Jason Bay was 31 when the Red Sox cut him loose. Victor Martinez was about to turn 32. For that matter, Johnny Damon was essentially the same age, and the Red Sox logic was basically the same on all of them.

Those players were at or near the end of their peak years, and to spend big money on them would be regrettable by the time they crept into their mid-30s.

Well don't look now, Red Sox fans, but Carl Demonte Crawford will be 31 years old on Aug. 5 of this year, and there is simply no way of knowing whether he will have played in a game this season by that time. Prior to last night's Battle of the Soxes between the Boston Red and Chicago White at U.S. Cellular Field, the Red Sox announced that Crawford has a "sprain" of the ulnar collateral ligament in his left elbow, which is a nice way of saying that Crawford has a partial ligament tear.

According to the same release, "a conservative treatment protocol was recommended," and Crawford, based on some estimates, will miss roughly three months. No surgery.

For now.

Before we start discussing whether Crawford has now entered the competition for The Worst Free Agent Signing in History - and he has - let's focus on the truly worrisome part of this news for the Red Sox. These are supposed to be Crawford's peak years. These are the seasons in which the Red Sox should have received the biggest bang for the buck. Following the 2010 season, when the Sox signed Crawford to a whopping seven-year, $142-million contract, the Red Sox told us that their research suggested someone like Crawford would age relatively well, which is why they seemingly broke their own rules and gave Crawford the third-biggest contract in club history behind Manny Ramirez ($160 million) and Adrian Gonzalez ($154 million).

Now, as Crawford approaches his 31st birthday, he doesn't seem to be aging well at all. He had wrist surgery over the winter. Now he has a ligament problem in his elbow. All of this comes after a 2011 season in which Crawford batted .255 with just 18 steals in 24 attempts, all while posting a .694 OPS that ranked 61st among the 74 American League players with at least 500 plate appearances, just ahead of thunder sticks like Cliff Pennington and Robert Andino.

Like your old man might have told you: $20 million a year just doesn't get you what it used to.

What the Red Sox really need to ask themselves is why the Crawford mistake happened and whether it could have been avoided. Was Crawford really "a baseball signing," as owner John Henry has alleged, or was the acquisition more driven by the desire to hike television ratings and fan interest? Before Crawford came along, the Red Sox believed in plate discipline as much as anything else. Then they spent $142 million on a relatively free-swinging slasher who had never so much as hit 20 home runs in a season.

We said it then and we'll say it now: we love when the Red Sox throw their weight around by walking into a room and tossing their overstuffed wallet onto the table. But Crawford was never worth anything close to $20 million a year. That kind of cash is reserved for ace pitchers and skilled power hitters, men like C.C. Sabathia and Roy Halladay, Alex Rodriguez, Albert Pujols and Miguel Cabrera.

The point is that Crawford was a bust before he played a single game in Boston. Now he is merely venturing into the territory of historic bust.

Beyond the current on-field and clubhouse issues with Bobby Valentine and a roster of players that remains largely overpaid and underachieving, the Red Sox' bigger-picture problems in recent years have been obvious. When the Red Sox were at their best in the first five or six years of this ownership group, they had the best of all worlds - the spending power of a big-market team and the player development operation of a small-market club. This past winter, especially, they had neither. A collection of bad signings - Crawford, John Lackey and Daisuke Matsuzaka alone account for $327.5 million - coupled with a developmental drought meant the addition of no significant impact talent on this year's Opening Day roster, leaving general manager Ben Cherington to plug holes with people like Vicente Padilla, Cody Ross, Ryan Sweeney and Kelly Shoppach.

Those kinds of players are absolutely fine if you have a stud coming up through the minor league system. But if you don't - and you're limited to small pickups - there's really no difference between you and the Pittsburgh Pirates.

In the case of Crawford, let's hope the Red Sox learned their lesson. If they (and you) are smart, they'll write off Crawford for this year and start exploring ways to mitigate the damage in future seasons, either by eating money and trading him (highly unlikely) or by lowering expectations. (Translation: build your team as if he weren't here.) What if Crawford is heading toward Tommy John surgery, the way John Lackey was when the Red Sox made that deal? (Lackey's was another curious one given Lackey's age and injury history) Anyone who believes it's not a possibility is living in a land of make-believe.

Hilarious, right? When Bay was 31, the Red Sox pulled out of a four-year deal worth $60 million. With Damon, the Sox would offer no more than four years and $40 million. Now Crawford has five years and more than $101 million remaining on his deal as he approaches his 31st birthday, and we're supposed to think there is some chance this could still be a good deal.

No shot.

What a train wreck.