In a sign that Pacific Capital Bancorp’s bondholders may play hardball as it tries to pull together a crucial $500 million rescue deal, the banking company said June 30 that it has again extended the deadline for its debt securities to be cashed in.

Bondholders of just $68 million of outstanding debt have turned in their securities, the bank said. That number represents about 52 percent of the total outstanding debt that the firm needs for its recapitalization deal go through.

Debt holders have a new tender deadline of July 26, but still face terms that will cash them out at 40 cents to 65 cents on the dollar.

Bondholder cooperation is crucial for Pacific Capital, the struggling parent firm of Santa Barbara Bank & Trust, to get a $500 million rescue deal done. Under the terms of the recapitalization plan, 70 percent of the bank’s outstanding debt — or $131.8 million — must be cashed in.

The banking company has repeatedly failed to meet capitalization requirements laid out for it by federal regulators. Now the firm is facing a Sept. 8 deadline to boost capital levels or potentially be sold or liquidated.

For a $500 million infusion from Texas-based Ford Financial Group to go through, Pacific Capital’s stakeholders need to make some heavy concessions.

In addition to getting the approval of bondholders, the deal also needs the go-ahead from the U.S. Treasury, which must agree to take stock in exchange for one-fifth of its $180 million in bailout money and write off the rest. The expiration of TARP funding this fall means the Treasury may be highly motivated to swap its debt for equity.

Bondholders have pushed back from the beginning, with only $50 million in outstanding debt tendered by June 15. The bank decided to sweeten its offer then, doubling the cash price it would pay to bondholders and extending the deadline to June 30.

Brian Kuelbs, a consultant to banks around the country who is familiar with how such negotiations work, told the Business Times on June 25 the Ford deal is “more likely to get done than not.”

“But these things are extremely volatile,” he added. “I don’s suspect that it’s much more than 60 percent likely to get done. A lot of things can happen. I’m sure they’re negotiating constantly on the economics and the terms.”

Pacific Capital’s leaders have displayed confidence in their ability to persuade the various sides to cooperate, with CEO George Leis telling the Business Times in May that he felt the deal had “a strong chance of closing.”