All great things come in fives. Jacksons. Golden rings. Police Academy movies (I stopped watching them after the fifth). In that spirit, we bring you Poll Position—a new interactive exercise in obsessive Boston fandom (1988-2008). We list. You vote. We all discuss. Euphoric insanity ensues. Let’s roll.

Today, with the trade deadline looming, we take a look at the five best Red Sox deadline moves of the past 20 years. Tomorrow we’ll look at the five worst and on Thursday, we’ll vote on the five strangest deadline moves since 1988. Enjoy!

July 6, 1995: Frank Rodriguez and JJ Johnson to the Twins for Rick Aguilera

Rodriguez was the prototypical Red Sox prospect of the mid-90s. A guy we always heard was going to be a star; who was perpetually one year away from realizing his potential. But like almost all the guys from that era (not named Nomar) he never materialized and the Sox sent him to Minnesota for Aguilera to sure up the pen for the stretch run.

Aguilera picked up two wins and 20 saves (while rocking a 2.67 ERA) as the Sox won the 1995 pennant…and were subsequently swept by Cleveland in the ALDS. Man, the ’90s were awesome.

Rodriguez had a career high 13 wins (and 14 losses) for the Twins in 1996 but was out of baseball five years later, having retired with an impressive 5.53 career ERA.

Note: This wasn’t exactly a deadline move but it was close enough.

Note 2: The Sox made this trade with the Twins while they were playing in Minnesota, which is the same thing that happened with the Nomar trade… teaser.

July 31, 1997: Red Sox trade Heathcliff Slocumb for Derek Lowe and Jason Varitek

This is like one of the old school Red Auerbach deals, except that the guy pulling the strings was more semi-lifeless mannequin than visionary. Still, this deal ranks among the Pedro trade, Manny signing and Nomar’s early extension as the prized pigs of Dan Duquette’s legacy. Not only was this trade partly responsible for two World Series wins, but it also likely saved Slocumb’s life—there had to be at least 10,000 fans teetering on the edge of assassinating him during a game. Just goes to reiterate my theory that you can’t trust anyone named Heathcliff. Unless he goes by Cliff, he’s a loose cannon. That’s not debatable.

Slocumb managed 10 saves down the stretch for the Mariners (who did make the playoffs) but he finished the season with an 0-9 and never earned more than three saves in season before retiring in 2000.

That being said, if Slocumb were active today, at a spry 42-years-old, and the Sox were offered him straight up for Varitek, I think they’d at least have to consider it—as long as he agreed to go by Cliff.

July 30, 1998: Red Sox trade Pete Munro and Jay Yennaco to the Blue Jays for Mike Stanley

This was Stanley’s second go-round in Boston, and even though he was never anything spectacular in a Sox uniform, he was undeniably solid.

With Stanley playing first base and DH, the Sox made the playoffs in both ‘98 and ‘99, and he became one of the faces of those pre-dynasty teams that could never quite get over the hump.

Munro finished his five-year MLB career with a 13-19 record and 4.88 ERA—although he was name to the 2007 Chinese Professional Baseball League All-Star Game!!—and Yennaco won 37 games before retiring in 2003, but all of them were in the minors.

July 29, 2003: Red Sox trade Phil Dumatrait and Tyler Pelland to the Reds for Scott Williamson.

This one has a huge asterisk attached to it. This could have been one of the most important deals in Sox history. Williamson was lights out in the 2003 playoffs and had he come out and shut the door on the Yankees in Game 7 of the ALCS, we’d all look back on this deal differently. But of course, he never got the chance and I don’t want to talk about it anymore. But when you consider, how integral Williamson was in getting the Sox to post-season that season, combined with what we gave up— Pelland is still in the minors, while you can find Dumatrait in Pittsburgh, where he’s currently 3-4 with a 5.26 ERA in 11 starts—it still has to rank up there.

July 31, 2004: Red Sox give up Nomar Garciaparra, Matt Murton and cash in a four-team trade that nets them Orlando Cabrera and Doug Mientkiewicz

This was and probably still is the most shocked I’ve ever been as a Boston sports fan. When the news of Nomar’s trade came over the radio, I was sitting at my buddy Jay’s pool with a bunch of friends, and I’m not sure anyone spoke for next 10 minutes.

Nomar was gone. What could you say?

Ultimately, no one in Boston has any regrets about the deal, but at the time it was crushing.

You ever been in a real crappy relationship that you didn’t realize was so awful until after it ended?

Maybe things started off real well; you thought she was the one. Slowly, things got worse and eventually, bad enough that it was time to cut the chord. Only now you’re living in denial and are busy holding onto the good times and what you thought could be, instead of facing the ugly truth. Eventually things come to an end, and only then, maybe months later, do you have the clarity to look back and think, "Man, what the hell was I doing?"

That’s how I felt about Nomar. I never would have been OK with him leaving Boston, but when I look back at 2004 now, he needed to go. Things were just too sour.

One other note, Murton actually had a decent year with the Cubs in 2006 (.297, 13 HR, 62 RBI), but looks to be on the way out. He was traded to the A’s in the recent Rich Harden deal and is 3 for his first 30 in Oakland.

BONUS DEAL: July 31, 2004: Red Sox trade Henri Stanley to the Dodgers for Dave Roberts

I consider swapping the most pivotal stolen base in major league history for a guy named Henri to be a pretty good deal.

If case you were wondering, Stanley never made it to the majors, although he did it 15 homeruns for the Triple A Las Vegas 51s in 2005, his last year of professional baseball.

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