11/11/2009 11:59 AM ET
Conflict of interest: Yanks, Boras intersect
Team has decisions in left field and at DH
By Tom Boorstein / SNY.tv
Johnny Damon, enjoying a celebration with Nick Swisher, probably won't give the Yankees a discount. (AP)

Agent Scott Boras catches a lot of flak, much of it undeserved. Yes, he is a gasbag. But if his job is to get his players the most money, why shouldn't he try his hardest to do that? He doesn't have to look good in the process, and he usually doesn't. But he does look good to his clients, and that's what matters.

All the sanctimony about Boras' negative effects on the game gets in the way of a more serious discussion. How does he resolve the conflicts of interest that inevitably arise from his representation of multiple players?

The Yankees could be at the center of one of these conflicts. Their left fielder, Johnny Damon, is a free agent, as is a possible replacement, Matt Holliday. Boras represents both. With their deep pockets, the Yankees could represent the biggest financial opportunity for each of these players, but, at most, they will sign only one.

Doesn't that put Boras in a sticky situation? He could manipulate things to serve one client over the other. Suppose Boras makes Damon's price to the Yankees artificially high in an effort to make Holliday, who will sign a longer and bigger deal by virtue of his age, more appealing. Or Damon may want to return to New York enough to accept a discount. Boras could ignore this wish in his negotiations in order to help Holliday's chances of a Yankees payday.

Those are only some of the examples. When working for one client on an open market, Boras is the best. No one doubts that. But how does he resolve these conflicts when working for two clients simultaneously? No one knows.

As for left field: Few people thought Damon would be worth the four-year deal he signed with the Yankees before the 2006 season. Even when factoring in his unplanned but unsurprising move from center to left field, Damon earned the $52 million the Yankees paid him. That doesn't mean he's worth another expensive deal, even if it is for only two years.

Throughout the season, we heard, "Damon has the perfect swing for Yankee Stadium." That may be a euphemism for "His home and away splits are a little frightening." Damon hit .279/.382/.533 at home but only .284/.349/.446 on the road. Maybe his skillset is particularly suited to Yankee Stadium, but maybe he, as most of the team did, took advantage of the hitter-friendly dimensions.

Damon will probably cost at least $20 million over two years to keep. He has been durable as far as staying on the field. That doesn't mean he's been 100 percent whenever he has played. We hear all about his double steal in Game 4 of the World Series, yet his leaving Game 6 with a strained calf goes unmentioned. Damon will likely spend time on the disabled list in the next two seasons, and he's at an age where that stay (stays?) may be more than the minimum 15 days.

Of course, $20 million is the floor, not the ceiling for Damon. Boras clients rarely give discounts. As Jason Bay has said this offseason, "At some point, it is about the money." Don't expect anything different from Damon.

What are the Yankees' options? Playing Melky Cabrera in left and Brett Gardner in center field would help in center but kill them in left, as Cabrera doesn't have the bat to carry the position. Austin Jackson isn't ready to provide center-field offense at the big league level, much less left-field offense. Mike Cameron could be a cheap one-year fix. He's no spring chicken, and may not hit well enough to play left field, either.

Xavier Nady VI sprayed Champagne in the clubhouse and came to the Yankees' parade. Maybe he wants to come back. At the right price, he also could be a cheap fix. He's not as good as everyone thinks he is, but that doesn't mean he's terrible. With Teixeira and Alex Rodriguez ready to carry the load, all he'd have to do is blend in.

Holliday has an excellent National League track record, but he did have a mediocre stint in Oakland before being traded in July. On the other hand, that's a small sample size from a pitcher-friendly park. Boras loves to compare Holliday to Mark Teixeira, but Holliday isn't as good a hitter or as good a bet to contribute for the life of the contract he will end up signing. The Yankees don't need to take that risk.

The left-field decision isn't easy because there isn't a great answer out there. If the Yankees can extract a reasonable deal from Damon, they should do it. If not, they should probably sit tight in the Holliday sweepstakes and get creative.

Designated assignment: Besides Damon, the Yankees must also make a decision on Hideki Matsui. Matsui's home-road splits are similar to Damon's, except the full-time designated hitter did his best work on the road (.265/.354/.462 at home vs. .286/.383/.567 on the road.) He can still hit. That is unequivocal. The Yankees' concern rests in his hogging the DH spot. Suppose they need Jorge Posada to catch less over the final two years of his contract? "Roster flexibility" has been tossed around as a reason Matsui may be jettisoned.

Allow Bronx Cheer to make the case for Matsui to stay. The man is a rockstar in Japan and attracts a huge following among the Japanese press. That has to be good for overseas marketing. Second, if Matsui has to head to the bench to accommodate Posada, that isn't a problem. The Yankees, the team that once chose Doug Mientkiewicz over Carlos Pena and had Cody Ransom as its Opening Day third baseman, are suddenly experts on how to use the back of their bench? Matsui will probably be cheaper than Damon, and he's a better hitter, even relative to his position. His value takes a hit if he has to make way for Posada at DH, but it can be recouped, at least in part, by the continued exposure he gives the Yankees in an overseas market.

The Yankees' offense is due for a letdown next season. Age-defying years won't be repeated. Overspending won't change that. The Yankees would be better off concentrating their resources on the less obvious answers and other issues facing the team, namely a shallow starting rotation. But that's a story for another day.

Tom Boorstein is the lead editorial producer for SNY.tv. Follow him on Twitter at http://www.twitter.com/MLBoorstein.
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