ESPN is closing in on a new deal with its biggest pending free agent: Dan Le Batard.

The outspoken TV/radio host of ESPN's "Highly Questionable" and ESPN Radio's "The Dan Le Batard Show with Stugotz" is finalizing a long-term contract extension, according to Sporting News sources. The 49-year-old Le Batard's current deal is slated to expire early this summer. However, the sources said the new deal is not signed yet.

Keeping Le Batard would be a feather in the cap for the new ESPN management team of president Jimmy Pitaro, Oscar-winning content czar Connor Schell and executive vice president of studio production Norby Williamson. Le Batard has discussed moving his ESPN radio show to Sirius XM Radio, according to Ryan Glasspiegel of The Big Lead. The lure? Le Batard would be able to build out his own station at Sirius XM.

In recent years, ESPN has lost stars such as Colin Cowherd, Skip Bayless and Erin Andrews to Fox. Despite three rounds of layoffs, ESPN has fought back in the talent wars, luring Adrian Wojnarowski from Yahoo and Katie Nolan from Fox, while hiring back Rachel Nichols from CNN and Michelle Beadle from NBC. ESPN declined to comment; Le Batard's agent, Trace Armstrong, did not return calls.

As Game 2 of the #NBAFinals approaches, we look back at Friday's show as the guys and their panel of "experts" tried to figure out what happened in those final seconds of regulation of Game 1 in a little segment we call - "What The Hell, Man!?"

- Lorenzo pic.twitter.com/pWFzQ4vtjr — Dan Le Batard Show (@LeBatardShow) June 3, 2018

Le Batard is close friends with former ESPN president John Skipper, leading some to speculate he'd bolt after Skipper's sudden departure in December.

A red-eyed Le Batard choked back tears on the air when he learned about Skipper's abrupt resignation due to a substance addiction. "This person has created everything that exists here at ESPN for us," Le Batard said. "He did it because of how he cares about minorities and their causes."

The son of Cuban exiles from Fidel Castro's Communist Cuba, the Miami-based Le Batard is one of ESPN's funniest, most entertaining talents.

The longtime Miami Herald columnist co-hosts "The Dan Le Batard Show with Stugotz" radio program with Jon "Stugotz" Weiner weekdays from 10 a.m to 1 p.m. ET (simulcast on ESPNEWS). His show addresses pop culture as much as sports. He and his producers don't take sports, or themselves, too seriously.

Then he and dad Gonzalo "Papi" Le Batard co-host "Highly Questionable" on weekday afternoons from 4:30-5 p.m. The light-hearted afternoon TV show shot at the Clevelander Hotel in Miami Beach sets the table for the 1-2 punch of "Around the Horn" and "Pardon the Interruption" between 5-6 p.m.

The world is burning, Trump is trying to start fires on our playground. And I'm sitting here terrified of what mascot head Corso will put on — Dan Le Batard Show (@LeBatardShow) September 23, 2017

Le Batard and producer Erik Rydholm have generously invited a rotating series of young ESPN talent to learn the trade on "Highly Questionable," ranging from Bomani Jones and Sarah Spain to Mina Kimes and Pablo Torre. Jones parlayed his four-year run on "Highly Questionable" into the new "High Noon" TV show with Torre (noon). Le Batard himself first shot to national fame by guest-hosting "Pardon the Interruption" with Tony Kornheiser and Michael Wilbon.

Like Kornheiser, Jemele Hill and Stephen A. Smith, Le Batard pushes the envelope with his edgy opinions and irreverent humor. ESPN suspended Le Batard for his billboard stunt "thanking" LeBron James after the NBA superstar left the Miami Heat for his home-state Cavaliers in 2014.

ESPN management hates it when on-air talents criticize colleagues (internally calling it "ESPN on ESPN crime"). But Le Batard has survived ripping colleagues ranging from Sage Steele and Bayless to Cowherd and Jay Bilas over the years, noted Awful Announcing. From his exile at The Ringer in Los Angeles, former ESPN bad boy Bill Simmons can only watch in envy.

I don't know where Trump draws the line as he picks unpresidential fights with basketball and football. I think the line might be hockey. — Dan Le Batard Show (@LeBatardShow) September 23, 2017

And Le Batard can stir it up. Like the time he gave his baseball Hall of Fame ballot to Deadspin. Or recently questioning NBA legend Magic Johnson's qualifications to run the Lakers.

Le Batard attributed the hire to Magic's fame and charm. That drew an angry response from ESPN colleagues like Michael Wilbon of PTI and Keyshawn Johnson. Le Batard blamed the reaction on the larger race problem in the U.S., according to the New York Post. “The social justice warriors are eating their own," countered Le Batard. "I found it interesting what it became. It’s instructive to what happens in America now.”

Le Batard has bristled over President Donald Trump's feud with colleague Jemele Hill and kneeling NFL players, as well as the charge that a left-wing "MSESPN" has turned off conservative viewers and listeners.

Besides Hill, if there's one talent at ESPN who's likely to challenge the company's internal guidelines against "overt" political partisanship or anything that would "embroil the company in an unwanted controversy," it's probably Le Batard. But will that continue with a new deal? We'll see.