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Theo's winter of discontent

Jeff Passan
Yahoo Sports

Well, so much for that grace period the Boston Red Sox appeared to buy themselves with a championship. Theo Epstein can laugh about this now because after the drama of the past year – his sabbatical, his re-anointing as general manager and the Red Sox's dissolving like a pot of boiling water in the second half – some gallows humor is good for humility.

"I think that lasted for about a week," Epstein said from his Fenway Park office Wednesday. "And I think it's great. It shows that fans really care about the team. There's no greater place to be when we're winning – and no worse place to be when we're losing."

Stepping on the plank comes with the job of Red Sox GM, where the noose is always tied and waiting to be fitted. These days, Epstein stands there not knock-kneed but with the preternatural poise – and confidence that can bleed into arrogance – needed to succeed, with the Red Sox's involvement in so many potential transactions he'd need an octopus' arms to juggle them all, and with the knowledge that this offseason, as much as the 2004 World Series title, could define his career.

Where to start? Is it with Daisuke Matsuzaka, the Japanese right-hander who has never thrown a pitch in the major leagues and whom Epstein and his lieutenants deemed worth $51.1 million for negotiating rights alone? Is it with Manny Ramirez, the best pure hitter in baseball this side of Albert Pujols and whom Epstein is dangling to any team willing to trade prospects and take on his antics? Is it with J.D. Drew – talent unquestioned but ability to thrive in Boston just the opposite – who's on the verge of signing a megabucks deal to play right field? Or is it with Roger Clemens, whose return to Boston for one final hurrah would bring a nice bit of symmetry to his career and give the Red Sox the best rotation in baseball?

Epstein, for one, plays down the gravity of this offseason, claiming it's just like any other, saying that "when you're in the office trying to negotiate a contract, it's just part of the job. We've got a whole team working on things here."

Maybe so, but the glory or the guff will go to Epstein, and after his power play asserted him more control over the franchise's direction, he heads into next week's winter meetings poised to shake them – and the Red Sox – up.

Already Boston made the move of the winter with the posting bid for Matsuzaka, which, as the pitching market shakes itself out, is looking somewhat reasonable. Adam Eaton, who has never posted an earned-run average under 4.08 or thrown 200 innings in a season, got $24 million for three years from Philadelphia. Jeff Suppan is poised to get $10 million a year, Barry Zito perhaps $17 million. And the New York Yankees, the team that bid only $32 million for Matsuzaka, landed the negotiating rights to left-hander Kei Igawa – a pitcher most executives envision as a No. 4 starter – for $26 million.

"It's a challenging marketplace," Epstein said, and keep in mind this comes from someone whose payroll could creep toward the $148 million luxury-tax threshold.

It's one in which Ramirez, who is owed $38 million over the final two years of his deal, seems a relative bargain, and one in which Drew can opt out of a contract that guarantees him $33 million over three years and back into one that reportedly will pay him $70 million for five. Lord knows what Clemens could fetch for a full year. Anything less than $20 million would seem downright miserly.

Epstein's job, in such a bull market, is simply to hold on for eight seconds and hope he doesn't get gored. Part of the luxury of being a have is the ability to screw up. If the Red Sox sign Julio Lugo to play shortstop and he turns out to be the second coming of Edgar Renteria, there is always a team willing to take a bust at a bargain price. If Hideki Okajima, a Japanese reliever signed to a two-year deal Thursday, happens to fail, hey, he's just a middle man.

At the same time, the magnifying glass is trained even closer on Epstein, and each of these moves is a sunbeam, ready to fry him like an ant. Once the Red Sox and Matsuzaka's agent, Scott Boras, hone in on a deal – the guess is four years and between $40 million and $50 million, with the Red Sox reportedly starting around $8 million a year and Boras asking for $15 million – they will have committed $100 million to the procurement of a player who could be homesick … or whose pitches might not translate … or who knows what else. With a Dec. 14 deadline to finish a deal and the posting money returned to the Red Sox if they can't come to one, the Matsuzaka bet is a good one. It's just risky.

Similar to almost everything else Epstein has entertained since the season ended with the Red Sox in third place in the AL East. It was Boston's worst finish since Epstein took the reins on Nov. 25, 2002. Only 28, he was a good story: youngest GM ever, grew up in the shadows of Fenway, a Yalie personifying baseball's new breed. Now he's 32, hardened by his bad experiences first, then his team's.

"It happens," Epstein said. "We were the second-best team in baseball in the first half of the season. We were playing great, pitching well, playing great defense, getting on base at a high clip. We really hit a rut and came down with a bunch of injuries. No excuses.

"We didn't do a good enough job. I didn't do a good enough job. You don't make the playoffs every year. It's more important what you do to respond to it. … Because we got our butts kicked. It's not the last time it'll happen."

Realism is an ally of the risk-taker. Epstein understands how low the downs can get, how all of the good forged by the championship could be smudged by a few more tough years, how important it is to thrive.

It's something he experienced before, and something he's banking on the Red Sox doing again.

"Don't forget," he said, "we've done our share of butt-kicking, too."