In his capacity as trustee representing the state of Illinois, Ray signed a resolution on October 19, 1857 authorizing the payment of $40,000 to Leavitt for services rendered in securing the loan for the canal. Ray wrote to Swift on October 20 to inform him that he prepared the resolution, and four days later Swift received the resolution from Leavitt. Swift promptly returned the resolution, unsigned, to Leavitt along with a written protest. In his protest, Swift argued that Leavitt had not in fact negotiated the loan, but that $640,000 had already been subscribed before Leavitt arrived in London to assist in securing funds. Swift also pointed to the fact that previous Illinois governors as well as all previous holders of Ray’s position of trustee representing the state had rejected Leavitt’s claim. According to Swift, in 1849 Leavitt had relinquished his claim to this commission as a condition of his reelection to the Board of Trustees. In that same year Leavitt reportedly agreed to arbitration on the matter by Joshua Bates, a partner in Baring Brothers & Company, who declared that Leavitt had no claim. Leavitt signed Ray’s resolution himself on October 25, 1857, and as he and Ray argued that their signatures constituted the approval of a majority of the three person Board of Trustees, he charged the $40,000 to his treasurer’s report for 1857.

The second section of the 1845 supplemental act specifies how canal trustees are to be elected, and states that “The majority of the said board of trustees shall have power and authority to act and decide in all cases, and their acts shall bind all parties”. Leavitt maintained that he and Ray constituted a majority of the three-person Board of Trustees and that with both of their votes of approval, Ray’s resolution to pay Leavitt the $40,000 had thus passed despite Swift’s dissent.

The fifth section of the supplemental act stipulates that “The preliminary expenses of the negotiation of said contract with the expenses of the examinations of the canal property by the agents appointed by the authority of the bond-holders shall be first paid by the said trustees unless some other provision for their payment be made by the General Assembly.” Swift claimed in his protest that Leavitt had received the sum of $1,266.67 in 1846 to cover his expenses in traveling to Europe in relation to the canal loan, and that this amount constituted a portion of the preliminary expenses related to the negotiation.

Buchanan had long desired the United States’ acquisition of Cuba from Spain. In his second annual message in December 1858, he laid out a case to the U.S. Congress for acquiring Cuba. A proposal in Congress to negotiate for the purchase of Cuba was introduced early in 1859, but was defeated by Republicans opposed to the admission of Cuba to the United States as a territory where slavery was legal. Buchanan continued to propose purchasing Cuba in his subsequent annual messages but lacked sufficient Congressional support for the issue. Douglas had also been a longtime proponent of the annexation of Cuba, and the issue had the potential to bring together proslavery Buchanan Democrats and popular sovereignty Douglas Democrats. In a letter to Lincoln in April of 1858, Ray reported being approached by a Douglas supporter over the possibility of Douglas opposing any Buchanan administration action on Cuba in exchange for Republican support as an anti-Lecompton candidate for the U.S. House of Representatives in the election of 1858.