Robert Loring Lent was assistant keeper at Sing Sing Prison when extreme punishment was the norm instead of rehabilitation. Lent's harsh and brutish exploits are detailed frequently in Isaac T. Hopper's diary. On page 130 of volume 2, Hopper recounts that prisoners have described men being knocked down as if they were oxen. Lent was specifically cited on page 159 of volume 2 as treating prisoners very harshly, knocking men down, stomping on them, kicking them, and cursing at them. 

              Robert Lent was born in Cortlandt, Westchester County, New York on August 25, 1803 to parents John Lent and Phebe Barrett. [1] He married Catherine Stratton on December 26th, 1830.[2] They had five children together: Catherine (1831-1891), Elizabeth (1834-1909), Robert (1837-1869), Esther (1841-1914), and Wells (1846-1848). [3]  The earliest known record, a Westchester Herald article, of Robert Lent working as assistant keeper in Sing Sing prison dates to 1839.[4] However, Lent self-dated his start at Sing Sing to be around 1834. He also stated that he had been engaged as architect of the prison between January 1848 and March 1852.[5] Working in the Sing Sing Prison appears to have been a Lent family business, as Robert’s brothers Paul [6] and John[7] were employed there as well.

              Robert Lent and A.H. Wells worked together at Sing Sing for a time according to Isaac T. Hopper’s diary. The two men knew each other as early as 1838, when they were both elected town officers of Ossining; Lent as Vice President and Wells as Secretary.[8] The two men were notorious within the prison for senselessly beating inmates at Sing Sing, [9] especially during Hopper’s diary entries of the late 1840s and early 1850s. For example, on page 152 of volume 2 of the diary, Hopper remarks that prisoners have mentioned that “Wells the Warden…is altogether under the influence of Lent”. This suggests that Robert Lent held the most power in Sing Sing prison. This is not a comforting thought, especially when one considers Hopper’s entry on page 167 of volume 2, which describes Lent as not having “human feelings” and was “not fit to be a keeper”, and his entry on page 334 of volume 2 that describes him as an "inhuman monster".

              In his later years, Lent lived a far quieter life as a farmer in Yorktown, which is located within the same county as the town of Sing Sing.[10][11] He died on May 17, 1877 at the age of 73 years.[12]

[1] Nelson Burton Lent, History of the Lent (van Lent) Family in the United States 1638 - 1902 (Newburgh, NY: Newburgh Journal Printing House and Book-Bindery, 1903), 114, https://babel.hathitrust.org/cgi/pt?id=loc.ark:/13960/t78s4sq31;view=2up;seq=6;size=150.

[2] Westchester Herald (Ossining, New York), January 4, 1831: 3. Readex: America's Historical Newspapers. https://infoweb.newsbank.com/apps/readex/doc?p=EANX&docref=image/v2:10CCB28D5616E070@EANX-150FF2E8EACBDB38@2389822-150FA9EB182D7FB8@2-150FA9EB182D7FB8@.

[3] Nelson Burton Lent, History of the Lent (van Lent) Family in the United States 1638 - 1902 (Newburgh, NY: Newburgh Journal Printing House and Book-Bindery, 1903), 114, https://babel.hathitrust.org/cgi/pt?id=loc.ark:/13960/t78s4sq31;view=2up;seq=6;size=150.

[4] Westchester Herald (Ossining, New York), April 23, 1839: 2. Readex: America's Historical Newspapers. https://infoweb.newsbank.com/apps/readex/doc?p=EANX&docref=image/v2:10CCB28D5616E070@EANX-1506B8EB58C67010@2392853-150678F72B381258@1-150678F72B381258@.

[5] New York (State), Documents of the Assembly of the State of New York, Seventy-Eighth Session, vol. 3, 60-80 (Albany, NY: C. Van Benthuysen, 1855), 324.

[6] Hudson River Chronicle (Ossining, New York) 2, no. 27, April 23, 1839: [2]. Readex: America's Historical Newspapers. https://infoweb.newsbank.com/apps/readex/doc?p=EANX&docref=image/v2:10DBDB164C232D80@EANX-10DAA03EB1C2A1D8@2392853-10DAA03F1494EFA8@1-10DAA040AC4D27F0@.

[7]1850 United States Census, Ossining, Westchester County, New York, digital image s.v. "John B Lent," Ancestry.com.

[8] Hudson River Chronicle (Ossining, New York) 1, no. 22, March 20, 1838: [3]. Readex: America's Historical Newspapers. https://infoweb.newsbank.com/apps/readex/doc?p=EANX&docref=image/v2:10DBDB164C232D80@EANX-10DA9E79C59C7E30@2392454-10DA9E7A63DF9800@2-10DA9E7C49C16FC0@.

[9] Heale, M. J. "The Formative Years of the New York Prison Association, 1844-1862 : A Case Study of Antebellum Reform." New-York Historical Society Quarterly 59, no. 4 (October 1975): 337.

[10] 1860 United States Census, Yorktown, Westchester County, New York, digital image s.v. "Robert Lent," Ancestry.com.

[11] 1870 United States Census, Yorktown, Westchester County, New York, digital image s.v. "Robert Lent," Ancestry.com.

[12] New York Herald (New York, New York) XLII, no. 140, May 20, 1877: 12. Readex: America's Historical Newspapers. https://infoweb.newsbank.com/apps/readex/doc?p=EANX&docref=image/v2:11A050B7B120D3F8@EANX-129A1BDCD19E3D18@2406760-129A1BE2B38CEA28@11-129A1C0C14DDC048@.