With the 2008 presidential election season unfolding, it’s interesting to look at the backgrounds of the candidates running. For as long as anyone can remember, the men (and for the first time ever, one woman) seeking the nations highest office have been DC insiders or former governors or senators.  But now let’s go back more than 100 years, to a different era.  In a period of less than ten years, there were two presidents who, at one time in their professional careers, were law enforcement officers.

The first was the twenty second president, Stephen Grover Cleveland.  The only president to serve two non-consecutive terms, Cleveland was defeated for re-election in 1888 by Benjamin Harrison against whom he ran again in 1892 and won a second term.  A career Democrat, Grover Cleveland began his professional career in January 1863 as a deputy DA for Erie County New York.  Later that year, Congress passed the Conscription Act of 1863 which required able-bodied men to serve in the army if called upon.  A draft notice arrived shortly thereafter and Cleveland took advantage of a provision in the law that allowed him to hire someone to take his place.  Cleveland promptly paid a thirty two year old Polish immigrant named George Benninsky $150 to go off and fight in the Civil War.

In 1865 Cleveland ran for the office of District Attorney.  He narrowly lost the election to his friend and roommate, Republican Lyman K. Bass. 

Cleveland practiced law until 1870 when he found himself elected sheriff of Erie County by 303 votes.  He took office in January 1871.  The new career took him away from the practice of law but the rewards were incredible.  A salary of twenty thousand dollars per year!

In September of 1872, Sheriff Cleveland was faced with a moral dilemma.  Condemned murder Patrick Morrissey was sent to be hung but Cleveland had issues with capital punishment.  As the top lawman in the county, Cleveland could have washed his hands of the affair by paying a deputy $10 to perform the duty.  By the time the issue came around, Cleveland had already demonstrated he was not the type of sheriff to delegate the less desirable duties to someone else and he chose to handle the matter himself.  By the end of the year, Cleveland had personally hung not only Morrissey but also Jack Gaffney, a well-known gambler who had been found guilty of shooting a man over a card game.

Upon completion of his term as Sheriff, Cleveland returned to his law practice in Buffalo New York.  Many predicted that he was through with politics, as he had been regarded as too much of a non-partisan, frequently clashing with the old line Democrats.

They were wrong. 

In 1881, Cleveland was elected Mayor of Buffalo and a year later became the Governor of New York State.  He was recognized for his stance against corruption and credited with the slogan, "public office is public trust."  In 1884 he became the Democratic nominee, and was elected the 22nd President of the United States.  Having been unsuccessful in his presidential reelection bid in 1888, Cleveland reemerged successfully in his third campaign in 1892, making him the only president in history to be reelected after a prior defeat.

Throughout his tenure he was known for his independence and controversy in his cabinet appointments, often again at odds with his political party.  He eventually retired to his home in New Jersey where he subsequently died in 1908.

Today history judges Stephen Grover Cleveland as one of the most honest men to ever serve as president even if the legacy of his accomplishments as the commander in chief isn’t well known.  Today his face is forever immortalized on the $1000 dollar bill.

The next former lawman to ascend to the White House may very well be one of the most memorable presidents in our nation’s history.

Theodore Roosevelt was a weak, asthmatic child who grew up to be one of the most robust and ambitious U.S. presidents ever.  Born on October 27, 1857, into a wealthy American family of Dutch descent, Roosevelt was related to former President Martin Van Buren as well as the cousin of future president Franklin D. Roosevelt.  His father was a merchant and banker.  His mother was a descendant of Robert III, King of the Scots.

As a young boy, Roosevelt worked hard to improve his health through vigorous exercise of both mind and body.  By age nine “TR” was running a zoological museum put together after seeing a dead seal at a market.  To deal with bullies, the scrawny boy took up boxing lessons, a hobby he would continue almost to the day he died.

A voracious reader with a photographic memory, Theodore Roosevelt eventually went on to Harvard where he graduated among the top of his class.

By 1884 it seemed TR had it all.  At age 23 he had already set his sights on becoming the youngest state representative in the history of New York.  Once in office, TR made news by exposing the corrupt relationship between a New York Supreme Court Justice and railroad magnate Jay Gould.  With his whirlwind enthusiasm and calculating mind, TR was easily reelected in 1882 and 1883, eventually being elected the youngest Speaker of the Assembly in the history of New York. 

Then tragedy struck.  After the joyful birth of his daughter Alice, on February 12th, his wife was diagnosed with Bright’s disease and died two days later on Valentine's Day.  Later that afternoon, TR's mother, Martha died of typhoid fever.  TR was inconsolable and wrote in his journal, “The light has gone out of my life.”

TR packed his things and headed west, to the Dakota Territory.  He wasn’t exactly welcome.  TR quickly picked up the moniker "four eyes" and "tenderfoot."  He proved his bravery in a saloon shortly after riding into town.  TR came in looking for coffee.  One of the thugs in the back of the bar took an instant dislike to him and made it known the bar was for whisky only.  At first TR simply ignored him but when the thug pulled two pistols he had to be dealt with.  So TR decked him.  Then, he pulled him outside and beat the man to a pulp. 

Later, TR was sworn in as a deputy sheriff.  One of the highlights of his career was when he led a posse of men after outlaw Mike Finnegan and his gang of thieves who stole a boat.  The chase lasted two weeks and covered 300 miles but TR eventually caught his man.  

Between travels around the country TR continued on as a deputy sheriff until permanently returning east in 1886.  From there his political career went straight up.  Nine years later TR was the police commissioner of New York City and he quickly set about cleaning house.  Within months a number of corrupt officers were fired, the world’s first police academy was established and a merit system of promotions was in place.

TR left the police department in 1897 to become Secretary of the United States Navy but even that was short lived.  In February 1898, the US was headed to war with Spain and TR was headed to the Army as a lieutenant colonel.  In July, TR was in Cuba where led the charge up San Juan Hill.  One hundred years later, President Bill Clinton awarded TR’s descendants the nation’s highest honor, the Congressional Medal of Honor.

Three years after the charge, TR had served as the governor of New York, vice president, and upon the September 14, 1901, assignation of William McKinley, President of the United States. 

His list of stunning accomplishments was not even close to done.  By the time TR left the presidency for good in 1909, he had established the National Park Service, laid the foundation for the construction of the Panama Canal, broken up huge corporate monopolies through anti trust regulation and won the Nobel Peace Prize.

TR continued his life as a private citizen making speeches around the US.  In October 1912, TR was shot in the head by someone in the audience.  The bullet smashed through his eye glasses and lodged in his skull.  TR refused medical treatment and told the crowd, “the bullet is in me now, so that I cannot make a very long speech but I will try my best.”

By the end of the First World War TR’s health was failing him.  He had lost his favorite son Quentin Roosevelt a year earlier when his plane was shot down by Germans over France.  Some say he never recovered from the broken heart. 

His last day was January 16, 1919.  TR told his manservant to “please turn out the light.”  He was found dead the next morning.  The official cause of death was listed as a pulmonary embolism brought on by the combined effects of inflammatory rheumatism and recurrent malaria.  When the news reached Washington, D.C., Vice President, Thomas Marshall, was reputed to have said, "Death had to take him sleeping, for if Roosevelt had been awake, there would have been a fight."

Authors note:  In keeping with a family tradition, TR would be proud to know his son; Brigadier General Theodore Roosevelt Jr. was awarded the Congressional Medal of Honor for his role in the invasion of Normandy June 6, 1944.  The awards make the Roosevelt’s part of a very elite class of Americans where a father and son duo have been awarded our nations highest honor. 

Grover Cleveland

Theodore Roosevelt