No short answer

It's one of those days in recent Red Sox history. Any 20-something Red Sox fan can likely remember where he or she was standing when it happened. I was at Tanglewood in Western Massachusetts, and when I was first told the news I didn't believe it.

Nomar was traded.

It's a signficant moment in Red Sox history, seeing as how it was the springboard to ending 86 years of misery, etc. etc. But in looking back on things it's interesting for an entirely different reason.

It's the last time Theo got the shortstop thing right.

I'm certainly not debating the Nomar trade. In fact, it was a stroke of genius. Nomar wasn't a happy camper in Boston anymore, and that became painfully obvious to anyone in the Sox clubhouse that summer. His negativity was clearly affecting a team struggling to find an identity, and his replacement - Orlando Cabrera - proved the perfect fit for the free-wheeling, Cowboy Up, self-proclaimed Idiot Red Sox. The fact that his glove was golden didn't hurt, either.

But in the afterglow of the World Series win, Theo let Cabrera walk away, signing the introverted Edgar Renteria for way too long and way too much, thus starting a now three-year-long revolving door at the shortstop position, a spot currently manned by the maligned Julio Lugo, he of the undersized batting average and oversized error count.

But we can't talk about Lugo until we recap how we got here. Renteria turned out to be a complete failure, struggling to handle American League pitchers, American League grounders and a ravenous Boston press that didn't ease his transition. He may be the only Red Sox free agent whose English got worse as his stay with the team got longer. (What? Errors? I'm sorry, I don't understand.)

The next twist is the most maddening to diehard Sox fans in that Epstein found the solution - and let it slip away again. Renteria was replaced by Alex Gonzalez, and Sox fans were treated to the best defensive season ever turned in by a Red Sox shortstop (that Gonzo didn't win a Gold Glove should be under federal investigation ... paging Arlen Spector). Gonzalez came with an all-defense and no-offense reputation but managed to hit almost .260 for the year while making all the routine plays and nightly superhuman ones. It should also be noted that he cost only a couple million dollars.

Enter Mr. Lugo. For whatever reason, Epstein had long been infatuated with the skinny shortstop, and media reports had him linked to Boston in a handful of trade rumors over the years. So when he became available as a free agent everyone expected Epstein to go after him hard. That he did, throwing $36 million at Lugo.

Given the way things have gone, one can only assume Lugo had a hard time catching it all.

Lugo has fulfilled almost none of the promise the Boston brass tried to sell Red Sox Nation. He stole a bunch of bases last year and actually played some strong defense, but he struggled to hit .200 for the better part of the year. And this season he's hitting better, but his stolen bases are down and his defense has been awful. He even became almost an afterthought when youngster Jed Lowrie got a cup-of-coffee earlier this spring. Either way, I don't think anyone envisioned Lugo filling the nine hole on a nightly basis when he signed his name on the dotted line.

It's an unusual chink in Epstein's armor, the only Kryptonite to our boy wonder GM. He plucked David Ortiz from the Twins, filled third base with Bill Mueller and Mike Lowell (two of the classiest dudes ever to wear a Sox uniform), and stocked the pitching staff with young arms. He also traded for Curt Schilling and built two World Series winners. But for whatever reason Epstein keeps coming up with an E-6.

With the trading deadline fast approaching, rumors are beginning to swirl again that the Sox are in the market for an upgrade at shortstop. It's hard to imagine a scenario in which a change takes place - Lugo will be extremely difficult to move, and it's unlikely the Sox make a trade and shelf Lugo on the bench. Nobody wants a $36 million back-up infielder.

But perhaps a trade is the best possible solution. Epstein may not have a dazzling track record in hunting shortstops via free agency, but the last time he traded one - and traded for one - the season ended with Johnny Pesky weeping in the clubhouse.

And Jimmy Fallon jumping for joy on St. Louis' field. I'm going to go take a bath in paint thinner now.

Anyway, whether the Sox upgrade their situation at shortstop before the end of the season is anyone's guess. To be perfectly honest, I think this team is good enough to win a title even with Lugo on the roster. But if I were Theo I'd cut my losses in the off-season and try a new approach for next spring.

Leave the free agent list in a desk drawer somewhere and make a phone call to Pawtucket. It'll safe Epstein the trouble of trying again, and I think Red Sox Nation would be quite comfortable giving the keys to the shortstop position to Lowrie.

If losing Cabrera and Gonzalez has taught the Sox anything it should be that sometimes the grass is greener on the side you're already on.