By Marc Thaler
Sports Editor

I’ll take What happened while I was away on vacation? for $1,000, Alex ...

As I felt the soft sands of St. Lucia beneath my feet, the Red Sox allowed one of baseball’s best leadoff hitters – and a solid center fielder – to walk.

Exactly how Boston’s front office allowed this to take place still doesn’t add up. Then again, it does. Count to 12, then say “million dollars.” That was the difference between a pair of four-year contracts offered to Johnny Damon by Boston and the Bronx Bombers.

Once again, Fenway’s faithful, who religiously pay excruciatingly expensive prices to watch their team, were left wondering why an organization with one of baseball’s biggest bank accounts didn’t come closer to Damon’s asking price. We know the Sox could’ve, they just refused.

The power players in Boston’s front office would have you believe Damon’s best days are behind him. Offering the Hub’s handsome rock star anything more than a four-year deal at $10 million a season would be an impractical investment.

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My problem had little to do with the offer made. Under the St. Lucian sun, I really sizzled thinking about the negotiating tactics taken by the management team; a team, remember, whose leader – principle owner John Henry – continues to appear more fearful than fearless.

With Damon serving as the latest example, the Sox continued their tired trend of waiting until it’s too late to re-sign freeagent personnel. I’m talking about impact players, difference makers.

Forget on-field stars for a moment. Former general manager Theo Epstein quickly comes to mind as an individual who should’ve been re-signed long before reaching the conclusion of his contract.

Basically, when the Sox have all the time in the world to bargain with their boys, they opt to wait. And when you wait, egos often dictate it’s too late.

The business of not negotiating during the season is ludicrous, especially when dealing with the staples of your squad.

By my count, only once did this tactic work in the organization’s favor.

Prior to the 2005 season, management played hardball with Jason Varitek. Among the game’s best catchers, Varitek signed around the holidays – a four-year, $40 million deal. The Sox believed there wasn’t a large market for catchers, stuck to their guns and signed the current captain on their terms.

But every situation and player is different. I believe the brain trust had another brain cramp and failed to realize as much.

Very few players provide the offensive and defensive production Damon consistently brings to a lineup. At the plate, he’s a tremendous run scorer, an on-base machine. Though base stealing isn’t part of Boston’s philosophy, he’s capable of swiping a bag when necessary.

Defensively, Damon also delivered. His weak arm was an overrated argument in favor of allowing him to leave Boston. I’d invite anyone to name five games the Sox lost during Damon’s Beantown days due to a terrible toss from center field.

The fact is, the Red Sox slipped up again. Management was either arrogant in thinking Damon would never truly leave town or it was ill prepared to negotiate. Take your pick.

Either way, another major mess was the result.

Signing stud pitcher Josh Beckett served as a Band-Aid for the team’s true problem: The organization’s front office has too many cooks in the kitchen.

Thus, nobody can take charge and provide true direction.

How else can you explain why the Sox couldn’t close the gap on a $12 million difference, but were willing to take Mike Lowell – and his $18 million anchor of a contract – to snatch Beckett from the Marlins?

How else can you explain trading Edgar Renteria one year into a four-year, $40 million pact, while eating $11 million to ship him to Atlanta?

Even with a cloud of chaos hovering over the Red Sox, Boston will always be an attractive place to play. For years to come the Sox will still have their share of key free-agent signings and blockbuster trades.

That’s never a concern.

The Red Sox might be able to teach the class how to bring big guns to town. But they have a lot to learn in the course “Keeping the key contributors already in your clubhouse.”

I’ll always remember the day Damon departed. While dousing one of many Caribbean meals in a sauce called Jerk, I learned of Boston’s inability to retain the services of its biggest Idiot.