ESPN Buster Olney Blog

Matt Holliday is set to become a free agent in the fall, and Oakland will not re-sign him. For the Athletics, a team with a modest payroll, an investment of 25-30 percent of their resources in one player is high risk, something they've always avoided. (See Zito, Barry; see Hudson, Tim; see Mulder, Mark; see Tejada, Miguel). And historically, the teams that have devoted a high percentage of their payroll usually wind up regretting it (see Rockies, Colorado, re: Todd Helton).

So regardless of whether Oakland trades Holliday to a contender at midseason or keeps him for itself all summer, he'll be the CC Sabathia of the next free agent market, the most coveted player available.

As with Mark Teixeira, however, the number of teams that will actually pursue Holliday figures to be limited, and perhaps reduced by the wave of economic difficulty that many teams are seeing on the horizon.

Holliday would be a great fit for the St. Louis Cardinals, for example, because he could be a complement for Albert Pujols, hitting in front of him or behind him. But this might be the first year since the early part of the decade the Cardinals don't reach 3 million in attendance.

The addition of Holliday would give the Mets tremendous right-left balance, but New York appears to be veering away from its free-spending days of Pedro Martinez and Carlos Beltran, and are ready to rely more on in-house products like Daniel Murphy (who continues to impress the staff greatly).

If Manny Ramirez remains with the Dodgers for 2009, they won't have the flexibility to pursue Holliday, and the Cubs have multiyear investments in Alfonso Soriano and Milton Bradley, making it unlikely that they'll get involved.

And the bidding on Holliday may well be impacted by an industry-wide shift away from spending on players in their 30s. Holliday turns 30 next winter; assuming he were to land a five-year contract, he would be 35 in the final year of the deal. Teixeira got an eight-year, $180 million contract at age 29, as a Gold Glove-caliber first baseman. Holliday is a corner outfielder who is generally viewed as slightly below average defensively.

But among the few teams that pursue him, the offers will likely be robust, because he is one of the game's elite hitters, having posted a career OPS of .938. There are some questions about how great his production will be now that he has left Coors Field, but a lot of talent evaluators don't believe he's part of that Vinny Castilla Club. "He hits the ball hard a lot, and that won't be affected by where he plays," said one general manager.

An early line on the upcoming Holliday season:

1. ANGELS: Vladimir Guerrero has done exceptional work for the Angels, but he will be eligible for free agency after this year, and at age 35, there are distinct signs of regression in how he moves and how he hits. It may be that the Angels will work out a deal to bring him back.

But Holliday would represent an easy alternative, and his work and team ethic is right in line with the preferences of manager Mike Scioscia. The Angels will probably have the need for somebody like Holliday, and they'll probably have the money.

The X factor is the club's relationship with Scott Boras, who represents Holliday; whether or not that will be an impediment remains to be seen.

2. RED SOX: They are a team in need of an infusion of power for the middle of their lineup, which is why they were aggressive in their pursuit of Teixeira. Even if David Ortiz, J.D. Drew and Mike Lowell all hit well in 2009, they have all reached the stage of their respective careers when their projected production will be in question. And Jason Bay, who will be 31 in the fall, will be eligible for free agency.

Holliday would probably love hitting in Fenway, and he knows firsthand of the adrenaline kick received from playing in Boston, after experiencing the 2007 World Series. In a world without complications, the Red Sox would probably love to have him, and he'd probably love to play in Boston.

But it remains to be seen how the Teixeira negotiations have affected the relationship between the Red Sox and Boras, and there is no doubt about this: The Boston front office was livid about how those talks played out.

Once again, the Red Sox will likely be competing against the Yankees for the player.

3. YANKEES: The contracts of Johnny Damon and Hideki Matsui will expire after this season, so the Yankees will be in a position to take a run at Holliday -- and if the team doesn't make the playoffs again, the Yankees will be under enormous pressure to sign the slugger. If you think the right-handed hitting Holliday wouldn't be a good fit in Yankee Stadium, well, there are long-term scouts who would vehemently disagree with you.

"You know how [Derek] Jeter flips his home runs over the right-field wall?" asked one scout. "That's exactly how Holliday would hit in Yankee Stadium, except in much greater volume. His swing is perfect for Yankee Stadium."

Jeter might be the X factor. At some point over the next 18 months, the Yankees may well approach him about shifting away from shortstop. He cannot move to third base, because of Alex Rodriguez, and Teixeira is locked in as the first baseman for the next eight years. It's unlikely the Yankees would consider moving Jeter to second base, because the questions about whether he would have suitable range to play the middle infield will still stand.

So if Jeter is to continue playing with the Yankees, it would probably have to be in left or right field, given that he will turn 36 in June 2010. That looming issue shouldn't be a consideration as the Yankees think of ways to improve for next season, but the reality is that political concerns were at the root of the club's decisions to essentially overpay Mariano Rivera, Jorge Posada and A-Rod in the winter of 2007-08.

4. WHITE SOX: Jermaine Dye and Jim Thome may well be entering their final seasons with the White Sox, and Paul Konerko's contract will expire after 2010, which means that the team will need a thumper amid all the young, athletic players they are collecting. Holliday would fit, in many respects.

But the White Sox have not had a lot of Boras clients on their roster through the years, and that's not by accident.