Town of Pawling, village of Pawling, hamlet of Holmes
Town of Carmel, halmets of Mahopac, Mahopac Falls
Town of Patterson, hamlets of Putnam Lake, Towners
Town of Southeast, village of Brewster, hamlets of Dykemans, Peach Lake, Tilly Foster
Town of North Salem, hamlets of Croton Falls, Purdys
Town of Somers, hamlets of Amawalk, Baldwin Place, Granite Springs, Heritage Hills, Lincolndale, , Shenorock
Town of Yorktown, hamlets of Crompond, Croton Heights, Huntersville, Jefferson Valley, Kitchawan, Mohegan Lake, Shrub Oak, Yorktown Heights
Parts of Dutchess, and Putnam
All of Putnam
While no challenger has officially filed to take on the district's freshman incumbent legislator, several names have emerged in the media as potential challengers contemplating a bid.
On March 17, 2008, Ball announced that he would be a candidate for reelection during an event at an Irish restaurant in Yorktown Heights, flanked by new Westchester GOP Chairman Douglas Colety, Putnam GOP Chairman Anthony Scannapieco, Jr., and Westchester County Executive candidate Rob Astorino. Ball highlighted the fact that his campaign had received the most money and more contributions from individual donors then any other incumbent minority Assemblyman in the last quarter of 2007. In a speech to supporters, Ball stated that "I'm a maverick Republican. I came into this business from outside the political machine. That makes me a target for Albany insiders."
John Degnan, former Mayor of the village of Brewster, New York, stated he was in the race in May of 2008. He has been endorsed by the Southeast Republican Committee (unanimously), and won the Putnam County Republican Committee's backing by a vote of 97-50. The Westchester Republican Committee narrowly endorsed Ball over Degnan, while the Pawling Republican Committee--the only Dutchess GOP committee in the 99th Assembly District--chose not to endorse either candidate. Though a lifelong Republican, Degnan was also subsequently backed by the Putnam County Democratic Party Committees, and leading Democrats in Westchester County.".
Although no challenger has officially filed to run against the freshman incumbent Greg Ball, there had been speculation in the media that County Legislator Mike Kaplowitz, who failed in a 2006 bid for State Senate, will be challenging Ball. In April of 2008, Kaplowitz ruled out challenging Ball. 2006 challenger Ken Harper is also said to be mulling a second run at the office.
The 2006 New York State Assembly election for New York's 99th District matched conservative Republican Greg Ball and Democrat Ken Harper against the Conservative and Independence Party incumbent Will Stephens. The Democratic Party of New York had targeted the seat as a potential pickup after the incumbent was defeated by a wide margin in the primary by a strong, well-funded challenger.
On September 12, 2006, in the Republican Primary for New York's 99th District, Ball defeated Stephens in a landslide with 70.4% (5,165 votes) to 29.6% (2,176 votes) for Stephens, the lowest vote total for any incumbent running for reelection to the State Assembly that day.
Despite Willis Stephens name remaining on the ballot, Ball went on to win a plurality of votes in the general election on November 6, 2006. His upset victory earned him the title of "Newsmaker of the Year" from one local publication and he also shared a front-page cover The Journal News with fellow upset winer John Hall the day after election day.
The primary campaign was a bitter one, with Ball railing against the 'machine politics' of Willis Stephens and Putnam County. The Ball campaign out raised Stephens by a significant margin, giving him a visible presence in local newspapers and television outlets. According to the last filings prior to the primary, Stephens had $13,198.38 on-hand, while Ball had $86,117.03 of the money he has raised remaining. Stephens drew criticism for not returning campaign contributions from the Victory Fund-a political action committee that took contributions from indicted trash magnate James Galante.
On September 12, 2006, in the Republican Primary for New York's 99th Assembly District, challenger Greg Ball, defeated the incumbent Willis Stephens, by a mammoth margin: 71% for Ball, 29% for Stephens. Stephens claimed he had been the victim of a negative campaign, citing mailings that were distributed calling him a 'country-club liberal' and hilighting his close relationship with Assembly Speaker Sheldon Silver. However, Stephens himself drew criticism when he refused to repudiate a letter about challenger Greg Ball which falsely claimed Mr. Ball had received a dishonorable discharge from the United States Air Force. Ball did not dispute that he ran hard for his seat, knocking on 10,000 doors prior to the primary.
Greg Ball, a retired Air Force Captain and Vice President of Exceed International Development Corporation, scored a major upset when he defeated the incumbent Stephens in the September 12th primary by nearly a three to one margin.
The Ball campaign picked up steam since Stephen's wayward email referring to his constituents as 'idiots', and another letter purported to be sent by the Stephens campaign which claimed that Captain Ball received a dishonorable discharge, which was discredited when a copy of Captain Ball’s DD-214 showed he had received an honorable discharge. Stephens insisted neither he, his staff nor anyone associated with his campaign had knowledge of the letter and his involvement was never proven.
Ken Harper, the Chairman of the Putnam County Democratic Committee, ran unopposed for the Democratic nomination. He is known for writing frequent letters to the editor in local newspapers. Harper had failed in six previous bids for public office including Putnam County Executive in 1998 and 2002, Putnam County Legislator in 2003, Patterson Town Supervisor in 1997 and 1999, and Paterson Town Councilman in 2005. Although in other years, the previous incumbent had been challenged by only token opposition, this would be the first that the seat would be competitive in over a decade. Harper received funding of over $250,000 to Ball’s from the New York State Democratic Assembly Campaign Committee (DACC) for the campaign. However, he was unable to prevail.
Harper criticized his opponent after he pointed out to The Journal News that a League of Women Voters brochure inaccurately listed Harper was a college graduate. Ball said a note that appeared after Harper's name, stating that the Democrat graduated from the University of Pennsylvania in 1982 with a bachelor's in English, was false. Both a university spokesman and Harper confirmed that fact, stating that Harper attended the institution, but that there was no record of him having received a degree. Harper stated he never misrepresented himself as a college graduate and was not responsible for the content of the panthlet.
Six-term incumbent Will Stephens II, 48, ran for re-election in the Republican Primary in September 2006 for the seat once held by his father and grandfather. After losing the Republican Primary, due to New York's electoral fusion system, the Assemblyman had vowed to remain in the race on the Conservative and Independence lines. Ultimately, Stephens decided to withdraw from the race altogether, instead taking a nomination for Supreme Court Justice in Queens, in order to allow Ball ballot access on the Independence and Conservative lines. Although Stephens attempted to have his named removed from the ballot, Harper, the Democratic nominee, sued the State Board of Elections claiming that Stephens had filed a certificate declining his nomination eight days too late. The New York Court of Appeals eventually ruled that Stephens name should remain on the ballot.