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The surroundings of Captain Pinckney's building deteriorated. Coal sheds, horse stables, and manure piles led some of the members to say that they would not pay dues if the club met there any more. On January 25, 1898 (This date is based on Frank M. Whitehall's history of the club. The dates in the William Merritt history are inconsistent.) the club met in Isaiah Miller's shop and passed a motion that the club would no longer meet in the building. This led to a discussion of where they would meet. The outcome of the discussion was the idea of buying land and building a club house. The treasurer pointed out that he had paid out $15 more than he had received in the past year so the club had no money. Capt. Frank F. Collyer said that he would give the club fifty dollars if the club could raise the balance needed, obviously an early example of a challenge grant. John Constantine said he would give the club ten dollars. Steven Glass said he would lend the club ten dollars as did Isaiah Miller and D. Bradbury. B.B. Merritt said he would lend five dollars. With that settled, a committee was appointed to find if the Jackson lot could be bought and at what price. The lot was a small, three-cornered piece of property east of the present clubhouse. It was on the water, and the members thought that they could build a dock along the river edge.
The committee reported at a January 31 meeting that the price was $100. The club voted to buy the property, and the land was bought from Caroline A. Jackson for the sum of $100. The building of the dock was discussed at a February 8 meeting. Again the problem of finding financing had to be overcome. There was a little money from dues in the treasury, and Isaiah Miller said he would lend $40 to the club to help pay for the timber. It was also agreed that members who worked on the dock would be paid 15 cents per hour worked when the club's finances improved. Early in the spring the dock was built and was ready to receive a building.
William Merritt then drew up plans for a clubhouse. The proposed building was two stories high, sixty feet long and twenty-two feet wide, with four rooms upstairs, consisting of a dressing room, a kitchen, a smoking room, and a reception room about the size of the meeting room in the 1995 clubhouse. The lower floor was for storing ice boats in the summer and holding entertainments in the winter. When the plans were submitted to the club, it was unanimously agreed that the members would build the clubhouse under the same conditions as the dock.
Financing the purchase of the materials was a problem. For one thing, the club was in debt in the amount of $200. A committee was appointed at the December 3, 1898 meeting to try to borrow $1,000. It is obvious that the provision in the 1890 constitution and by-laws that the club could not go into debt for more than $100 was no longer in effect. Indeed, the provision is missing from the 1903 version.
The committee went to lawyer George Wood, a member of the club, for advice. He arranged for a note payable to Annie Cornell. F.F.Collyer, I. Miller, C. Merrittt, William Merritt, S.S. Glass, T. Smith, J. Mullahy, and John Constantine signed the note, and Mr. Wood handed over a check for $1,000.
The members then set about building the clubhouse. William Merritt kept the time books, received all moneys, and paid all bills. He, Stephen Glass, John Sturges, B. Merritt, I. Miller, C. Merritt, S.S.Meade, and J. Montague did all the work for fifteen cents per hour. The clubhouse is shown in a February 1902 photograph. (The corresponding slide is marked "O.")
At about April, 1899 Ms. Cornell asked for her money back. George Wood arranged for another note for $800 signed again by various club members. The proceeds with $200 that the club had in hand were used to pay Ms. Cornell. Finally, at a meeting of December 29, 1899 (This date is different from the 1890 given in William Merritt's history. The sequence of other dates makes it plausible that 1890 is a typograhical error.), the following resolution was passed: "Whereas F.F. Collyer, S.S. Glass, D. Bradbury, B.B. Merritt, T. Smith, I. Miller, C. Merritt, S.S. Meadee, J. Mullahy, J. Constantine, J.S. Ackerman, and William Merritt have borrowed eight hundred dollars for the use of this club, be it resolved that the club authorize the trustees to issue a note to said parties for eight hundred dollars payable one year after date with interest at 5% payable semi-annually."
However, this was not enough to pay for the clubhouse. At a meeting of February 26, 1901 a motion was passed to borrow $450 to pay off all debts except the outstanding note. The Merchants National Bank of Poughkeepsie issued a demand note for the sum at 5% interest.
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