Perhaps Irving Place Capital's knottiest acquisition ever, buying Chesapeake Corp. out of bankruptcy for $485 million in June, was largely the handiwork of the youngest of the New York buyout firm's 12 senior managing directors. Phil Carpenter III, 37, says his boss, Irving Place CEO John Howard, "really navigated Chesapeake through an arduous bankruptcy."

Blond-haired, cerulean-eyed and sturdily built, Carpenter looks more like a well-groomed surfer than a typical Wall Street "suit." Self-effacing with respect to his accomplishments, he's openly proud of the work ethic that his father, a retired teacher, and his mother, a nurse, instilled in him as a boy growing up in Bayshore, Long Island. He got his first job at 12, as a stock boy at a local bar. He was paid with proceeds of recyclable beer bottles he'd round up and return to vendors on weekends.

His father kindled Carpenter's passion for investing. The two of them would pore over Value Line's analyses of public companies. Whenever Phil saved up $1,000, they'd assemble a list of promising stocks; the final choice was Phil's. The teen schooled himself in the ABCs of stockpicking: valuations, margins, market share, barriers to entry, proprietary technologies. His first stock was Essex Chemical Corp., which made liners for chemical-waste dumps. He more than doubled his money when Dow Chemical Co. bought Essex in 1988. He was hooked.

Carpenter's career came full circle in 2002, when he joined Bear Stearns Merchant Banking, which John Howard had launched in 1997. His first gig had been as an analyst at Bear, Stearns & Co., which hired him in 1994 straight out of college, at Binghamton University, SUNY. He later worked six years for two buyout boutiques in Florida, Trivest Partners LP and Brockway Moran & Partners Inc., before returning to New York. (After Bear Stearns' collapse in March 2008, BSMB was reborn as Irving Place.)

The Chesapeake deal had its roots in BSMB's decision, urged by Carpenter, to zero in on packaging: "It was a large industry, $100 billion in the U.S. Almost every end market uses packaging, and some of those end markets have very good dynamics, like pharmaceuticals. Branded companies were allocating more money to packaging to make their products more appealing to the consumer."

The fragmented industry also lent itself to a buy-and-build strategy. Carpenter liked its steady growth. "I wasn't looking for the next Intel, just day-to-day consistent results," he says.

In 2007, Carpenter hired as a senior adviser Phil Yates, the ex-chairman and CEO of Graham Packaging Co. He calls Yates "my partner in building the packaging practice." His first deal in the sector was the 2004 acquisition of John Henry Co., a pharma packager, which he has expanded through six add-ons into a $500 million business called Multi Packaging Solutions Inc.

That deal was conventional. Chesapeake was anything but. It was a publicly traded, Virginia-based company with the No. 1 market share in pharma packaging in Europe and strong positions in Scotch whiskey cartons and high-end-chocolate boxes. It also was hamstrung with $550 million of debt and high operating costs, and its cash flows and stock price had eroded. Carpenter held talks with Chesapeake in early 2007 about a deleveraging take-private. No deal ensued, but he kept Chesapeake in his sights.

The talks revived in late 2007 as Chesapeake's health worsened. Under the circumstances, Carpenter thought it smart to pool resources with Oaktree Capital Management LP, a Los Angeles PE player that owned a European packager and had a track record in turnarounds. He hooked up with Jordon Kruse, a 30-something dealmaker at Oaktree, and the two began to stalk Chesapeake together.

In the spring of 2008, Carpenter and Kruse snapped up more than $100 million in face value of Chesapeake's bonds at pennies on the dollar. In December, Chesapeake filed for Chapter 11, and the bankruptcy court staged an auction in which IPC and Oaktree were the only bidders.

Though the bonds were wiped out, Carpenter says he had no regrets because the bond purchase enabled IPC and Oaktree to shape the outcome. The workout eliminated Chesapeake's debt; its only leverage is a roughly $100 million pension obligation.

To lead Chesapeake, Carpenter and Kruse brought in Jerry Kerins, who founded and built Continental Pet Technologies Inc.

Now, says Carpenter, the hard work -- as well as the real fun -- begins.