With the coming of the twentieth century, politics and the office of sheriff became universally intertwined. Grover Cleveland was an elected sheriff in Erie County, New York prior his being a district attorney, New York State Governor, and eventually president of the United States. Accounts of his term of office as sheriff identify him as a competent administrator, and the success he had in office enabled him to use it as a stepping stone to greater political heights. Al Smith, another former governor of New York State, and presidential candidate, was elected sheriff of New York City. It was under Smith's term as sheriff that the office in that jurisdiction changed drastically. In 1936, New York City Mayor LaGuardia began an intensive investigation into the elected position of sheriff in New York City. He further identified the office as a stronghold for political patronage and opportunistic abilities for "pocket lining". It was reported that Al Smith netted over $50,000 annually in salaries and fees, which was an incredibly exorbitant amount for the 1930's and early 1940's.¹⁴¹

The post enabled the sheriff to make political appointments to enhance his own political stature. Seventy-five percent of the sheriff's 360 appointments went to party committeemen. The remaining twenty-five percent had to convince party leaders of future loyalty before they were recommended for placement. The office of New York City Sheriff allowed the dominant political party to reward allegiant members with employment at taxpayer expense. Al Smith would later testify before the LaGuardia Commission that the job of sheriff was not only financially lucrative but required very little effort. According to Smith:

"I was sheriff myself and I was busy looking for something to do and, if it had not been for the impending war and the time I put into selling liberty bonds and war saving stamps and seeing the boys off, I would have nothing to do".¹⁴²

This abuse of the office prompted numerous civic groups to take action. The "League of Women Voters", accumulated 90,000 legitimate signatures which forced an amendment to the city charter to establish a single sheriff for the five counties within the greater New York City area. Further, the amendment would require that the sheriff be selected from a civil service list. In 1941, the amendment passed and 355 potential candidates took the examination. On January 1, 1942, John L. McCloskey, a lawyer serving as deputy commissioner of the city department of investigation, was appointed to the position as the first civil service sheriff of New York City. The office was re-staffed with employee appointments from competitive civil service lists. Undersheriffs were appointed by the sheriff to direct each of the five local county offices. Examinations for undersheriff and chief deputies were limited to members of the local bar association, thereby limiting the senior jobs to experienced lawyers with distinguished educational pedigrees.¹⁴³

The responsibility of operating jails and transporting prisoners was deleted from the sheriff's capacity and the functions were transferred to the New York City Department of Corrections. The sheriff's office was relegated to matters of civil enforcement. The salaries of the employees were brought to a realistic amount without the benefit of fees. The office of the New York City Sheriff became exclusive and unique in its formation. No other sheriff's department in the country operates in this manner.¹⁴⁴

As an elected official, the sheriff often times is more subject to popular will than an appointed police chief. Along those lines, from a professional police management perspective, the elected nature of the sheriff's office has presented problems indigenous to its own perspective. For instance: sheriffs with no law enforcement service or training have been elected to the position, sheriffs lacking skills have defeated sheriffs with greater skills by virtue of political popularity, there have been no statutory experience or education requirements placed on seeking the job, and survival in office has sometimes required political compromise at the expense of professional commitment.¹⁴⁵