Cascade Bancorp in Bend, Ore., had until last Friday to secure $150 million of badly needed capital, and it remains unclear whether it got the funding.

Cascade has been mum on the status of a recapitalization deal that called for David F. Bolger and Donald Marron's Lightyear Capital LLC to invest $65 million in the $1.9 billion-asset company. Cascade, which has been under a regulatory order to raise capital since August 2009, must raise an additional $85 million on its own. After pushing back a deadline, initially May 31, several times, Bolger and Lightyear gave Cascade until Nov. 5 to satisfy the deal's closing conditions.

Bolger declined to comment on the deal's status Wednesday. Cascade and Lightyear did not respond to queries.

"I think it's kind of a mystery," said Timothy Coffey, an analyst at FIG Partners LLC. "I think that the longer it takes to complete it, … the harder it is to convince investors that this is a good deal."

The parties' silence is not necessarily a sign that the deal is off.

"They've rolled forward the commitment multiple times, and there's no reason to believe that the expiration last Friday is any reason to panic [or] that those anchor investors are gone," said Jeff Rulis, an analyst at D.A. Davidson & Co. Cascade needs about $115 million to fill its capital hole, he said.

At Sept. 30, its leverage ratio was 3.9%. "This effectively is a do-or-die situation," Coffey said.

Cascade has given little insight into what has held up the deal, which was announced in November 2009. It sued Cohen & Co. Financial Management in August, alleging the latter was holding up the deal by failing to honor an agreement to transfer $66.5 million of trust-preferred securities to Cascade for $13.3 million in redeemable notes, which would be paid at the effort's closing.

At the time, Cascade Chief Executive Patricia Moss said investors were unwilling to pony up until Cascade could trim some of its debt. In an Aug. 23 court filing, the Oregon banking company said it was close to a resolution with Cohen. On Sept. 2, it voluntarily dismissed the lawsuit.

Subscribe Now

Access to authoritative analysis and perspective and our data-driven report series.

14-Day Free Trial

No credit card required. Complete access to articles, breaking news and industry data.