[3] Eskin got his start in local radio at WFIL in 1972 when evening shift disc jockey George Michael hired him to be his engineer.

[1] Eskin's years on the air allowed 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, Jayson Werth and Cole Hamels.

On television Eskin helped launch WTXF-TV's Ten O’Clock News as the station's original sports director from 1986 to 1991.

He also previously served as a contributor to The George Michael Sports Machine, ESPN's First Take, The Dan Patrick Show and The NFL Network.

[6] In 2012, Eskin returned to WTXF as a contributor to the station's coverage of Eagles football (of which it carries most of the team's games through its network package.

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.

His involvement in the negotiation entailed a request for help from Allen L. Rothenberg, a prominent Philadelphia attorney, who was a regular at Eskin's synagogue.

Eskin has also been known to lead long-term "campaigns" to have players traded from Philadelphia teams such as former Philadelphia Phillies' outfielder Bobby Abreu for alleged lackadaisical defense and lack of clutch hitting, and Sixers' guard Allen Iverson for his allegedly selfish play, though he has subsequently praised Iverson.

Eskin's last public stunt was organizing a mock funeral to celebrate Terrell Owens's demise with the Philadelphia Eagles during their 2005 season.

He also refers to the Pittsburgh Steelers as the "Stillers" and stereotypes their fans as IronCity beer drinkers, smokers, and generally of a low-class demeanor.

On his current Saturday show during the NFL season, he reviews and picks games with Marc Lawrence, a sports handicapper.

[9] In 2000, Eskin was suspended and forced to give an on-air apology to the organizers of the Miss America pageant for saying on the air that the contest was rigged.

[10] During the beginning of the 2007 Phillies season, Eskin criticized the team for not taking chances with their payroll and instead running their sports franchise like a "department store".

Eskin often touts his affinity for a wardrobe that includes expensive jewelry and clothing, particularly fur coats for Eagles home games.

[1] Eskin has also raised more than $100,000 in funds for the Brandywine Valley SPCA and Providence Animal Centers and organized fundraising drives for the victims of Hurricane Katrina.