(Bloomberg) -- Byron Allen’s offer to buy Paramount Global is the media executive’s biggest takeover bid yet, leading a $40 billion-plus list of potential targets that’s spanned entertainment networks to National Football League teams. 

If successful, it’d be a rare triumph among his headline-grabbing attempts at big mergers and acquisitions, many of which have been thwarted by deep-pocketed counter bidders or regulatory hurdles. 

Allen on Tuesday confirmed he’d made a $14.3 billion proposal to buy the outstanding shares of Paramount. Including debt, the deal could be valued at about $30 billion. In a letter he sent to Paramount that was reviewed by Bloomberg News, Allen said he would finance the offer with a combination of secured and unsecured senior debt and equity.

Allen, a former stand-up comic turned media mogul, has a net worth of about $735 million, according to Bloomberg estimates. While Allen’s ownership of his company accounts for the bulk of his net worth, he also has tens of millions of dollars in personal properties, cash and liquid investments, the estimates show.

A representative for Allen didn’t immediately provide comment.

BET, Disney Networks

The Paramount offer comes after Allen last year reiterated his $3.5 billion bid for Paramount’s Black Entertainment Television and VH1 channels, and separately offered $10 billion for Walt Disney Co.’s flagship ABC TV network and FX and National Geographic cable channels. 

Disney’s Chief Executive Officer Bob Iger said late last year that he isn’t considering a sale of those assets, denting Allen’s aspirations. Meanwhile, Paramount was most recently in talks to sell BET to a management-led investor group, though no deal has yet been announced. 

In 2020, Allen made an all-cash offer for Tegna Inc. that valued the TV station owner at $8.5 billion including debt. That bid was backed by debt and equity financing from Oaktree Capital Group, Fortress Investment Group, the family office of Michael Milken and Ares Management Corp., people familiar with the details said at the time. 

Tegna eventually agreed to a deal with hedge fund Standard General, only to see that fall apart after a deadline to get approval from the Federal Communications Commission passed. Allen has said he remains interested in Tegna and that regulation rather than financing is the main obstacle to any deal.  

Then there have been the sports bets. 

In 2022, Allen threw his hat in the ring as a bidder for the Denver Broncos, a move that would have made him the first Black majority owner of an NFL team. Walmart Inc. heir Rob Walton eventually agreed to buy the Broncos for more than $4.5 billion, after which Allen mulled a bid for the Washington Commanders. That team was sold the following year to a group led by private equity billionaire Josh Harris for $6 billion.

Read more: Paramount’s Fizzling Rally Shows Market Doubts on Allen’s Bid

Local Stations

Allen’s dealmaking chops have helped him build Allen Media Group, which he founded in the early 1990s, into one of the largest privately owned media companies in the US, with networks such as Pets.tv, Cars.tv and Recipe.tv. 

He’s spent more than $1 billion in recent years adding assets including the Weather Channel and a string of local TV stations from Honolulu to Tucson, Arizona. In 2019, he was a minority investor in Sinclair Broadcast Group Inc.’s $9.6 billion acquisition of the Fox regional sports networks from Walt Disney. 

More recently, Allen has been weighing a bid to purchase several TV stations from broadcaster E.W. Scripps Co. and seeking funding from the private debt market to pay for the potential deal, Bloomberg News reported. 

An Allen Media Group loan maturing in 2027 is currently trading at around 90 cents on the dollar, data compiled by Bloomberg show. 

In the past, Allen has spoken of having a better chance of acquiring media assets than private equity firms or big technology companies because he’s already won regulatory approvals to own stations. A takeover of Paramount, which also owns a film studio, real estate and various intellectual property rights, would be his biggest to date and could test this theory. 

For now, it pits Allen against David Ellison, the US media executive who owns film and TV studio Skydance Media. Ellison has made a preliminary offer to buy National Amusements Inc., the holding company of the Redstone family, as a way to take control of Paramount. He’s also had discussions with Paramount about merging Skydance into the larger media company after he takes control. 

Paramount’s non-voting shares rose as high as $15.70 on Wednesday following Allen Media Group’s offer. The stock then sank below $15, leaving them well below Byron’s bid, signaling the market is far from certain things will pan out.

--With assistance from Michelle F. Davis, Christopher Palmeri, Vernal Galpotthawela, Devon Pendleton, Lara Wieczezynski and Neil Callanan.

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