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After Eskin graduated from Northeast High School in Philadelphia in 1968, he got his start in local radio at WFIL-AM when evening shift disc jockey George Michael hired him to be his engineer. Eskin eventually made a name for himself in sports radio by breaking stories and stirring public opinion with his commentaries. He brought that same hustle with him to television where, with his efforts, breaking news was often found on the sports desk. The award winning sportscaster first made the transition to television in 1982 when he joined KYW-TV. One of Eskin’s managers at KYW jokes that the sportscaster kept the Eagles in Philadelphia by breaking the story in the 1980s that the owner was trying to sell the team. "If Howard had not stepped in when he did... Leonard Tose would have snuck the Eagles out of town," says Frank Traynor. "Howard broke the Eagles story... and, by doing so, I believe helped to keep the team in town."
In the mid-1980s, Eskin co-hosted with John Debella on WMMR's Morning Zoo, their combination was advertised as "Sports Rock". On television Eskin helped launch Fox Station WTXF-TV's Ten O’Clock News as part of its original anchor team from 1986 to 1991. On radio, the "Sports Rock" format proved unsuccessful at WMMR. It began in the Fall of 1992 and lasted until the Spring of 1993. Soon thereafter, Eskin moved to WIP, whose station format would shortly become amongst the first full-time sports-talk radio themes in the United States.
In 1992, he rejoined KYW-TV and then moved to WCAU-TV in 1996 where he served as a host and contributor to Sports Final until April, 2005. He returned to the show in 2006. He was also a contributor to the The George Michael Sports Machine, hosted by the man who helped Eskin begin his broadcasting career; serves as a frequent commentator on ESPN's First Take; co-hosted a nationally syndicated radio show, Let’s Talk Sports, and been called on for his opinions by such diverse programs as NBC’s Today Show and PBS’s MacNeil/Lehrer News Hour.
In addition to his radio and television presence Eskin wrote a column for the Philadelphia Daily News in the early 1990s.
Eskin's breaking stories included one that former Philadelphia Phillies general manager Ed Wade would be fired if the Phillies did not make the playoffs. Wade was subsequently fired by the Phillies on October 10, 2005. He unsuccessfully "campaigned" for the GM position, that was eventually filled by former Toronto Blue Jays GM Pat Gillick.
Eskin also covered the negotiation and subsequent breakdown between Comcast and a group led by Julius Erving and Will Smith to buy the Philadelphia 76ers. Howard's involvement in the negotiation entailed a request help from Allen L. Rothenberg, a prominent Philadelphia attorney, who was a regular at Eskin's synagogue.
On September 20, 2007 Howard Eskin logged his 5,000th radio show, more than anyone else in the country, and celebrated his 25th year in television that same year. Guests on the show included Charles Barkley, Terrell Owens, and Billy Cunningham.
On September 2, 2011 Howard Eskin hosted his last 3 to 7 PM show after nearly 6,000 shows and 25 years in that slot.
In 1997 Eskin was exposed as the "prominent Philadelphia sportscaster" who had sent a dozen roses to a woman five days before she was murdered by her husband. The woman had posted a fake profile on a dating site, identifying herself as 25-year-old "Brandice". A note sent with the roses was read during the guilty plea of Raymond Stumpf by his attorney: "Dear Brandice It was absolutely wonderful getting to know you. Hope to get to know you better. You were very thought-provoking and I do love your name. Love, Howard." Eskin subsequently denied ever meeting with her and said the roses were nothing more than an innocent attempt to brighten a lonely woman's day. At his sentencing, in Montgomery County Court, Raymond Stumpf stated "I think the worst part was probably the day the roses came." Stumpf was sentenced to a term of 7 1/2 to 15 years for the killing.
Howard is best known for his controversial comments in regard to teams, coaches, athletes, sportswriters, broadcasters, and listeners and sometimes non-sports related issues. It is not uncommon to hear Eskin defend one of his "favorites" against a popular critical opinion, or disregard a milestone accomplished by someone who he doesn't "like." One example of this is when he recently slammed Roy Halladay, in the off-season after Halladay pitched the MLB's 20th perfect game ever and the second ever no hitter in the playoffs, for not speaking to the media enough and not disclosing his opinions on matters where his opinions had already been made public and quotes from Halladay had already been released to the media.
During a controversy involving former Philadelphia Flyer Eric Lindros selling game tickets to Mafia members, Eskin interviewed reputed Philly mob boss Joseph Merlino about the Mafioso's sitting in Lindros' seats at a hockey game at the Flyers' rink. Merlino denied getting the seats from Lindros.
Eskin has also been known to lead long-term "campaigns" to have players traded from Philadelphia teams such as former Phillies' outfielder Bobby Abreu for alleged lackadaisical defense and lack of clutch hitting, and Sixers' guard Allen Iverson for his allegedly selfish play. Eskin's last public stunt was organizing a mock funeral to celebrate Terrell Owens demise with the Eagles during their 2005 season.
In 2007, Eskin criticized the Philadelphia Phillies for not taking chances with their payroll and running their sports franchise like a "department store." After a 3-9 start to the team's 2007 season, Eskin had a publicized confrontation with manager Charlie Manuel, implying that he was not tough enough on his players and goading him into yelling and threatening Eskin in the press room, Manuel's office, and in the Phillies' clubhouse.
Eskin often touts his affinity for a wardrobe that includes expensive jewelry and clothing, particularly fur coats for Philadelphia Eagles home games. In his "honor", Philadelphia Daily News writers dubbed Eskin "The King of Bling,". Eskin sold a bobblehead doll of him wearing a fur coat, with the proceeds going to charity, in 2004 and 2005, which raised 75,000 dollars for charity. The first 100 dolls in the 2005 version came with a special small diamond chip in his "bling" necklace.
He has sponsored numerous charity and fund-raising events off-the-air to benefit a particular humanitarian cause throughout the years, most recently for victims of Hurricane Katrina. On the air, he has advocated for issues such as public smoking bans and medical tort reform.
Though Eskin regularly initiates calls with comments such as "never had a bad day in my life" or "another day in paradise", he is known to be short-tempered and easily angered on his radio show if a particular caller does not agree with his viewpoints. He frequently refers to a caller as a "genius" or "chief" (both sarcastically), a "dope", an "idiot", a "nitwit", a "creep" or a "moron".
He is known to ask female callers about preparing dinner or washing the laundry and he calls obviously black callers "dawg" while sarcastically closing those conversations with the urban vernacular "holla". In addition, Italian callers are often addressed as "cuzz" and Dallas Cowboys' fans are termed "cock-a-roaches". Howard at times will tell callers if they are worried about their team, "If you're scared, get a dog." Derisively, he baits Pittsburgh Steelers fans by pronouncing them as "Stiller" fans and stereotypes them as IronCity beer drinkers, smokers, and generally of a low-class demeanor while disdainfully criticizing their winning accomplishments.
Eskin's years of infamy in the Philadelphia sports scene allow him to frequently have special guest athletes or other sports figures on his program, with memorable interactions with Charles Barkley, Freddie Mitchell, Terrell Owens, Lenny Dykstra, Andre Iguodala, Bernard Hopkins and Cole Hamels.
Eskin also has more of an affinity towards sports gambling than other co-hosts. On Friday afternoons during football season, he often has a "handicapping expert" on as a guest. In addition, he is the self-proclaimed "King of Monday Night" due to his successful track record in picking Monday Night Football games correctly. When his time slot was Monday evenings, he would often tease and mock his callers waiting for him to announce his Monday Night pick, calling them "degenerates".
Eskin's nickname, "King", was given to him by Pete Rose.
The Broadcast Pioneers of Philadelphia  inducted Eskin into their Hall of Fame in 2011.