In 2017, Astorino ran for a third term as Westchester County Executive, but was defeated by Democratic challenger George Latimer.

He and three detectives were seen on film taking $10,000 during an FBI sting; Robert Astorino pleaded guilty and was sentenced to one year in prison.

[12][13] As the producer of the 4:00 to 7:00 PM time slot, the team of talent assembled by Astorino included Michael Kay, Don La Greca, and Joey Salvia; this team helped the show succeed against longtime afternoon sports radio mainstay Mike and the Mad Dog on WFAN.

[16] He stated, "I think it's a great opportunity not just for the archdiocese but for the Catholic Church as a whole to reach out to people across the country with a message, and have a two-way conversation.

"[7] According to the Journal News, "With total authority over programming, the Archdiocese of New York was given the rare opportunity to play Michelangelo and create something new.

[2] In 2003, Astorino announced he was a candidate to replace retiring County Legislator Sue Swanson, who represented a district encompassing Mount Pleasant, Pleasantville, North Castle, West Harrison, and portions of northern Greenburgh.

[18] Astorino defeated his challenger with an aggressive campaign, which according to the Journal News, "raised the bar" for candidacies to the Board of Legislators.

[19] As a county legislator, Astorino was involved in plans to redevelop the Saw Mill River Parkway and restore wetlands, which is often flooded dangerously during rain storms, and coordinated meetings between the environmentalist groups, New York State Department of Transportation and the United States Army Corps of Engineers in 2005.

[21] Once elected, he served on the committees for parks and recreation; housing; health; public safety and criminal justice; youth; and county officers and departments.

[2] After serving only two years, Astorino opted not to run for reelection, instead focusing on a challenge to incumbent County Executive Andy Spano.

[23] The 2005 campaign for Westchester County Executive pitted the two-term Democratic incumbent Andy Spano, against Astorino, a Republican.

[6] The race featured instances where Astorino publicized a homemade video of a security breach at the county's Kenisco Dam, while the incumbent, according to the New York Times, "in the face of record property-tax increases, has busied himself with a campaign against steroids for schoolchildren, as a follow-up to an anti-bullying initiative that featured admonitions from Spider-Man.

"[24][25] Facing an uphill battle in a Democratic county against an incumbent who raised four times as much money as he did, Astorino made a surprisingly strong showing and was defeated by 30,000 votes.

[27][29] In a surprising upset, he was elected to the position on November 3, 2009, defeating incumbent Andy Spano by 15 percentage points.

[33] Additionally, Astorino was the beneficiary of over $1 million spent in the last two weeks of the race by a super PAC funded by Robert Mercer.

[45] In 2010, the Westchester County Legislature passed a $1.2 million bond issue to finance the restoration of the Elijah Miller House.

[46] On March 5, 2014, Astorino announced that he would run for New York State Governor against incumbent Democrat Andrew Cuomo.

[48] After the election, news broke of a pact between then Democratic Governor Andrew Cuomo and Republican State Senate Majority Leader Dean Skelos.

[50] In June 2020, Astorino announced his campaign for New York's 40th State Senate district against incumbent first-term Democrat Peter Harckham.

[60] Astorino in turn made Rechnitz and friend Jeremy Reichberg county police chaplains and provided both with special parking permits despite the fact that neither man was a member of the clergy.