Business of Scott Boras unfinished

While Joe Torre embraces the next chapter of his life at age 71, Ryan Braun awaits resolution of his drug-testing appeal and Hall of Fame candidates sweat out Monday's big Cooperstown announcement, Major League Baseball is entering the final phase of the Hot Stove season. For want of a better term, we'll call it the Scott Boras Olympics.

Of the top 20 free agents on Keith Law's best 50 this winter, eight are still unsigned. Four of them -- Prince Fielder, Edwin Jackson, Ryan Madson and Carlos Pena -- are represented by the Boras group.

A lot of agents might get antsy sitting on so much high-priced talent after New Year's Day, but Boras projects an air of calm born of past experiences and great escapes. He points out that Matt Holliday signed a seven-year, $120 million contract with St. Louis in January two years ago, and Pudge Rodriguez and Magglio Ordonez both landed in Detroit in February several years before that. Heck, in 2004, an aging Greg Maddux waited until March 23 before signing with the Cubs. He went 16-11 and pitched until he was 42.

In Boras' world view, the trade market is almost tapped out, the non-tenders have been picked over and teams are seriously assessing their rosters and coming to the realization that they still have holes to fill and a need to act before spring training.

"The January free-agent lifeboat is a welcome addition to prevent next season's Titanic," Boras told ESPN.com.

Boras has been long on colorful quotes this offseason, if not action. He has compared Fielder to Warren Sapp for his agility and called him a hybrid of Frank Howard and Henry Kissinger for his rare combination of power in the batter's box and diplomatic skill in the clubhouse. In an interview with Adam Kilgore of the Washington Post, Boras addressed speculation that the market for Fielder is a tad slow with the assurance, "There's a lot of passengers on the PF Flyer."

The dynamic for big-name free agents has been a little strange this winter, for sure. While the Marlins and Angels have spent gobs of money, the Red Sox and Yankees have been uncharacteristically restrained. The Dodgers are for sale, the Mets non-factors, the White Sox are retrenching and the Cubs' approach is still evolving under the new management team of Theo Epstein and Jed Hoyer.

Agent Dan Lozano has negotiated more than $300 million in guaranteed money for clients Albert Pujols, Carlos Beltran and Jimmy Rollins, and Seth and Sam Levinson of ACES attacked the closer market with multiyear deals for Jonathan Papelbon and Heath Bell. But outside of Francisco Rodriguez, Willie Bloomquist, Bruce Chen, Andruw Jones and Andrew Brackman, Boras' clients are still waiting to learn their 2012 destinations. He has a reputation for slow-playing the market, but could this be the winter that he's waited too long?

"He's the best for a reason," said a National League executive. "You have to marvel at his smarts and all that. But eventually, if you don't change the plays, the defense stops you. And he keeps running the same plays."

Said one fellow agent, "Some of his guys are going to be [in trouble] because there are only so many hours in a day."

Amid the skepticism, history shows that Boras is likely to negotiate a forehead-slapping deal that no one envisioned. Let's reflect upon last winter, when the Yankees signed reliever Rafael Soriano to a three-year, $35 million contract (with opt-out clauses) on Jan. 18.

"As a player, I would think you would want to know where you're headed," said an NL executive. "If it were me, I would be feeling pretty uncomfortable right now. But who knows? The amazing thing is, somehow he always seems to get them the money."

Boras has a proven ability to negotiate big contracts amid a climate of doubt, but is he trapped in a box he can't escape this time? We'll learn the answer soon enough based on what happens with his All-Star clientele:

Prince Fielder

Yes, the process has been deliberate, but Boras claims it's because so few free agents have amassed such a stunning résumé at such an early age. Owners are talking to Fielder, Fielder is getting a feel for owners, and the process is shrouded in mystery. Boras even declines to confirm meetings with specific clubs because he has a standing pledge to owners to keep things confidential.

"In these kinds of negotiations, no one wants to finish second," he said.

So who'll finish first on Prince? You can't count out the Cubs. But the available evidence suggests they're engaged in a full-fledged, ground-floor rebuild that began with the trade of reliever Sean Marshall to Cincinnati and continued when they sent Carlos Zambrano packing to Miami. The consensus is that Epstein and Hoyer have done their homework and are lingering on the fringe of the Fielder sweepstakes, and that new manager Dale Sveum truly does have a fondness for Prince. But the Cubs aren't going to do something exorbitant just to energize the fan base.

True, Boras is adept at cultivating ownership, but it's hard to envision Cubs chairman Tom Ricketts big-footing Epstein this quickly and spending $250 million or more on Fielder when his chief baseball man doesn't think that investment jibes with the long-range plan.

"I think Theo will let Fielder come to him, but he's not going to beat the market on him," said another general manager. "He's not going to win a bidding war. It just doesn't fit into the long-term plan they're putting together."

Most of the recent buzz has come from Washington, where Boras has an established rapport with the Lerner family and general manager Mike Rizzo. Texas isn't out of the picture entirely, but right now the Rangers' energies are focused on signing Yu Darvish by the Jan. 18 deadline.

One big league GM calls Seattle a "darkhorse" for Fielder or one of the other Boras clients, even though Mariners general manager Jack Zduriencik has publicly downplayed the team's pursuit of Prince.

"There's some pressure on Jack to do something to counteract what the Angels and Texas are doing," the GM said. "They're kind of lying in the weeds."

Ryan Madson

Madson was close to re-signing with Philadelphia when talks broke down and the Phillies turned to Papelbon on a four-year, $50 million deal. Since then, Madson's market has been undercut at every turn. The Padres (Huston Street), Blue Jays (Sergio Santos) and Red Sox (Andrew Bailey and Mark Melancon) filled their closer voids through trades, and Joe Nathan, Frank Francisco and Matt Capps found new homes on one- or two-year deals.

The Reds are still shopping for a closer, but they've barely discussed Madson and seem more inclined to bring back Francisco Cordero. Toronto GM Alex Anthopoulos has shown no inclination to pour big money into the back end of his bullpen.

In an email Thursday, Angels GM Jerry Dipoto told ESPN.com that he doesn't plan to pursue to Madson.

"Presently, our focus is on creating depth and different looks as it pertains to getting the last nine outs of a game," Dipoto said. "We will always look to be opportunistic, but at this time it is unlikely that we will be a significant player for Madson."

Some baseball insiders suggest that Madson might be best served signing a one-year deal and going back on the market next winter when fresh opportunities await. Jose Valverde is in the final year of his deal with Detroit, Mariano Rivera has to retire one of these years, and by next winter the Red Sox might have concluded that they're ready to spend money on a closer.

Madson has a total of 52 big league saves and one full season in the role, but Boras is pitching him as the answer for a contending team in need.

"He's at the entry-level age where elite closers really start to become successful, and that's 30," Boras said. "The great closers all have a secondary pitch to support their velocity, and Ryan has the fastball-changeup combination. He's demonstrated his ability in a playoff environment, in a major city, in an offensive ballpark. He has all the central dynamics for success as a closer -- on a championship team."

The Phillies are still waiting for an update on the health of Jose Contreras, and one NL official suggests Philadelphia could be a nice "security blanket" for Madson on a one-year deal as a setup man -- although it's hard to imagine he would be thrilled with that arrangement. It's also late enough in the winter that GM Ruben Amaro Jr. might have to make a corresponding move to free up payroll, and no one in Philadelphia seems particularly interested in that scenario.

Edwin Jackson

Boras' agency churned out a 73-page binder in homage to Fielder, but that might not qualify as his most ambitious piece of handiwork this offseason. He also sent general managers a 56-page Edwin Jackson booklet that might help them forget (almost) that Jackson is a career 60-60 with a 4.46 ERA.

The Jackson book has exhibits comparing him to Wilson, Mark Buehrle, Cole Hamels, Josh Beckett, A.J. Burnett, John Lackey and Derek Lowe, even though some of those long-term contracts haven't panned out very well. It touts Jackson for his hitting ability, his character and his durability on the mound.

In the "Starting Pitchers: Age 27 & Under" segment, you'll find this interesting nugget (see table):

"Over the past 5 seasons (2007-2011), Edwin Jackson is one of only 5 pitchers age 27 or younger with 950 or more IP and an ERA under 4.35."

Compare the ERAs -- and take note of the fact that Jackson has already pitched for six teams -- and you'll understand why some executives are dubious.

"He's not a great pitcher. He's a good pitcher who's been really healthy, and there's value in that," said an AL general manager. "It's kind of a niche. It has to be a team that needs a reliable, healthy, middle-of-the-rotation guy and is willing to pay a premium for him. But not many teams fit that description."

Jackson's price tag is giving teams pause. ESPNNewYork.com's Wallace Matthews reported that Jackson is seeking a five-year, $60 million contract. But Boras is pushing the fact that Jackson is 4½ years younger than Buehrle, who just signed a four-year, $58 million deal with Miami. If anything, that five-year, $60 million report might be on the light side.

How willing are teams to give Jackson $15 million annually when Roy Oswalt is available on a one-year contract, Hiroki Kuroda is looking at something short-term and Joe Saunders is out there for the taking? Boras has his work cut out for him with this one.

"Say what you want about Mark Buehrle's stuff, but he has a proven track record," said an NL talent evaluator. "I like Edwin, but he's a high-pitch-count guy who can be Jekyll and Hyde with his command. He'll give you 200 innings, but it's a laboring 200 innings."

Carlos Pena

When the MLBTraderumors.com website asked its readers, "Which team will sign Carlos Pena?" a whopping 10 teams received votes from 15,500 respondents. Milwaukee was first at 19.7 percent, the Cubs were second at 12.7 percent, and Tampa Bay, Toronto, Pittsburgh, Baltimore and Cleveland all hovered in the 7 percent to 9 percent range.

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Carlos Pena


The Brewers make some sense at face value, given that Fielder is leaving town, but the economics probably don't work. GM Doug Melvin already stretched his budget when he brought back K-Rod as a $13 million setup man and signed Aramis Ramirez to a three-year, $36 million deal.

Even though the Cubs are penciling in 29-year-old Bryan LaHair at first base, some baseball people think Chicago could fit for Pena on a short-term deal. Pena hit 28 homers with a .357 OBP for the Cubs last season and won't clog up the position long-term in the event the Cubs decide to make a run at San Diego's Anthony Rizzo, the former Boston prospect who is now stuck behind Yonder Alonso and Jesus Guzman in the Padres' first base pecking order.

The old standbys

Boras clients Johnny Damon, Pudge Rodriguez, Jason Varitek and Magglio Ordonez are still out there. So are Rick Ankiel, Alex Cora, Kevin Millwood, Mike Gonzalez, Ryan Spilborghs and Xavier Nady. And there's a smidge of a chance J.D. Drew will play in 2012, although he appears to be leaning toward retirement.

All these players have something in common with Fielder: They're still looking for jobs, and their agent doesn't seem worried about running out of time before pitchers and catchers report.

"You just don't put timetables on talent," Boras said. "When you're not offering contracts, you don't have any control over the dynamic. You've got to wait for the ball to get over the plate. It's like playing the game. You have to be patient and ready."

Boras has never been short on patience -- or confidence. But with New Year's Day in the rearview mirror and Groundhog Day on the horizon, he has a lot of players still waiting for that January lifeboat to arrive.

Jerry Crasnick is a senior writer for ESPN.com. Click here to purchase a copy of his book, "License to Deal," published by Rodale. Crasnick can be reached via email.

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