ESPN radio

In 2001, Astorino was one of the founders of 1050 ESPN Radio in New York.^[7][8][9] He directed the rebranding of New York's WEVD-AM 1050 from a talk radio station to an all sports format.^[10] He became the station's Senior Producer, and worked as Executive Producer of The Michael Kay Show.^[11] He was promoted to Station Executive Producer and served until 2005, when he resigned to run for Westchester County Executive.^[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.^[14][15] His accomplishments include securing broadcast rights for the New York Knicks and New York Rangers, also at the expense of WFAN.^[14]

Satellite radio

In 2007, Astorino was hired as the first program director for Sirius Satellite Radio's "The Catholic Channel".^[7] He hosted a Thursday night program with Cardinal Edward Egan, the Archbishop of New York.^[7]

Astorino was hesitant at first to work on religious radio, but he changed his mind when he found out "The Catholic Channel" would be different.^[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. Egan, who is not known to be a great communicator like his predecessor, Cardinal John O'Connor, gave the project his blessing. In addition to his show, he welcomed Sirius listeners when Sunday Mass from St. Patrick's Cathedral was broadcast."^[16]

Westchester County Legislature

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.^[20] He helped the board stop Westchester's payments of a "franchise fee" to their bus operator, Liberty Lines Transit, after drawing attention that the contract with the company did not provide for such a payment.^[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.^[22] As an outgoing legislator, he opposed the pay increases that were enacted for board members.^[23]

Campaigns

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.^[26][27] Overall voter turnout was light and incumbents were largely successful throughout Westchester County.^[28]

On March 21, 2009, Astorino announced that he would run again for Westchester County Executive.^[27][29] In a surprising upset, he was elected to the position on November 3, 2009, defeating incumbent Andy Spano by 15 percentage points.^[30]

Astorino ran for re-election in 2013. He defeated his challenger, Democratic candidate Noam Bramson,^[31] by 12 percentage points.

Astorino sought a third term in 2017, despite his statement during the 2014 campaign that "eight years is enough for anyone" in office.^[32] During the campaign, Astorino outspent his opponent, State Senator George Latimer, by more than 3-to-1.^[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.^[34][35][36] Towards the end of the campaign, on October 27, 2017, Astorino was damaged by revelations from testimony in the Norman Seabrook trial. Campaign donor Jona Rechnitz testified that he had paid $5,790 to cover most of the cost of a Rolex Submariner for Astorino shortly before Astorino named him as a chaplain for the Westchester County Police.^[37][38] Another controversy in the closing days of the race was the disclosure of an email from an Astorino lieutenant to county employees that they should "expect to donate their time" by using paid time off to volunteer for Astorino's campaign.^[39][40] Despite his fundraising advantage, Astorino was defeated by 14 points.^[41]

Campaign donors

As of September 2016, Astorino had received $15,000 in campaign contributions from Donald Trump; he has stated that he considers Trump a friend.^[42]

As of November 2017, Astorino had been the biggest beneficiary of donations by Robert Mercer to state and local campaigns in New York.^[43] Mercer and his daughter Rebekah each gave the maximum $26,900 to Astorino's 2013 reelection campaign.^[44] Additionally, Mercer gave $1.55 million to a super PAC supporting Astorino's 2014 gubernatorial campaign and $1 million to a super PAC supporting Astorino's 2017 re-election campaign.^[45]

Tenure

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In 2010, the Westchester County Legislature passed a $1.2 million bond issue to finance the restoration of the Elijah Miller House. Astorino, who had previously supported preserving the building five years earlier as a member of the legislature, vetoed the measure, saying it should be supported by private funds.^[46]

Lawsuit from the Westchester Independence Party

On October 31, 2013, the Westchester Independence Party filed a suit against Astorino and other defendants, alleging that Astorino and his campaign attempted to win the party's nomination by coercing dozens of staff members, political associates, friends, and family members to switch their party affiliation to the Independence Party. The lawsuit alleged Hatch Act violations and also included allegations of racketeering, conspiracy, and wire and mail fraud. On September 29, 2015, U.S. District Judge Kenneth Karas dismissed the case.^[58] Astorino used Westchester County funds to pay $279,391 in legal fees for his defense rather than having his campaign pay for them. The move was described as a "borderline call, at best" by the New York Public Interest Research Group.^[59]

Norman Seabrook trial

In 2016, Astorino's office received subpoenas from U.S. Attorney Preet Bharara in conjunction with an investigation into Jonah Rechnitz. Various companies tied to the Brooklyn-based businessman donated a combined $25,000 to Astorino's 2014 gubernatorial campaign.^[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. Rechnitz later testified in the federal corruption trial of disgraced NYC corrections union boss Norman Seabrook to a history of quid pro quo with Astorino in which he helped Astorino obtain a $10,000 Rolex Submariner watch that was later confiscated by federal investigators.^[61][62] Astorino denied any wrongdoing and claimed that he went jewelry shopping with Rechnitz because they were meeting next door.^[63][64] Astorino claimed that he paid for the watch in full, but the FBI entered into evidence a $5,790 check with the memo line "ROLEX" cut by Rechnitz to Daniela Diamonds, which sold Astorino the watch. Rechnitz testified that Astorino knew about the check.^[65] An investigation by Andrew Whitman of FiOS1 showed that the $1,960 Astorino paid for the watch was unrealistically low, but that the cumulative total of $7,750 paid by Astorino and Rechnitz combined would be a typical price for a watch of that age and model.^[66] As of June 2019, Astorino had not been charged with a crime in connection with the purchase of the Rolex.^[67]