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Gabriel Lilly was an overseer at Monticello from 1800 to 1805. Great George, the previous overseer, died on November 2, 1799, so it is possible he was hired soon after George's death. He had responsibility for the nailmaking operation and for supervising enslaved men working at non-agricultural tasks such as digging of the canal for the Shadwell mills, the Ice House, and the construction of the Shadwell toll mill. He had very little to do in the way of agricultural management, since Jefferson leased out the farm fields to John Craven.
Lilly treated the slaves poorly by whipping them excessively. By 1805, he asked for a raise and moved to Kentucky.
Primary Source References
1800. "Lilly" noted as Monticello overseer 1800 to 1805.
1800 December 22. (Richard Richardson to Jefferson). "I Carryed Mr. Lilley to the Shop this morning and told the Boys they was to Be under his direction and Joe to say when their nails was made too Big or too small with this arangement [sic] they will go on, till I see Mr. powel or hear wheather [sic] he is a Comeing [sic], if he does not I will return directly after Christmas..."
1801 January 3. (Thomas Mann Randolph to Jefferson). "Lillie has failed in hiring, except one single labourer; they could not be had under 25. L. any where and difficultly for that: his exertions were what might have been expected of him but the great price in our neighborhood and the impossibility of persuading them to come up from below, which the facility of hiring everywhere makes allways [sic] a condition, have rendered them vain...Having abandoned all hope of Lillies hiring hands I directed him to take the lads from the shop, leaving three full fires of the boys with Burwell at their head...I have directed Lillie to look himself to those who remain at the nailery, for their work...It was absolutely necessary to do something without waiting to consult you for the Nailery was all in confusion, Lillie without a hand and Craven in despair because the work to be done for him was standing still." .
1801 January 16. (Jefferson to Martha Jefferson Randolph). "It gave me great joy to learn that Lilly had got a recruit of hands from Mr. Allen, tho' still I would not have that prevent the taking all from the nailery who are able to cut, as I desired in mine of the 9th, as I wish Craven's ground to be got ready for him without any delay."
1801 January 23. (Jefferson to Thomas Mann Randolph). "I forgot to ask the favor of you to speak to Lilly as to the treatment of the nailers. It would destroy their value in my estimation to degrade them in their own eyes by the whip, this therefore must not be resorted to but in extremities. As they will be again under my government, I would chuse they should retain the stimulus of character. After Lilly shall have compleated [sic] the clearing necessary for this year for Mr. Craven, I would have him go on with what will be wanting for him the next year...P.S. when I come home I shall lay off the canal, if Lilly's gang can undertake it. I had directed Lilly to make a dividing fence between Craven's fields at Monticello and those I retain...I hope Lilly keeps the small nailers engaged so as to supply our customers in the neighborhood, so that we may not lose them during this interregnum."
1801 January 29. (Jefferson to Thomas Mann Randolph). "I am very glad indeed, to find that Lilly has got so strong a gang, independent of yours and the nailers...I should be glad [if] Mr. Lilly or Mr. Dinsmore would count the faggots on hand, and inform me of the quantity by return of post, as I have forgotten the state of the supplies on hand when I left home."
1801 June 13. (Thomas Mann Randolph to Jefferson). "Lillie has begun to work on the Canal and was going on with much spirit but has been compelled by [[John Craven|Craven's]] discontent to return to the new clearing to collect and burn every scattered chunk and grub up every neglected bush in it, altho it was already done in a manner much better than usual."
1801 July 16. (Jefferson to Martha Jefferson Randolph). "...the inclosed letter to mr Craven...will secure you all the resources for the house which he can supply...Lilly has before received orders to furnish what he can as if I were there."
1802 January 17. (Jefferson to Martha Jefferson Randolph). "P.S. in my last week's letter to Mr. Randolph I inclosed one for Mr Lilly with 940.D. in it, which I shall be glad to hear got safe to hand."
1802 April 3. (Jefferson to [[Martha Jefferson Randolph]]). "I have desired Lilly to make the usual provision of necessaries for me at Monticello, and if he should be at a loss for the particulars to consult with you."
1802 September 28. (Jefferson to Martha Jefferson Randolph). "He is to come over, designate to Mr. Lilly and Mr. Hope the spot where my small mill is to be built, so as not to be in the way of the large one...In the spring he is to designate to Mr. Lilly and Mr. Hope the spot for the large mill."
1803 January 27. (Jefferson to Martha Jefferson Randolph). "I find Mr. Lilly was to begin filling his icehouse the 21st. We have had no thaw here since that till yesterday, and the river is still entirely blocked up; so that if the weather has corresponded there, I am in hopes he will have got his house full."
1803 February 7. "Inclosed to Gabriel Lilly for waggonage of ice 30.D..."
1803 March 25. (Jefferson to James Walker). "I find it the opinion of Mr. Lilly that having hired extraordinary forces for the year he shall be able to compleat [sic] the canal for my mill this summer...I will therefore ask of you to come over without delay and mark out the site of both. If you come before Tuesday I shall be at home. If afterwards apply to Mr. Lilly my [overseer] who will send for Mr. Hope and both of them will attend you on the ground."
1803 April 24. (Jefferson to George Jefferson). "Will you be so good as to procure from old Mr. Collins or any other faithful seedsman 1. gallon of earliest Frame peas and 2. gallons of Dwarf Marrowfats and send them addressed to Gabriel Lilly at Monticello."
1803 June 8. (Jefferson to Thomas Mann Randolph). "There are generally negro purchasers from Georgia passing about the state, to one of whom I would rather he [slave Cary] should be sold than to any other person. I should regard price but little in comparison with so distant an exile of him as to cut him off compleatly [sic] from ever again being heard of. I have written this to Mr. Lilly and will thank you to advise and aid him in procuring a sale...I should indeed be glad to have my toll mill up a season before another, merely to learn people the way to it...but this I am in hopes Lilly will enable me to effect..."
1803 September 21. "Settled with Gabriel Lilly and paid him L3-17-3, being the balance due him. But this does not include his wages of the present year which are L50. and L10. extra for overlooking the nailery. From the commencement of the ensuing year he is to have 2. percent of all nails sold instead of the L10."
1803 November 27. (Jefferson to Mary Jefferson Eppes). "Mr. Lillie having finished the mill, is now I suppose engaged in the roadprobably the East Road to the Shadwell ford. which we have been so long wanting, and that done, the next job will be the levelling of Pantops."
1803 December 24. (Thomas Mann Randolph to Jefferson). "Some say neither of these elevations [in the canal bottom] extends farther than four or five yards: Lillie believes not more than 10 or 12 feet...The wheel has been set in motion today and moved with great velocity when four inches covered. Lillie was determined to grind some grain before night."
1804 January 14. (Martha Jefferson Randolph to Jefferson). "Lilly has been here [Edgehill] to advise with me about Kit. He is now in Charlottesville jail where he passed himself for a negro of Mr. Randolph's, Lilly is afraid to take him out for fear fo his going off again. He thinks you wished him sold and the money laid out in another, but he says his head was so confused during and for some time after his illness that he cannot recollect whether you gave him any orders to that effect or not: the result of the conversation however was that if he could get 120 or L25 before he could hear from you he should sell him rather than miss the sail but that the would be much obliged to you to let him know by the next post what you wish done with him in case of his not having been able to dispose of him."
1804 January 28. (Jefferson to James Walker). "I must therefore get you to lay off the exact spot for the millhouse for Mr. Hope, furnish him with a plan, and give Mr. Lilly a bill of scantling which he will have sawed at the sawmill if compleated [sic]. I presume the sooner the ground is laid off the better, that Mr. Lilly may commence digging the foundation. Possibly he may find blowing to do in it. You can also be so good then when you are there as to advise him about the canal, which has not yet been properly compleated [sic] and the wing dam."
1804 February 26. (Jefferson to Mary Jefferson Eppes). "Will you desire your sister to send for Mr. Lilly and advise him what order to give Goliath for providing those vegetables which may come into use for the months of April, August, and September."
1804 November 30. (Martha Jefferson Randolph to Jefferson). "Lilly was here Edgehill a fortnight ago to beg I would write you immediately about some business of his...He says you desired him to part with 100 barrils [sic] of corn as more than you required, but he says he has got it on very good terms 16 and 16.6 a barril [sic] and that there is not one bushell to much, on account of the heavy hauling he has to do. He says if the horses are not highly fed they will not be able to do the work...After receiving your letter he went to see Moran about the double payment that had been made, he pretended he knew nothing about it but that he would see Irving and it should be rectified, and that Lilly should hear from him in a fortnight...He is obliged to give up L. Smith's negro's tomorrow as he wished to get all the work possible out of them before they went. He defered [sic] going after Irving till their time was out, when he will immediately see him. The man that run away the first of August has never been recovered. He begged me also to speak particularly about John. He is utterly averse to the idea of having any thing to say to him another year. His conduct is such that there can be nothing like honesty or subordination where he is. His wish is that he should be sent off the plantation and indeed the instances of depravity that he mentioned in him, his art in throwing every thing into confusion, encouraging the hands to rebellion and idleness and then telling upon them so as to put Lilly out of his senses allmost [sic], are beyond conception. He says that John has frequently created such confusion by his art as to render it impossible to punish the very hands of whom he complained most, and pieces of ill will and mischief to himself inumerable, such as cutting up his garden destroying his things and once he suspects him of having attempted to poison him. He thinks it necessary for him be be allways [sic] upon his guard against his malice...Lilly's business has taken up so much of my time and paper that I have only room to subscribe my self with inexpressible tenderness."
1805 June 5. (Jefferson to Thomas Mann Randolph). "I received a letter yesterday from Lilly which gives me great desquietude. He has hitherto been on wages of L50. and L10. additional for the nailery. He writes me that he cannot stay after the present year for less than L100. Certainly I can never get a man who fulfills my purposes better than he does: and if a moderate advance as from 60. to L75. would have sufficed, I would have given it. But to L100. is a larger jump than I am willing to take if I can find another who will answer my purposes. Do you know, or can you recollect one who would, and who could be got on Lilly's present allowance? I do not wish the least intimation of this matter to any mortal; and shall withold answering Lilly till I hear from you."
1805 June 5. (Jefferson to John Strode). "The person [Lilly] whom I have there at present is at the wages of L60 and the ordinary allowances of pork and corn for his family. He is as good a one as can be. But I yesterday received notice from him that unless I would raise his wages to L100. he could remain only this year. This is so great a jump, that if I can get another worthy of confidence, I think to do so."
1805 June 16. (Thomas Mann Randolph to Jefferson). "Lillie has so much understanding activity and perseverance that he could superintend the culture of one in the best manner with the aid of his wifes son who lives with him and at the same time manage the nailery and direct any hired force you might chuse to employ for jobs to as much advantage at present. So doing he would earn his present wages and deserve a liberal share of what he made besides." 
1805 August 21. "Bought a negro woman Lucretia James' wife, her 2. sons John & Randall and the child of which she is pregnant, when born, for L180. of which L100 to be paid before his [Lilly] departure & the residue a twelve month hence."
1805 October 6. (Jefferson to Daniel Bradley). "My informant says he [runaway slave James Hubbard] confessed at once to the truth of his case, that he had three passes which he said had been given him by the son of Mr. Lilly my manager...It would be important for me to receive the passes immediately because Mr. Lilly sets out on Thursday for Kentucky, and if he can get the passes into his hands before he goes I am sure he will probe the forgery to the bottom."
1805 November 14. (Jefferson to George Jefferson). "Mr. Freeman my manager at Monticello in the place of Lilly, being new in the business, has improperly applied to you for nail rods."
1806 Fall. (Jefferson's Memorandum to Edmund Bacon). "I allow them [slaves] a best striped blanket every three years. Mr. Lilly had failed in this; but the last year Mr. Freeman gave blankets to one-third of them."
1806 May 24. "Recd. by T.M. Randolph from Gabriel Lilly 1.375 the balance due me at his departure."
1806 June 28. (Jefferson to John Holmes Freeman). "I have received an account from Mr. Higginbotham, by which I find that Mr. Lilly has left me a heavy sum for dealing to be paid there. This will render it indispensably necessary to push the nailery with all possible force."
1. This articles is based on a Monticello Research Report, n.d.
2. Please note that this list should not be considered comprehensive.
3. Edwin M. Betts, ed. Thomas Jefferson's Garden Book, 1766-1824: With Relevant Extracts from His Other Writings (1944. Rep. 1999), 56. Manuscript and transcription available online.
5. Ibid, 32:341.
6. Ibid, 32:390-391
7. Ibid, 32:475.
8. Ibid, 32:499-500.
9. Ibid, 32: 517.
10. Ibid, 33:570.
11. Ibid, 34:327.
12. Ibid, 34:580.
13. Ibid, 34:639.
14. Edwin M. Betts, ed., Thomas Jefferson's Farm Book: With Commentary and Relevant Extracts from Other Writings (Princeton: Princeton University Press, 1953. Rep. 1976, 1987, 1999), 153. Manuscript and transcription available online.
15. Ibid, 216.
17. Edwin M. Betts and James Bear, Jr., eds, Family Letters of Thomas Jefferson (Columbia, MO: University of Missouri Press, 1966, Reprinted Charlottesville: Thomas Jefferson Memorial Foundation, 1986), 222.
20. James A. Bear, Jr., and Lucia C. Stanton, eds., Jefferson's Memorandum Books: Accounts, with Legal Records and Miscellany, 1767-1826 (Princeton, NJ: Princeton University Press, 1997), 2:1092.
36. Ibid, 445.
37. Ibid, 25.