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State of Tennessee
Madison County
This indenture, made at Jackson Tenn this 10th day of January 1866 between Lt. Samuel Evans for and in behalf of Billy Cunningham a freed colored orphan, now 9 years of age; of one part, and Mrs. E F Cunningham a planter of Madison county Tenn of the other, witnesseth: 
That the said LT. Samuel Evans Superintendent R.F. & A. L., does bind out and apprentice to the said E F Cunningham the said orphan Billy Cunningham to be taught to labor and perform such work as is customary on a farm or plantation, and to live with and serve the said Mrs. Cunningham as an apprentice from the date hereof till the said orphan shall arrive at the age of 21 years; during all of which time the said orphan through his lawful guardian the said Lt. Evans doth covenant with the said Mrs. Cunningham to demean himself well and faithfully as an apprentice, obeying fully the commands of the said Mrs. Cunningham or his lawful agent, and in all respects to behave himself as a faithful apprentice; neither neglecting nor leaving his business without the permission of the said Mrs. Cunningham
And for and in consideration of the service faithfully performed as aforesaid by the said orphan the said Mrs. Cunningham of the second part, doth covenant and agree to instruct, or cause to be instructed, the said orphan in the art or business of a laborer or farmer, and also to read and write the English language and to cipher as far as the rule of three; and also to provide and furnish the said orphan with comfortable clothing, wholesome food and drink and all other necessaries in sickness and health; and also, at the expiration of the term of service to allow and give said orphan the sum of seventy five dollars in current money and one new suit of clothes; and the said Mrs. Cunningham agrees that the said orphan shall not be removed out of the state in which he is bound without the consent of his guardian.
It is further agreed by the contracting parties that if, on complaint to the guardian, it shall appear that said orphan or apprentice is ill used or not taught as provided for above, said guardian shall remove and bind said orphan to such other person as he shall deem fit.
And for the faithful observance of the aforesaid obligations on the part of Mrs. Cunningham of the second part, he, the said and  surety D J Cunningham acknowledge themselves, their heirs, executors, etc., held and bound unto the said Lt. Samuel Evans for the use of said orphan in the sum of one thousand dollars.