"It's hard to get behind strong odds that the deal is going to get approved," BTIG's Walter Piecyk told "Squawk Box" on Monday, referring to the talks between telecom companies Sprint and T-Mobile.
"The question is, do they require T-Mobile to give so much up, that you create a stronger fourth competitor than there would be if T-Mobile said, you know what, let's just let this deal go."
The New York Times reported on Friday that a merger approval for Sprint and T-Mobile may be near. The decision is dependent on the Justice Department's top antitrust regulator, Makan Delrahim, who recently approved the Walt Disney Company's acquisition of 21st Century Fox, but sued to block the deal between AT&T and Time Warner. He ultimately lost the latter case in court.
"No one really knows what Makan wants to do in terms of this transaction," said Piecyk. "We're dealing with a very uncertain regulatory environment, it makes it more difficult to make these strategic decisions."
For Piecyk, the chances of a deal going through are "less than 50-50."
Craig Moffett of MoffettNathanson sees a similar scenario playing out, as he also explained to "Squawk Box" on Monday.
"Even if you say, 70-30 Delrahim approves it, 70-30 the states lose and the deal gets through, even then you're only talking about a 49% combined chance that the deal gets approved. I think people are still too optimistic that this deal gets done."
Moffett also penned a note at the end of May calling the merger talks "Crazy Town."
In order for the deal to go through, Sprint and T-Mobile would have to sell the prepaid mobile service Boost, currently owned by Sprint. Bloomberg reported that the companies have approached Altice, Charter, and Dish Network about selling the service. This asset, along with Sprint-owned airwaves, are the subject of a suit by four attorneys general in New York and California.
For Moffett, the conditions are being placed on these companies strategically. "What the DOJ, what Delrahim actually wants in this is to create a set of conditions that makes T-Mobile decide they want to walk away, so he's never put int he uncomfortable position of saying yes or no."
"There's still a very real chance this deal gets blocked one way or the other."
Piecyk also doesn't see much upside to the merger. "T-mobile self-sustains, they have free cash flow, they can buy stock back...Sprint just needs to invest. And at this point, it might be too late, because the brand might be too damaged, and maybe that's something that Meakin has to consider."
"This has been a very odd process."