Houston Astros vs St. Louis Cardinals

Like most teams, the Boston Red Sox offseason will be defined by the willingness of their owner to open his wallet.

Fortunately for Sox fans nationwide, Uncle John certainly has some deep pockets. However, the amount he is willing to spend will have a lot to say about the direction that this team will be headed.

The prudent move by the Red Sox will be to look for incremental gains in what is partly a  transitional year, while also being a year of opportunity. The club has nearly its entire 2009 starting lineup under contract, including its entire starting staff and at least seven of nine position players. For a team that won 95 games last season, that’s a recipe for success. Still, the American League gets more competitive every year, as the AL West, the Yankees, and our little brother Rays make it harder and harder to buy the Wild Card.

With a lot of money coming off the books after 2011 and a good core set up for 2010, Theo needs to opt for short-term deals this off-season. The team has a chance to make a huge impact in 2010 and 2011, so they should conserve while they can but still have some risk built into their plan.

But man, does that Julio Lugo signing handicap this winter of ’09. The Sox are, in essence, paying the Cardinals to play the failed shortstop, who is owed $9.25 million. Luckily, that obligation ends after this season. Ortiz’s services, at the cost of $13 million this season and a 2011 club option, as well as Mike Lowell’s obligations also come off the books after next season. In all, the Sox have just $49.3 million tied up in 2010 contracts, though that figure is sans Beckett, V-Mart, any 2009 free agents or arbitration cases yet to be decided.

Still, it’s a good position to be in when (potentially) Joe Mauer, Victor Martinez, Carl Crawford, Brandon Webb, Roy Halladay, Josh Beckett, Cliff Lee, and Javier Vazquez all hit free agency.

But there’s more to a team than waiting for a free agent period over a year away. After all, too much planning for the future can be a bad thing. Maybe the New York Knicks will teach us all a valuable lesson when LeBron doesn’t head to the Big Apple after all that planning and hoping involved.

As a result, the Sox need to think about this season, as they’re in great position to improve upon a team that, for all intents and purposes, should be going through a rebuilding phase. They have two expensive, expiring contracts on the books for declining players (Lowell, Ortiz) and an aging captain in Varitek. That is usually a disastrous recipe. However, the Sox have weathered the storm with few hiccups.

Now, with the stage set, let’s get on with the 2009 off-season blueprint.

Kiss Bay Good-Bye, Sign Matt Holliday

This should be priority number one of the off-season. Though Bay is the best hitter and run-producer on the free agent market, Holliday is the better all-around player and lower risk of the two left fielders.

Holliday has a number of advantages over Jason Bay that make him the better candidate, especially when considering both players are certain to get long-term contracts.

First, he is the better fielder. While Bay was doing his best to embarrass himself out by the Green Monster (-8.7 UZR/150), Holliday was posting an above-average defensive year (3.2 UZR/150). This difference is critical when considering the merits of the two players. When picking between two similarly valued assets, it is always smart to minimize risk. In baseball, the primary way of doing this is to find the player who diversifies their value better – typically players who can hit and field.

Since predicting an off-year with the bat is never an easy chore, we should seek to find a player who can fall back on their fielding abilities. Therefore, Holliday has the lower floor because it is unlikely that both his hitting and fielding will decline in any one particular year, meaning that if one should decline, he will retain value in the other. Bay does not have this luxury: as his hitting goes, so does his overall value. He does not have defense to lean on in a poor year with the stick.

But the comparison does not end there.

Bay is going through what seems to be a strange transition as a hitter. Bay’s most important attributes are still alive and well. He has tremendous power and a good eye at the plate, drawing plenty of walks. However, this season, his strikeout problems began to get out of hand.

Bay’s sudden drop in contact rate (77.1% in 2008; 71.7% in 2009) casts some doubt as to whether or not he will age well at the plate. Should his rates rebound, he will age gracefully. If not, this could get ugly in a hurry, as it’s not out of the question that his strikeouts could approach 35% of his at-bats. This is akin to a doomsday scenario, dropping his batting average into the .250s and below.

It should be noted that this is not at all the rule of player progression and that it is possible that his contact rates could improve – but it is a scenario that must be weighed against potential alternatives.

Since Bay’s future is largely dependent on his contact rate and a four-plus year contract that could stretch into his age-35 season and beyond, he’s not the safest bet by any means.

But Holliday is not without risks of his own. For instance, his 2009 line is very much dependent on a high batting average on balls in play (BABIP) which is not easy to reproduce, at .346. This, coupled with his past as a Rockie, would lead one to believe that Holliday should be headed for a downturn. It would be good to temper enthusiasm somewhat, as high BABIPs are never a good thing to bet on; though, he has been consistently good throughout his career. In addition, Holliday’s contact rates are less than ideal, which means he may have more problems with strikeouts in the future than he has let on thus far.

But getting back to Holliday’s past as a Rockie, there are reasons to believe he is not quite the Colorado aberration many make him out to be. Holliday’s home/road splits as a member of the Rockies are grossly overexaggerated. His three-year road numbers from 2006-2008 were .296/.370/.486, which are good (though not great) numbers. Still, with his .313/.394/.515 line this season between Oakland and St. Louis, he doesn’t seem like the Coors product that other players have been in the past.

In essence, the advantage of Holliday over Bay is getting the less risky asset. Holliday is the better fielder, has fewer strikeout issues, and is a full year younger. While this may not seem like much, when talking about a player’s age-34 and 35 seasons, it becomes very important. With the salaries these two players are expected to earn and the expected lengths of the contracts, it is always prudent to go with the less risky option.

Holliday might not be the quality of hitter than Bay is, but when getting to that fourth year (or fifth, as some sources indicate), Holliday looks like the better play. Remember, it’s not always about getting the best player, it’s often about not getting the worst. As a result , the Sox should forego signing Jason Bay and make every effort to land Holliday instead.

Roll the Dice on Rich Harden

Here’s another interesting contract that could go south at any time. Harden has been pegged throughout his whole career as an injury case – and rightly so. However, with the quality of pitcher that Harden is and the Sox’ deep pockets, this seems like a good player to roll the dice on.

Harden is unique for both his talent and his health. Most pitchers have enough healthy seasons in their past that teams will bet that they can stay on the mound with some regularity. Harden doesn’t as everyone and their grandma knows that he won’t throw any more than 140-150 innings. Therefore, teams will value him accordingly and it will be harder to overprice him due to the “potential” to throw a full season.

Some sources are quoting as a high as 4/50-60 for Harden. Unless that contract comes down considerably and for 3 guaranteed years at most, this will be a bad deal for the Sox to make. His agent may want a deal like Derek Lowe’s last year (4/60) though the Sox shouldn’t  pay for it. Others have quoted 3 years /$30 million or Oliver Perez’s 3/$36. If the Sox can get that price, it might be a good idea to pull the trigger. This deal begins and ends with the contract length. If there’s a 2-year deal on the table, its an unequivocal yes.

Sign Shortstop Marco Scutaro

This one has had me tossing and turning for days now. With the price quotes falling somewhere in the 2-3 year, $8-$10 million dollar range, Scutaro could become quite the bargain for a free agent signing. His 2009 breakout was quite an intriguing one, as it was not fueled by anything that was necessarily all that fluky. He didn’t hit 20 home runs, he didn’t hit .350, he didn’t bat in 120 runs.

What he did do, however, was something much more surprising and perplexing. Marco Scutaro has always had a good eye at the plate, never swinging at more than 16.8 percent of pitches outside the zone since he became a semi-regular back in 2004. This past season, he set a career low at 12.3%.

What is particularly interesting about this, however, is that he completely altered his swing frequency at the plate, offering at just 34.5 percent of pitches – a strikingly low number, more than 7 percent lower than his 2008 mark (41.6%).

Whether or not he can maintain this approach is anyone’s guess. While pitchers are sure to adjust and throw him more strikes, it might not make much difference. Even if they do, he has such good contact skills that it will only aid his strikeout rate, which will help his batting average.

Scutaro has some surprisingly good indicators for a player who has been a utility infielder his whole career and he deserves to cash in after his excellent 2009. While he may go for a longer deal, we’ll chalk him up as a Sox’ signing and give him two years, because we’re optimists.

A great fit for the team, he would go a long way at plugging up a whole that has eaten away at this franchise for years. A short deal for a player with moderate risk, he’ll avoid being the mistake that Julio Lugo or Edgar Renteria were merely by virtue of him having a shorter contract.

This could be quite the signing. Even though he isn’t guaranteed to repeat his 2009 success, he has such a unique skill-set that there’s not much reason to believe he can’t do it. An older player (34 years old) who’s game is built on an exceptional batting eye, excellent contact skills, and solid defense, his game should age well. He’ll be a great value for a team that desperately needs to improve at short. He could be the biggest upgrade of all three free agents.

Maintaining the Rest

Jason Varitek: The Sox should decline Varitek’s team option, letting him sign on as a $3 million backup. He doesn’t have much – or anything – left in the tank, so this is almost a courtesy. But, exercising the team option for $5 million would just be wasting money.

Tim Wakefield: Resigning Tim Wakefield, especially if the Sox sign Harden, is a no-brainer. Wakefield could pitch half the season and still be worth it. He offers so much stability and depth to this team at such a good price that they are almost obligated to re-sign him. Another gift from the elder statesman.

Maintaining the ‘pen: The Sox should be able to keep both Manny Delcarmen and Ramon Ramirez for 2010. Both are good young arms at a good price. However, Takashi Saito and Hideki Okajima present a unique problem. Resigning both may be problematic in this scenario where the Sox sign three free agents. As a result, we’ll say the Sox sign Okajima, the lefty, and let Saito go. Billy Wagner may have to go, as well, under this scenario, which is a tough pill to swallow. However, the reliever wants to close, so with Papelbon and Bard still in the picture, it’s an easier decision to make.

-Buyout Alex Gonzalez’s option: This one is unfortunate, as A-Gon was so good for the team when they needed a stopgap. However, we’re committing to Marco Scutaro, so that leaves no room for a $6 million backup. The Sox are strapped for cash under this scenario, so there’s just no money for his option. Sorry old fella.

2010 Starting Roster

C Victor Martinez

1B Kevin Youkilis

2B Dustin Pedroia

3B Mike Lowell

SS Marco Scutaro

LF Matt Holliday

CF Jacoby Ellsbury

RF JD Drew

DH David Ortiz

SP1 Josh Beckett

SP2 Jon Lester

SP3 Clay Buchholz

SP4 Rich Harden

SP5 Daisuke Matsuzaka

SP6 Tim Wakefield

Certainly, signing three prime free agents would be a dream scenario and the Sox are in a position where they can take a couple risks. They may have to push the salary cap to a four-year high, but they also should have the resources to do so.

Under this scenario, they get one high-priced, incredibly talented, long-term commitment (Holliday), one moderate-to-high risk free agent at a moderate length (Harden, three years), and one moderate-to-low risk, short-term commitment (Scutaro).

These moves may cost the Sox around $35 million, so they won’t have much room left for other signings. However, these acquisitions will set them up for a great year in 2010 while the money coming off the books in 2011 leaves them in prime position to pursue marquee free agents next year.

I like the three free agent approach though I must say John Henry will have to pony up to make it all happen. However,  it will be money well spent as it will put the Sox in the thick of a pennant run in 2010. Either way, only time will tell which direction the club ultimately moves.