that the parties to the agreement did not then intend any such result. This conclusion is underlined by an aspect of the transaction that appears to have been overlooked by Special Term in its otherwise comprehensive opinion.
Schmertzler was one of a small group of managing directors of Lehman Brothers (in effect partners) with a minimum stock allotment who were asked to sign a noncompetition agreement. The record is persuasive that this group, a small minority of those directors who held minimum stock ownership, were asked to sign because of the nature of their assignments at Lehman Brothers at the time of the acquisition, none of them being then involved in investment banking, and not because of responsibilities that they had previously discharged. No managing director with comparable stock ownership in Lehman Brothers’ Investment Banking Department at the time of the acquisition was asked to sign the noncompetition agreement, although it is indisputable that each of them was then far more significantly identified with Lehman Brothers’ investment banking activities than any of those asked to sign, including Schmertzler. In short, a perplexing situation is presented in which Schmertzler has been enjoined from investment banking activities in the New York metropolitan area on the basis of an agreement he was asked to sign for reasons unrelated to investment banking, while those managing directors with comparable stock ownership actively engaged in investment banking at the time of the acquisition, all of whom received the same consideration for their stock as Schmertzler, remained free, individually or collectively, to leave Shearson and actively compete with it in the investment banking business.
On or about April 17, 1984, Shearson and Lehman Brothers entered into an agreement pursuant to which Shearson was to acquire Lehman’s business for $317 million. The acquisition was effected through three interrelated agreements with the managing directors of Lehman Brothers—shareholder-employees who collectively owned all of the stock. First, the parties entered into a "Stock Purchase Agreement” whereby Shear-son acquired the stock of Lehman Brothers that had been outstanding for over one year. Second, by a "Stock Option Agreement” Shearson acquired an option to purchase those [220]*220shares which had been outstanding for less than a year. (The option arrangement was adopted at the request of stockholders who wished to secure capital gain treatment on the sale of this stock.) Finally, a majority of stockholders (according to an affidavit submitted on behalf of Shearson, some 57 out of 92 stockholders) were asked to sign, and did sign, noncompetition agreements. Schmertzler, one of the managing directors who signed the agreement, owned 500 shares, or 0.49%, of the outstanding common stock, that amount being the minimum share allocated to Lehman managing directors.
In this action by Shearson seeking, inter alia, to enjoin Schmertzler’s employment with Morgan Stanley & Co., Incorporated, as violative of the terms of the noncompetition agreement, the principal issue raised concerned the construction, reasonableness and legality of section 1 (c) of the noncompetition agreement. That section reads as here pertinent:
"1. Covenant Not to Compete. For a period commencing upon the consummation of the transactions contemplated by the Agreement for Purchase of Stock and ending on the third anniversary of the Closing Date, the Certain Stockholder will not, directly or indirectly, as a sole proprietor, member of a partnership, or stockholder, investor, officer or director of a corporation, or as an employee, agent, associate or consultant of any person, firm or corporation other than Lehman Brothers Kuhn Loeb Holding Co., Inc., or a successor corporation ('LBKL Holding’) or one of its Subsidiaries * * *
"(c) Engage in any business within a 90 mile radius of the metropolitan area in which the Certain Stockholder conducted substantial business for the twelve month period preceding the Closing Date which is in substantial competition with any substantial business conducted in such area, at the time such engagement is commenced, by LBKL Holding or its Subsidiaries and in respect of which the Certain Stockholder had substantial responsibilities during the term of his employment by LBKL Holding and its Subsidiaries ('Prohibited Activity’)”.
The essential facts relating to Schmertzler’s employment with Lehman Brothers and his responsibilities subsequent to the acquisition appear to be undisputed, although understandably the opposing affidavits stress different aspects of his services.
Schmertzler joined Lehman Brothers on or about September 1, 1977 as an investment banking associate in Lehman Brothers’ New York office. He was quickly evaluated as an associate [221]*221of exceptional promise and over the years was given increasingly important responsibilities and received substantial increases in compensation as he progressed rapidly through the firm. In April 1981, Schmertzler was designated by the head of Lehman Brothers’ International Investment Banking Department as his "top assistant”, the department consisting additionally of 5 managing directors and some 10 associates. In that capacity he participated with the head of the department in the over-all planning and strategy of the department, supervised the work of the associates, and participated significantly in a number of important transactions. However, Schmertzler, as an associate, could not, as a matter of company policy, undertake certain responsibilities which were reserved to managing directors. These responsibilities included such matters as accepting representation of clients, negotiating fee arrangements, committing Lehman’s capital to support underwritings, signing opinions, and formulating final recommendations to clients.
In December 1982, Schmertzler was asked to forego his corporate finance activities to become an administrator of the firm, first as chief financial officer, and then, still as an associate, as chief administrative officer. In these positions, Schmertzler was supervised by two of the most senior Lehman officers. Defendants assert without contradiction that he was instructed not to engage in investment banking business for the firm, and there is no persuasive evidence that he in fact did so during the period commencing in January 1983 and extending until after the acquisition of Lehman Brothers by Shearson in April 1984.
In September 1983, Schmertzler was elected a managing director and was invited to purchase 500 shares of Lehman stock, the minimum allotment to all new managing directors, which represented less than one half of 1% of Lehman stock at the time of the acquisition.
In July 1984, after the acquisition, Schmertzler was appointed head of Shearson’s International Investment Banking Department and relocated to London to discharge those responsibilities. For reasons not relevant to the issues in this case, Schmertzler decided to seek other employment, and entered into discussions with Morgan Stanley in April 1985. On May 7, 1985, Schmertzler accepted an offer of employment in the area of investment banking with Morgan Stanley, resigning from Shearson effective May 11, 1985. During May 1985, and before Schmertzler started to work for Morgan [222]*222Stanley, the principals of that company negotiated with Shearson in an effort to reach an agreement defining the responsibilities Schmertzler might discharge with Morgan Stanley that would not be considered by Shearson as a violation of the noncompetition agreement. These negotiations having failed, Shearson commenced this lawsuit against Schmertzler for breach of the noncompetition agreement, and against Morgan Stanley for tortious interference with that agreement, simultaneously moving for a preliminary injunction.
In granting the injunction, which broadly prohibited Schmertzler from performing investment banking duties for Morgan Stanley within a 90-mile radius of the World Trade Center, Special Term concluded that the noncompetition agreement was valid and enforceable; that the term "substantial responsibilities” in the noncompetition agreement was clear and unambiguous, therefore excluding consideration of parol evidence; that Schmertzler had discharged such responsibilities both before and after the acquisition; and that Shear-son had sustained its burden of establishing the above-described elements required for a preliminary injunction. We disagree with essential aspects of Special Term’s findings, and accordingly would reverse the order appealed from to deny the motion for a preliminary injunction.
Analysis of the issues presented appropriately starts with a restatement of the governing rules of law that have been developed with regard to the legality and enforceability of noncompetition agreements. In what continues to be an authoritative exposition of those principles, the Court of Appeals in Purchasing Assoc. v Weitz (13 NY2d 267) observed that a distinction had developed between the rules governing such covenants when incident to the sale of a business, and covenants given by employees that do not accompany such a sale. As developed in the opinion, covenants not to compete incident to the sale of a business are more liberally enforced "on the premise that a buyer of a business should be permitted to restrict his seller’s freedom of trade so as to prevent the latter from recapturing and utilizing, by his competition, the good will of the very business which he transferred for value * * * This court has applied the 'sale of a business’ rationale where an owner, partner or major stockholder of a commercial enterprise has sold his interest for an immediate consideration which was, in part, payment for the good will of the business” (supra, at p 271). As further set forth in the opinion, the sole [223]*223limitation on such a covenant is that the restraint must be reasonable, "that is, not more extensive, in terms of time and space, than is reasonably necessary to the buyer for the protection of his legitimate interest in the enjoyment of the asset bought” (supra, at pp 271-272).
In distinction to covenants incident to the sale of a business, the court pointed out that a covenant given by an employee that he will not compete with his employer has been regarded much more strictly because of the "powerful considerations of public policy which militate against sanctioning the loss of a man’s livelihood” (13 NY2d, at p 272). Such covenants are "enforced only to the extent necessary to prevent the employee’s use or disclosure of his former employer’s trade secrets, processes or formulae * * * or his solicitation of, or disclosure of any information concerning, the other’s customers” (supra, p 272). In addition, however, if the employee’s services are unique or extraordinary, the covenant may also be enforced by injunctive relief, if reasonable, even though the employment did not involve trade secrets or confidential customer lists.
Preliminarily, we do not accept defendants’ threshold contention that section 1 (c) of the noncompetition agreement should be considered unenforceable as being in essence an employment agreement because of Schmertzler’s minimal ownership interest. In advancing this contention, defendants rely on the passing comment by the Court of Appeals in Purchasing Assoc. v Weitz (supra, at p 271) with reference to the enforcement of noncompetition agreements where it is incident to a sale by "an owner, partner or major stockholder of a commercial enterprise”, and the holding in that case under circumstances clearly different from those here presented, that the noncompetition agreement was essentially an employment contract in character although purporting to accompany sale of a business.
Although no case has been called to our attention in which a noncompetition agreement of the character presented has been enforced with regard to someone with so small an ownership interest as that of Schmertzler, and the single appellate decision involving comparable ownership found a noncompetition agreement unenforceable (White v Fletcher/ Mayo/Assoc., 251 Ga 203, 303 SE2d 746), we are persuaded that this defense contention is ultimately untenable. Its adoption would place an unacceptable barrier in the path of sales of businesses in which ownership is widely diversified, and in [224]*224which, as here, good will is clearly a central concern in the acquisition.
On the other hand, there is a clear, realistic difference between the problem presented by the application of a non-competition agreement to someone with a minimal ownership interest, and its application in the more familiar situation to the principal of a company being sold, or one of several principals of the company being sold, where their identification with the company sold is so significant and pronounced that subsequent competition would inevitably impair the value of that which was bought. This difference may well, when accompanied by other relevant circumstances, justify a different approach in evaluating the reasonableness of the agreement and the appropriateness of injunctive relief.
Turning now to the construction of section 1 (c) of the noncompetition agreement, and in particular to the meaning of the phrase "substantial responsibilities”, we disagree with Special Term’s conclusion that this term is clear and unambiguous, that parol evidence bearing on its meaning therefore may not be considered, and that the services rendered as an investment banker by Schmertzler as an associate more than a year prior to Shearson’s acquisition of Lehman Brothers were clearly "substantial responsibilities” within the meaning of section 1 (c). This determination is plausible only if, contrary to the established rules governing the construction of agreements, the words "substantial responsibilities” are separated from the context of the agreement in which they appear, and viewed in the abstract. When viewed realistically in the business context in which the agreement was signed, the conclusion seems to us compelling that the meaning of the term was at best, from plaintiff’s viewpoint, ambiguous.
The noncompetition agreement was signed incident to the sale of stock, the ownership of which was widely diversified among the managing directors of Lehman Brothers. Although most of the managing directors of Lehman Brothers were asked to, and did, sign the noncompetition agreement, many were not asked to sign, including a substantial majority of those with the minimum stock ownership held by Schmertzler. The small minority of stockholders owning 500 shares who were asked to sign appear to have been selected because of some characteristic of the duties they were performing at the time of the acquisition, without the slightest intimation in this record that any study was undertaken by Shearson with regard to their prior services, including services performed as [225]*225associates. As already pointed out, not a single managing director with comparable stock ownership then in the Investment Banking Department of Lehman Brothers was asked to sign, although it is a realistic assumption that the duties they were then discharging were at least as important as those discharged by Schmertzler more than a year previously as an associate, and although they were far more significantly identified than Schmertzler with Lehman Brothers’ investment banking activities at the time of the acquisition.
Considering these circumstances as a whole, it is a reasonable inference that the agreement omitted to state specifically that "substantial responsibilities” referred to services performed by managing directors only because this was the common assumption of the parties to the agreement. This interpretation is confirmed by the uncontradicted parol evidence presented to Special Term, which under the circumstances should have been considered, but was not. The principal negotiators for Lehman Brothers deposed that it was never contemplated that the words "substantial responsibilities” embraced services performed by associates. It is not without significance that the senior attorney in the law firm that represented the managing directors of Lehman Brothers at the time the agreement was negotiated, who, at the time of this litigation, had a disinterested position between the parties, was willing to submit an affidavit as to the intended meaning of the clause if permitted to do so by Shearson, and that Shearson withheld that permission.
A closer, more complicated question is presented with re-. gard to the duties discharged by Schmertzler in London after the acquisition in his capacity as head of international investment banking for the successor firm. Undeniably these services constituted "substantial responsibilities” within the meaning of section 1 (c). The immediate question presented is whether the agreement applies to services rendered after the acquisition of Lehman Brothers, and if so, whether the agreement is enforceable with regard to such postacquisition activities.
Preliminarily, we believe that plaintiff is clearly correct in its contention that as a matter of construction the agreement extends the noncompetition commitment to postacquisition substantial responsibilities. This conclusion seems inescapable in light of the definition of "LBKL Holding” as including Lehman Brothers Kuhn Loeb Holding Co., Inc., or a successor [226]*226corporation. On the other hand, we think it doubtful that the parties in fact intended what the agreement plainly stated.
Whether or not it is appropriate even with regard to a weighing of equities as it relates to a preliminary injunction to consider indications that the parties did not mean what an agreement clearly says presents a troublesome question that is unnecessary to decide here. The circumstances which give rise to doubt that the parties intended the noncompetition agreement to apply to postacquisition responsibilities are independently relevant to a consideration of issues on this appeal.
What becomes apparent from a study of the clause is the controlling importance given to the date of acquisition. The three-year term of the agreement not to compete starts on that date, and the section prohibits a signer from engaging in any business within a 90-mile radius of the metropolitan area in which he conducted substantial business "for the 12-month period preceding the closing date”. Construing the agreement in accordance with plaintiffs interpretation, and what we accept as its plain meaning, the inexplicable anomaly is presented that a signer who conducted business in one metropolitan area (when he worked for Lehman Brothers) during the year prior to the acquisition, and who was thereafter given substantial responsibilities in another metropolitan area (when he worked for Shearson), is prohibited from competing with Shearson in regard to such responsibilities in the area in which he did substantial business prior to the merger, and not in the area in which he was more currently discharging his duties for Shearson. This is, in fact, what occurred with respect to Schmertzler, whose duties as head of Shearson’s International Banking Department were discharged in London, and who has been enjoined from performing investment banking services in the New York City metropolitan area. It is not easy to believe that the sophisticated parties to this agreement intended so apparently absurd a result, and one so doubtfully related to any appropriate interest of Shearson in preserving the good will it had acquired.
Construing the noncompetition agreement, in accordance with its literal meaning, to apply to postacquisition responsibilities, a serious question is presented as to whether that aspect of the agreement may be sustained as reasonably incident to Shearson’s acquisition of Schmertzler’s minimal stock in Lehman Brothers. The issue is a close one, there appearing to be no prior authority clearly addressing it in a relevant context, and it may well be prudent for its ultimate [227]*227resolution to await a fuller development of circumstances than is now before us. But on the face of it, the agreement as so applied seems to assume preponderantly the aspects of a separate employment agreement, and is not enforceable as such under the circumstances here presented.
The good will that Shearson acquired as part of its purchase of outstanding stock of Lehman Brothers was surely that which existed at the time of the acquisition. During the period that Schmertzler discharged his postacquisition duties in London he was an employee of Shearson, and no longer a stockholder. To enlarge the scope of Schmertzler’s covenant not to compete on the basis of responsibilities that were assigned to him as an employee after the acquisition, seems to transform the character of the noncompetition agreement at least to some extent from one incident to the sale of a business to that of a separate employment agreement. Recognizing that the answer to the question is not free from doubt, the issue seems sufficiently substantial to preclude a finding that Shearson has demonstrated the likelihood of ultimate success on the merits.
In evaluating whether or not Shearson has satisfied the requirement of showing that it would sustain irreparable injury in the absence of a preliminary injunction, an issue already addressed briefly in this opinion, it is important to distinguish the situation here presented from the more familiar one in which a principal, or a few principals in a firm, sign noncompetition agreements incident to the sale of the business, and in which it is clear that the entry of any one of them into a competing business would impair the good will that had been acquired. The same inference might well have been appropriate here if we were presented with a competitive activity by one of Lehman Brothers’ principal managing directors at the time of the acquisition. That conclusion does not seem to follow quite so readily with regard to a managing director with minimal stock ownership who, as the record strongly indicates, was asked to sign the noncompetition agreement only because of his contemporaneous role in the administration of Lehman Brothers, and wholly without regard to the area of activity that is the subject of this action.
As to Schmertzler’s services as an associate more than one year prior to the acquisition, it seems free from doubt that those activities would not, without more, justify an inference that his employment as an investment banker with Morgan Stanley would seriously impair the good will embraced in Shearson’s acquisition of Lehman Brothers. On this issue we [228]*228think it dispositive that no managing director in Lehman Brothers’ Investment Banking Department with comparable ownership was asked to sign the noncompetition agreement. In the absence of anything in this record to the contrary, the inference is compelling that their services were at least as important, if not more so, than those rendered by Schmertzler as an associate, and that they were more significantly identified with the investment banking activities of Lehman Brothers in the New York metropolitan area at the time of the acquisition than he was. The failure to ask any of them to sign the noncompetition agreement seems conclusive that Shearson did not believe that there would be an impairment of the good will that was acquired if those directors individually or collectively accepted employment as investment bankers with competing financial concerns. The same conclusion would seem to follow a fortiori with regard to investment banking services performed by Schmertzler as an associate some time before the acquisition.
Undoubtedly a closer question is presented by Schmertzler’s postacquisition services as head of Shearson’s International Banking Department in London. It is at least possible that in the course of those duties he became so identified with Shear-son’s investment banking activities that upon his accepting employment in the New York City metropolitan area, investment banking business would come to him in his new employment that might otherwise have gone to Shearson. Nothing in the record, however, provides any tangible support for this hypothesis, and against it must be weighed the central importance assigned in the noncompetition agreement to the geographical areas in which signing directors had conducted substantial business, and the doubtful, if not clearly unreasonable, character of an agreement that precludes a signer from working in one geographical area on the basis of responsibilities that he had assumed after the acquisition in another geographical area, although it does not restrain him from competing in the area in which he had in fact discharged those responsibilities.
In finding that Shearson had satisfied its burden of establishing irreparable damage if a preliminary injunction were not issued, it is apparent that Special Term was primarily influenced by a fear that a refusal to grant the motion for a preliminary injunction might somehow encourage an exodus to competing financial firms from Shearson of other Lehman Brothers managing directors who had signed. The record [229]*229discloses no support for this concern. What is immediately apparent is that Schmertzler’s situation was an unusual one, quite possibly unique, among those who had signed the agreement, and it is far from clear, and certainly not established in this record, that any other signer occupied a position sufficiently comparable to that of Schmertzler to support Special Term’s stated fear. More than unsupported speculation is required before a preliminary injunction can issue significantly constraining an individual’s employment on the basis that irreparable damage would follow failure to grant such an injunction.
For reasons set forth at different points in this opinion, it seems clear that a balancing of the equities at this point of the litigation tip strongly in favor of the defendants. To capsulize what has already been said, Shearson has secured a preliminary injunction prohibiting Schmertzler from engaging in investment banking activities in the New York metropolitan area on the basis of his supposed violation of a noncompetition covenant which he was asked to sign because of services he rendered wholly unrelated to investment banking, which the parties did not contemplate at the time of the agreement would in fact curtail his right to engage in investment banking, and which was part of a transaction in which a majority of managing directors with Schmertzler’s minimum stock interest, including all such directors then actively participating in investment banking, were not asked to sign. By any standard, the damage sustained by Schmertzler as a result of the preliminary injunction issued has been significantly greater than would have been sustained by Shearson if the preliminary injunction had not been granted, if indeed Shear-son would have sustained any damage at all.
Accordingly, the order of the Supreme Court, New York County (Martin Evans, J.), entered October 8, 1985, which granted plaintiff’s motion for a preliminary injunction prohibiting Schmertzler from rendering investment banking services in the New York City metropolitan area and prohibiting Morgan Stanley from employing Schmertzler to perform such services, should be reversed, on the law, on the facts, and in the exercise of discretion, to deny plaintiff’s motion for a preliminary injunction.