This section is from the book "The Law Of Contracts", by Theophilus Parsons. Also available from Amazon: The law of contracts.
* With the exception of these rules of construction, which seem to have grown. out of the peculiar nature of this class taken to have meant that the sum agreed on was to be liquidated damages, and not a penalty. In this case there is no pecuniary stipulation, for which a sum certain, of less amount than £1,000, is to be paid, but all the stipulations are of uncertain value. Possibly this may have been a very imprudent contract for the defendant to make; but with that we have nothing to do. Upon the true construction of the deed, the amount is payable by way of liquidated damages, and not as penalty." See also Lee v. Whitaker, L. R. 8 C. P. 70; Magee v. Lavell, L. R. 9 C P. 107; Re Newman, 4 Ch. D. 724, Wallis v. Smith, 21 Ch. D. 243. The decision of Kerable v. Farreu was questioned by Gilchrist, J., in Brewster v. Edgerly, 13 N. H. 275, 278, but it has been generally recognized in this country as sound law. Williams v. Dakin, 17 Wend. 447, 455, 22 Wend. 201, 212; Niver v. Rossman, 18 Barb. 50; Jackson v. Baker, 2 Edw. Ch. 471; Heard v. Bowers, 23 Pick. 455; Shute v. Taylor, 5 Met. 61, 67, per Shaw, C. J.; Moore v. Platte Co. 8 Mo. 467; Gower v. Saltmarsh, 11 Mo. 271; Carpenter v. Lockhart, 1 Cart. (Ind.) 434, 443; Bright v. Rowland, 3 How. (Miss.) 398, 413; Cheddick v. Marsh, 21 N. J. 463; Curry v. Larer, 7 Pa. 470; Watts v. Camors, 115 U. S. 353; People v. Central Pac. R. R. Co. 76 Cal. 29; Carter v. Strom, 41 Minn. 522; State v. Dodd, 45 N. J. L. 525; March v. Allabough, 103 Pa. 335; Lyman c. Babcock, 40 Wis. 503. In the cases of Beale v. Hayes, 5 Sandf. 640, and Bagley v. Peddie, id. 192, this question has been ably discussed, and this rule established. The case of Beale v. Hayes arose out of a theatrical engagement, and was not distinguishable in its material facts from Kemble v. Farren, supra, which the court followed in deciding the case. In Bagley v. Peddie, the defendants were bound to pay "three thousand dollars, liquidated damages," in case A, one of the defendants, should refuse to continue with, or serve the plaintiff, or should violate any of several other coveuants contained in the agreements. Some of the covenants were clearly "certain in their nature, and the damages for their breach could be readily ascertained by a jury " The sum was held to be a penalty. Sandford, J., in delivering a very able opinion, said "The courts have leaned very hard in favor of construing covenants of this kind to be in the nature of penalties, instead of damages, fixed and stipulated between the parties, and in so doing have established certain rules which will serve to guide us in determining this case. It may, perhaps, be justly said, that in this struggle to relieve parties from what, on a different construction, would be most improvident and absurd agreements, the courts have sometimes gone very far towards making new contracts for them, somewhat varied from the stipulations, which, under other circumstances, would be deduced from the language they used; but we believe no common-law court has yet gone so far as to reduce the damages conceded to have been liquidated and stipulated between the parties, to such an amount as the judges deem reasonable, which is the course in countries where the civil law prevails. Among the principles that appear to be well established, are these: 1. Where it is doubtful, on the face of the instrument, whether the sum mentioned was intended to be stipulated damages, or a penalty to cover actual damages, the courts hold it to be the latter. 2. On the contrary, where the language used is clear and explicit to that effect the amount is to be deemed liquidated damages, however extravagant it may appear, unless the instrument be qualified by some of the circumstances hereafter mentioned. 3. If the instrument provide that a larger sum shall be paid, on the failure of the party to pay a less sum, in the manner prescribed, the larger sum is a penalty, whatever may be the language used in describing it 4. When the covenant is for the performance of a single act, or several acts, or the abstaining from doing some particular act or acts, which are not measurable by any exact pecuniary standard, and it is agreed that the party covenanting shall pay a stipulated sum as damages for a violation of any such covenants, that sum is to be deemed liquidated damages, and not a penalty. The cases of Reilly v. Jones, 1 Bing. 302; Smith v. Smith, 4 Wend. 468; Knapp v. Maltby, 13 id. 587; and Dakin v. Williams, 17 id. 447; s. c. in error, 22 id. 201, were of this class. 5. Where the agreement secures the performance, or omission, of various acts, of the kind meutioned in the last proposition, together with one or more acts, in respect of which the damages on a breach of the covenant are certain, or readily ascertainable by a jury, and there is a sum stipulated as damages, to be paid by each party to the other, for a breach of any one of the covenants, such sum is held to be a penalty of contracts, * courts are guided by the intentions of the parties in determining whether the sum contracted to be paid upon the non-performance of a covenant is to be considered as liquidated damages, to be enforced according to the terms of the agreement, or as a penalty to be controlled by an assessment of damages by a jury; and in ascertaining these intentions of the contracting parties, the ordinary rules of construction are applied. (i)1 merely." A clause in an agreement by H. to repair certain houses fur the sum of 51,500, and to have them completed fit for occupancy by December 1st, which provides, that "for each and every day's delay in the completion of said houses after December 1st, said H. shall forfeit five dollars/' is to be construed as fixiug the amount of liquidated damages, and not as a penalty. Hall v. Crowley, 5 Allen, 304.
(i) In Perkins v. Lyman, 11 Mass. 76, 81, the court said: "The question whether a sum of money mentioned in an agreement shall be considered as a penalty, and so subject to the chancery powers of this court, or as damages liquidated by the parties, is always a question of construction, on which, as in other cases where a question of the meaning of the parties in a contract provable by a written instrument, arises, the court may take some aid to themselves from circumstances extraneous to the writing. In order to determine upon the words used, there may be an inquiry into the subject-matter of the contract, the situation of the parties, the usages to which they may be understood to refer, as well as other facts and circumstances of their conduct; although their words are to be taken as proved by the writing exclusively." The fact that the amount of the damages is uncertain, and cannot easily be determined by a jury, inclines the courts to
 
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