Ira Couch's Last Will and Testament, filed in 1855, two years before his death, appears in the public record in the context of the ongoing lawsuits among family members and other parties who were arguing for his bequeathed real estate holdings. According to the will, Ira's widow, his brother James, and his appointed trustee and brother-in-law, William H. Wood, would retain control of his land and properties for twenty years. After twenty years in trust, the estate was to be divided into four parts, shared equally between his widow Caroline, his daugher, Caroline, his brother James, and his James's son, Ira.

By 1877, the twenty-year point in the will, the Couch estate had dwindled to the point that James Couch held substantial debts. The 1871 Chicago Fire destroyed the Tremont House and all of the property on the estate's other land holdings. Although the Tremont House was rebuilt along with buildings on the other properties, financial troubles plagued James throughout this period, and into the next decade.

Ira Couch's legacy and worth were connected to his real estate holdings. Although his estate was valued at more than one million dollars at the time of his death, the money was tied-up in his properties. His debts, which were also great were paid with mortgages on his properties. The trustees of his estate were instructed to manage his real estate holdings for twenty years, after which time, they were to divide his legacy four-ways.

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The year 1877 is significant in the Chicago City Cemetery timeline too.
A February 18, 1877 Chicago Tribune article details the progress of transforming the grounds at the southern edge of Lincoln Park. The Couch Tomb is mentioned as being the last remaining vestige of the graveyard. If families did not remove their loved ones from the City Cemetery grounds, the responsibility fell to the cash-strapped Lincoln Park Commissioners. According to the newspaper article the cost would be $3000. to remove the vault to Rosehill Cemetery. The article states: "... the Commissioners have determined to let it remain, planting trees thickly around it."

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See the entire Supreme Court case here.

"First. I do hereby give, bequeath, and devise unto my beloved wife, Caroline Elizabeth Couch, and my brother, James Couch, and my brother-in-law, William H. Wood, whom I hereby constitute, make, and appoint to be my executrix, executors, and trustees of this my last will and testament, and the survivors of them, and, in the event of the death of either of them, the successor appointed by the surviving trustee or trustees, all my estate, both real and personal, of every nature and description, for the term of twenty years, in trust, and for the uses and objects and purposes hereinafter mentioned and expressed, and for the purpose of enabling them more fully to carry into effect the provisions of this will, and for no other use, purpose, or object, hereby giving and granting unto my said executors and trustees full power and lawful authority to lease my real estate at such time or times, and in such parcels, and in such way and manner, and upon such terms and conditions as to my said executors and trustees, or the survivors or successors of them, in their sound discretion, shall be deemed most advantageous and for the true interest of my estate, but no lease shall be granted of any building for a longer term than five years, and all leases shall expire at the end of twenty years from the time of my death. And I do also hereby authorize and empower my said executors and trustees, and the survivor or survivors of them, and their successors, from time to time, as they, in the exercise of a sound discretion, shall deem for the true interest of the estate, to purchase with the surplus funds belonging to my estate such real estate as they may deem proper and expedient, and take and hold the same, as such executors and trustees as aforesaid, upon the same trusts, and for the same uses and purposes, as the other real estate now owned by me, and more especially to purchase for the benefit and use of my estate, when they, my said executors and trustees, or the survivors and survivor of them, or successors, shall think it expedient so to do, any real estate which is or may be subject to any such judgment, decree, or mortgage as is or at any time hereafter may become a lien, charge, or encumbrance for my benefit, or for the benefit of my heirs or executors, upon the same, and, again, that my said executors and trustees have the like discretion to lease the same. And I do hereby authorize my said executors and trustees, if they shall think proper so to do, to loan on real estate situate in the City of Chicago any of the surplus moneys arising from my said estate, as aforesaid, on bond and mortgage: provided always that such real estate shall be worth double the amount so loaned thereon, over and above any other liens and encumbrances existing against the same, and that such moneys shall not be loaned for a longer period than twenty years from my decease."

"And, generally, I do hereby fully authorize and empower my said executors and trustees, from time to time, to improve my real estate, and invest all surplus moneys belonging to my estate, arising from any source whatever, and not wanted immediately, or required to meet the payments and advances, legacies, annuities, and charges required to be made under this, my said will, in such way and manner as to them, my said executors and trustees, or the servivor or successors of them, in the exercise of a sound discretion, shall be deemed most safe and productive; but no moneys are to be invested except in improving my real estate, or in the purchase of other real estate, or on bond and mortgage as aforesaid. And I direct that my executors or trustees, or their successors, shall not purchase or improve by building upon any real estate after the expiration of sixteen years from my decease."

"Relying on the fidelity and prudence of my said executors and trustees in executing the various trusts to them given and confided in and by this, my last will and testament, my executors are authorized to mortgage my real estate to improve by building on the same only in the event of the destruction of some of my buildings by the elements, and then only to supply other buildings in the place of those destroyed."

"It is my will that all my just debts and the charges of funeral expenses be paid and discharged by my executors, as hereinafter named and appointed, out of my estate, as soon as conveniently may be after my decease, and the said debts become due, and I leave the charge of my funeral expenses to the discretion of my said executors."

"Second. I give, devise, and bequeath to my beloved wife, Caroline Elizabeth Couch, after the expiration of the trust estate vested in my executors and trustees for the term of twenty years after my decease, one-fourth part of all my estate, both real and personal, after the payment of all my debts, funeral expenses and the legacies in this will mentioned, which are hereby made a charge on said real estate, which part is to be accepted by my said wife and received by her in lieu of dower."

"Third. I give, devise, and bequeath unto my beloved daughter, Caroline Elizabeth Couch, after the expiration of the trust estate so vested as aforesaid, one-fourth part of all my estate, both real and personal, after the payment of all my debts, funeral expenses, and the legacies in this will mentioned."

"Fourth. I give, devise, and bequeath unto my brother, James Couch, after the expiration of the trust estate so vested as aforesaid, one-fourth part of all my estate, both real and personal, after the payment of all my debts, funeral expenses, and the legacies in this will mentioned."

"Fifth. I give, devise, and bequeath unto my nephew, Ira Couch, son of my brother, James, after the expiration of the trust estate so vested as aforesaid, the remaining one-fourth part of all my estate, both real and personal, after the payment of all my just debts, funeral expenses, and the legacies in this will mentioned."

"Sixth. I hereby will and direct that the said legacies hereinafter mentioned shall be charged on my real estate, to be paid out of the rents and profits thereof as hereinafter directed."

(from an 1891 Supreme Court document (141 U.S. 296), "By the seventh and eighth clauses, the testator gave annuities for life to his sister Rachel and to his mother-in-law; and by the ninth clause an annuity to a brother-in-law who died before him.)

"Tenth. I give and bequeath to my wife, Caroline Elizabeth Couch, for the support of herself and daughter, from the rents of my real estate, the sum of ten thousand dollars a year until all the debts due by me are paid by my executors, and after my executors have paid such debts I give and bequeath to her for the same purpose fifteen thousand dollars a year, to be paid quarterly to her until my daughter becomes of age or is married, when my daughter may draw one-fourth of all the net rents and profits, after payment of all expenses, taxes, repairs, legacies, annuities, and other charges on my said estate, and my wife may draw ten thousand dollars a year until my nephew, Ira Couch, attains his majority, when she shall draw one-fourth of all the net rents and profits, after paying all expenses, taxes, repairs, legacies, annuities, and other charges as aforesaid."

"Eleventh. I give and bequeath to my brother, James Couch, for the support of himself and family, from the rents of my real estate, the sum of ten thousand dollars a year, to be paid quarterly until all the debts due by me are paid by my executors, and after such debts due by me are paid, I give to him for the same purpose fifteen thousand dollars a year, to be paid quarterly to him until my nephew, Ira Couch, attains his majority, after which time I give to my brother, James Couch, one-fourth part of all the net rents, income, and profits of my estate, to be paid him by my executors quarterly until the final division of my estate, which shall take place at the end of twenty years after my decease, and not sooner."

(from an 1891 Supreme Court document (141 U.S. 296), "By the twelfth and thirteenth clauses, he gave legacies to children of a deceased bother, and of his sister Rachel.)

"Sixteenth. I will and direct that no part of my estate, neither the real nor the personal, shall be sold, mortgaged (except for building), or in any manner encumbered until the end of twenty years from and after my decease, when it may be divided or sold for the purposes of making a division between my devisees as herein directed."

"Seventeenth. It is my will that any and all real estate which may hereafter be purchased by me shall be disposed of, and is hereby devised, in the same manner and to the same persons as if owned by me at the time of making this, my last will and testament."

"Eighteenth. In the event of any of the legatees or annuitants being alive at the end of twenty years after my decease, it is my will, and I hereby direct, that there shall be a division of all my estate, both real and personal at the end of said twenty years, anything herein contained to the contrary notwithstanding, and in such case my executors, in making division of the said estate, shall apportion each legacy or annuity on the estate assigned to my devisees, who are hereby charged with the payment of the same according to the apportionment of my said executors."

"Nineteenth. It is my will that my trustees aforesaid shall pay the several gifts, legacies, annuities, and charges herein to the persons named in this will, and that no creditors or assignees or purchasers shall be entitled to any part of the bounty or bounties intended to be given by me herein for the personal advantage of the persons named, and therefore it is my will that if either of the devisees or legatees named in my will shall in any way or manner cease to be personally entitled to the legacy or devise made by me for his or her benefit, the share intended for such devisee or legatee shall go to his or her children in the same manner as if such child or children had actually inherited the same, and in the event of such person or persons having no children, then to my daughter and her heirs."

"Twentieth. It is my will that the estate, both real and personal, hereby devised and bequeathed to my daughter, Caroline Elizabeth, shall be vested in trustees, to be chosen by herself and my trustees herein named, before her marriage, and said trustees shall be three in number, to whom all her estate, both real and personal, shall be conveyed at the expiration of twenty years, the time hereinbefore specified for the termination of the estate of my trustees herein, to such trustees so to be appointed as aforesaid, and it is my will that the estate, both real and personal, herein devised and bequeathed for the benefit of my daughter shall be held by such trustees for the sole and only use and benefit, and that the same shall not in any manner be subject to the marital rights of any future husband my daughter may have, and that all moneys shall be paid by such trustees to my daughter personally, and to no other person for her except upon her written order or assent, and it is my will that her said trustees pay to her during her life the entire net income of the estate, both real and personal, herein devised and bequeathed to my daughter, after the same shall have been conveyed to her trustees by my executors and trustees or their successors, and after the death of my said daughter I direct that the said estate, both real and personal, shall be conveyed to the children of my daughter, and, in the event of her having no children, to such person as my daughter may direct by her last will and testament."

"Twenty-First. It is my wish also that William H. Wood, my executor and trustee, shall be charged with, and take upon himself, the collection of all rents accruing to my estate, and that he shall continue to perform the same during the period of twenty years after my decease, and for the performance of this service and other services, and for his general care and supervision of the affairs of my estate, I hereby direct that the sum of two thousand dollars per annum shall be paid to him; but in the event of his decease before entering upon said duties, or before the twenty years aforesaid shall expire, or shall decline to act as in this section provided, I hereby authorize and direct my said trustees to appoint some other person to act in his stead in collecting said rents and performing the other duties as above specified, and to pay him the same compensation therefor which said Wood would have had."

"Twenty-Second. And in the event of the marriage of my said wife after my decease, it is my will and I hereby authorize and direct my said trustees and executors to pay over to my said wife, and to no other person, the rents, annuities, legacies, and other income herein bequeathed to my said wife, and to take her separate receipts therefor, and it is my will that my said trustees and their successors in such case hold the same, subject to her order, in trust for my said wife, so that said property so devised and bequeathed to her as aforesaid can in no event be subject to the marital rights of such husband."