5) Rick “The Rooster” Burleson  

A fan favorite known for his intensity, laser arm, and dirty porn mustache, Burleson was the shortstop for the storied Red Sox teams of the 70’s.  Making his debut in 1974, he was an immediate hit, finishing 4th in Rookie of the Year voting.  The Rooster was the Red Sox SS for seven seasons, was elected to three straight All-Star games, and currently holds the MLB record for most double-plays turned in one season. 
Note: Rick edges Vern Stephens here for #5; Stephens was outstanding for Boston, but for a rather brief period of time.

4) Rico Petrocelli

Nowadays, when a player suddenly breaks out from relative mediocrity and has a 40 HR season, what does everyone say?  That’s right: the “S” word.  Drives me kind of crazy.  People act like there has never been a fluke power season before 1997, like there is no possible way that a human being can actually work out and get stronger without visiting a Mexican drug-store.  Well, that just isn’t the case.  Rico, my paisan, had the following line in 1968: .234/.292/.374 with 12 HRs.  In the very next season, Rico belted .297/.403/.589 with 40 HRs.  Now, they did lower the mound in 1969, which certainly had some effect…but lowering a pitcher’s mound will not turn Walt Weiss into A-Rod, which is basically what happened with Rico.  He just got better, plain and simple.
If Rico played today and had that type of improvement at the plate, you would see Bud Selig, Bob Ryan, and five grandstanding congressmen climb up his ass.
 
3) Johnny Pesky

There are several things we can blame on Hitler.  Here is one more to add to the list:  Johnny Pesky’s absence from Cooperstown.  I’ll break it down like this:
Age 22: .331/.375/.416, 205 hits (3rd in MVP voting)
Age 23: WWII, did not play
Age 24: WWII, did not play
Age 25: WWII, did not play
Age 26: .335/.401/.427, 208 hits (4th in MVP voting)
Age 27: .324/.393/.392, 207 hits

Now, what type of performance would Johnny likely have had if he played from age 23-25?  We can only guess…but an educated guess would put him at #1 of this list, and in the Hall.
Johnny wasn’t a defensive wiz, but he was solid, much better than his reputation after 1946.  I’ll forgo the obligatory Johnny ball-washing, only to say that he is quite possibly my favorite player of all-time.
     
2) Joe Cronin

The list isn’t based on personality or likeability, otherwise my homeboy here would have to get behind Johnny.  Cronin is what he is: a Hall of Fame shortstop, excellent both defensively and offensively.  Making 5 All-Star games with Boston and posting a career OPS+ of 119, Joe was basically your segregation version of Derek Jeter, glove notwithstanding.
Cronin would later become GM of the Red Sox, and basically flush the entire franchise down the toilet via foolhardy acquisitions and stubborn racism.  But, that is a list for another day.
I had a difficult time choosing between Cronin and the next guy for #1…
  
1) Nomar Garciaparra

I’ll keep it brief; you know just as much about him as I do at this point.
Nomar edges Cronin with his bat.  He was a good defender early in his career, until nagging injuries began to limit his range, which in turn began to lead to haphazard throwing errors.
Next to Wade Boggs, the best line-drive hitter I have ever watched (save the e-mails, I’m in my 20’s and I watch Red Sox games).  Still has an outside shot at the Hall of Fame, if he can manage to keep the trainer from running out onto the field in LA.

In 2007, the Sox will deploy newly-acquired Julio Lugo at shortstop.  Lugo comes with rave “intangibles” reviews from his prior teammates and coaches: great clubhouse guy, leader, fiery.  Defensively and offensively, Lugo is solid.  Doesn’t have great plate discipline, but can run the bases.
The Sox spent a large chunk of change Julio, basically due to the lack of viable options at the position. 

However, it appears that the era of superstar shortstops is dying down a bit.  A-Rod has moved.  Jeter is a tremendous hitter, but is a hack on the field.  Ditto Tejada.  These guys aren’t going to sprout out of the ground like they did in the 90’s, and locking up Julio Lugo could prove to be a very prudent move.