Spend now or spend later?

Tony Massarotti's latest article at the Boston Globe deals with the Sox payroll -- both short-term and long-term versions of it. It's something we've been exploring a bit here at Fire Brand, and Mazz does a great job tying it all together. I was planning on bringing up this subject in later articles, but I might as well now, given the money quote here:

The biggest question Epstein may be faced with this offseason will result if he fails to sign either Bay or Holliday, leaving the Sox with a fistful of money and no marquee free agents to spend it on. When that happened last year, Epstein signed a handful of pitchers to one-year contracts and rolled the dice that the Sox could pitch their way to a world title. And though that plan ultimately fell a few steps short, the Sox essentially are right back where they started. With a roll of cash in their pockets, faced with the decision of spending it now or spending even more later.

As I've alluded to, this free agent class is horrible when it comes to making significant investments on the free agent market. There is no clear "break the bank" player. Bay understands he isn't one, but is gunning for years, reportedly. Holliday is pretending he's one. So what is Theo to do? Break the bank now or later? The Sox attempted to do this last year with the signing of Mark Teixeira, but Theo's conservatism cost the BoSox big time -- and you can bet he realizes this. So, to reiterate: Do we spend now or later? You decide, but let me just point out potential 2011 free agents: Carlos Pena (who may cement himself as a major free agent target -- he's close), Julio Lugo (had to, just for kicks), Derek Jeter (hey, he wants to play for Boston), Adam Dunn, Jayson Werth, Josh Beckett (so we need to try and resign him), Roy Halladay, Huston Street and of course... Joe Mauer. So tell us. Spend now or later?

POLL: One person only

New Poll Question: If you could only have one player of the list, who would it be?

• Jason Bay
• Adrian Gonzalez
• Matt Holliday
• Felix Hernandez
• John Lackey

What if it comes down to one person? Who would you opt for? Vote in the poll on the sidebar.

Wakefield, Hoyer, and Squinting at Free Agents

Wake Undergoes Surgery Tim Wakefield underwent surgery Wednesday to repair a herniated disk and loose bone fragment in his back. Wakefield is expected to pitch next year and should be ready for Spring Training. The 43 year-old vet was visually hampered last year, turning in a 4.58 ERA and 4.58 FIP despite his woeful last three starts (14 IP, 14 ER, 8 K, 12 BB). Squinting at Free Agents While we have gone at length discussing the top free agents and mapping out blueprints for the Sox’ offseason, there are a number of intriguing names on the market that are flying under the radar. Not all of them are the safest bets, with varying levels of performance or injury history, but they do have some sex appeal. Here are a few names to mull over. Special thanks to Eddie Bajek of MLB Trade Rumors. OF Rick Ankiel: Ankiel came off a sub-par season in 2009, as his power was down, his walks were down, and his K’s were up en route to a .231/.285/.387 line.

Assessing Boston’s other left field candidates

Jason Bay. Matt Holliday. Jason Bay. Matt Holliday. Matt Holliday. Jason Bay. Jason Bay. Matt Holliday. Matt Holliday. Jason Bay. Okay, let's take a break from the two obvious left-fielder candidates and focus on other free agents that could be manning left field for the Red Sox in 2010. I'm thinking that Theo's going to give this club another run with a fill-in left-fielder because as comprised, the team is still very good. As comprised, the team can still hit 95 wins -- if things go right. To compete in a transition year, however, we're going to need a left-fielder that can produce.

Bowden and Reddick’s Place in the Master Plan

Two of the Red Sox' biggest prospects, Michael Bowden and Josh Reddick, had less than stellar seasons in 2009. While the pair still remain tremendous talents, it has now become more difficult to see either one in the Sox' future plans, due in part to their failures this year as well as the team's changing circumstances. Still, should either or both pan out as originally expected, they would be quite the addition to a team in need of an infusion of cheap, young talent. Michael Bowden It’s hard to say that Bowden is at a crossroads in his career. He just turned 23, he possesses excellent stuff, and has been great in his minor league showings. However, his 2009 was nothing short of a disaster, as he was belted in every way imaginable in every appearance he made.

Coveroo TRIVIA: Honoring Cy Young

How was Cy Young honored in August 1908? (Two specific actions happened.)

Aroldis Chapman or Yusei Kikuchi: A fit with Boston?

Today, we're going to look at two rookie pitchers that are testing free agency. One is certain to join a major league team. The other... not so much. The former is Aroldis Chapman. Chapman is believed to be 21 and is a left-hander out of Cuba, defecting this past July. If you watched the WBC, you would have seen Chapman represent Cuba. There is no question that Chapman has electric stuff -- he holds the record for fastest pitch in Cuban history, being clocked at 2012. He's also been called one of the three greatest pitchers currently not in the major leagues along with Yu Darvish of Japan and new National Stephen Strasburg.

The Science of Selling Felix, A-Gon Short

In our versions of an offseason blueprint the Red Sox could follow (1, 2, 3) one topic that came up fairly often was how realistic or unrealistic our proposed trade packages were for certain players. Let's recap: Mike Lowell, Casey Kotchman, Clay Buchholz and key minor league pieces (defined as anyone sans Kelly, numbering two) for Felix Hernandez. Money comment: Getting King Felix would be nice, but you are crazy thinking Seattle would have any interest in picking up Lowell or Kotchman. Why would they pick up $16+ in salaries? Lowell is going nowhere unless we pay his salary, which is crazy. - MEe Clay Buchholz, Lars Anderson, Manny Delcarmen, Michael Bowden, two "second-tier" prospects to San Diego for Adrian Gonzalez. Money comment: Delcarmen is a stiff. Bowden is a stiff. Anderson has done NOTHING in the minor leagues. Clay Buccholz has major league stuff but has yet to prove himself for an entire season. For this you'll get one of the best young power hitters in the game? I think not!! - Nick If our proposed deals are not up to snuff, that's not good. Let's try to figure out what a proposed deal could, should be.

Red Sox Offseason BluePrint v.3 : Gonzalez, Holliday, Harden, Sheets

With respect to both Evan and Mike's blueprints and analysis preceding me, I chose to take a slightly different direction with the 2010 Red Sox. I think Theo Epstein and company will be aggressive this off season. No matter what you heard at the end of the season in the "season wrap" press conference from Epstein, I think he's learned from his mistake last hot stove in letting Mark Teixeira slip through their fingertips. While I believe that Theo would rather spend his chips and time trying to pry a young, talented and under team control starter to slot in at the top of the rotation with Lester and Beckett (i.e. Felix Hernandez), I don't believe that will be the route that the Red Sox take given the prohibitive ask that it would take to swing that deal. Trade Clay Buchholz, Lars Anderson, Manny Delcarmen, and Michael Bowden to San Diego for Adrian Gonzalez Instead, despite reports that the San Diego Padres aren't looking to shop their star first baseman Adrian Gonzalez this off season, I think that is exactly where Theo and team will level their gaze, rebuilding their team around a player with nearly all the strengths that they missed out on with Mark Teixeira at a fraction the cost.

Red Sox Offseason BluePrint v.2 : Holliday, Harden, Scutaro

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.