The colored churchmen of the Diocese soon learned that in Bishop Cheshire they had a staunch friend and one from whom they could count upon receiving a fair and sympathetic hearing. He reciprocated this confidence with a like faith in them. It was a regular practice of the Bishop to attend only the first day's session of the annual meetings of the white and colored convocations. He did this in order to give the clergy an opportunity of "speaking their mind freely." He always remembered an observation of George Eliot that "the first thing the clergy do, when they get together in convocation, is to abuse the Bishop." In this connection Bishop Cheshire once remarked: "I do not know what the white clergy may do, but I do not believe my black clergy will have anything to say against me even in my absence."[49]

At the opening of the twentieth century one of the most important questions facing the Episcopal Church in the South was the separation of the Negro work in each diocese from that of the white. Bishop Cheshire was strongly opposed to any separation of the church's work founded solely on the racial feeling. He disliked to see the unity of the Diocese disrupted, and believed the ideal situation was "a church and a diocese which in its annual gatherings should represent visibly the oneness of all races and colors in Christ."[50] He realized, however, that he could not be guided entirely by his personal feelings on a question of such importance. A large body of the Negro clergy and many white churchmen throughout the South felt that the welfare of the church demanded some sort of separate organization for the colored work.

When he met his diocesan convention in the spring of 1907, Bishop Cheshire announced his position on this question. Since the colored people seemed to desire an organization of their own, he believed the time had come for the church to take some definite action. He asked the convention to make known its views on the question of separation, since it would come up for discussion in the General Convention that fall. The Bishop stated that two plans of organization for the Negroes were being considered. One provided for the consecration of suffragan bishops who should have charge of the colored clergy and laity and should be under the diocesan bishop. The other called for the consecration of missionary bishops who should have charge of the colored work in contiguous dioceses and who should be responsible to the General Convention. The Bishop declared that he was heartily in favor of the latter plan, believing that it met the needs of existing conditions much more justly and adequately than the former. Moreover, the colored people themselves seemed to favor the plan of using missionary bishops. If they were used they would be under the direct control of the General Convention and would be given more independence than suffragan bishops, who would be under the administrative jurisdiction of the white diocesan bishop. Bishop Cheshire felt that if the colored work was to be made independent of the white, the Negro bishops should be given some administrative as well as spiritual responsibilities.

When the convention took up the question of the colored work, it referred the whole matter to a special committee. After careful study, the committee recommended that the Negroes be given a separate organization, that the plan of missionary bishops be adopted, and that the deputies from the Diocese should present these recommendations to the General Convention. The committee's report was adopted.

At the General Convention, which met in the fall of 1907, the Conference of Church Workers among Colored People presented a memorial in which it advocated a separate organization for the Negroes and the election of suffragan bishops. A joint committee of the House of Bishops and the House of Deputies, of which Bishop Cheshire was made a member, was appointed to consider the memorial. This committee recommended the adoption of the principal features of the memorial. Bishop Cheshire and one other member of the committee presented a minority report in which they urged the use of missionary bishops. Their report was defeated in the House of Bishops by a vote of fifty to thirty-four, while that of the majority was carried, forty-five to thirty-three. After the defeat of his proposal, Bishop Cheshire voted for the majority's report, believing it preferable to no action on the subject.

The question of the racial episcopate was, however, far from being settled. During the next three meetings of the General Convention Bishop Cheshire and a few others continued to work for the adoption of the plan of missionary bishops. In 1913 they succeeded in getting the plan approved by the House of Bishops, but it was defeated by the House of Deputies. The southern bishops and clergy were the most undecided as to what plan they wanted to put into effect. Up to 1918 the Diocese of North Carolina had taken no action towards electing a suffragan bishop for the colored work. In 1917 Bishop Cheshire advised his diocesan convention to consider the question. The next year the convention voted to proceed to the election of a suffragan bishop.

Before nominations for the office were called for, Bishop Cheshire gathered together the colored clergy and laity of the convention for an informal discussion. He told them that, in his opinion, Rev. Henry B. Delany, who was then archdeacon of the colored convocation, was the best man for the office. Rev. M. A. Barber strongly represented the qualifications of the Rev. Mr. Baskerville, who had been recommended by Bishop Guerry, of South Carolina. Mr. Delany then withdrew from the conference, and Bishop Cheshire asked the colored clergy to express themselves frankly on their preference. Every one of them expressed the opinion that, while they thought Baskerville was an excellent man, they did not think he could compare with Delany in qualifications for the office of bishop. Of this unanimity of opinion, Bishop Cheshire remarked: "It was something of a surprise to me—for I really did not know how strong their feelings were."

When the convention proceeded to the election of a suffragan bishop, Delany was the only man nominated. He received every vote of the clergy and laity. When he was presented to the convention and asked to say a few words, he simply remarked: "I cannot speak. I cannot utter what I feel. I thank you." Bishop Cheshire characterized his laconic expression as "about the best speech he could possibly have made."[51]

Archdeacon Delany was highly esteemed by both white and colored churchmen, and his election met with general satisfaction throughout the Diocese. Bishop Guerry wrote Bishop Cheshire that he thought Delany was "the logical man and I believe you have made a wise choice.... I envy you the privilege of having been the first Diocese in the Carolinas to take the lead in so far reaching a policy."