When the Twins finally traded Johan Santana on February 2, 2008, it was the culmination of a lot of things. Minnesota was coming off of a 79-83 season, its worse record since 2000. It's Opening Day payroll had been roughly $71.5 million, by far the highest number in franchise history, and the young-ish core of the team was only going to become more expensive if the organization wanted to keep any of their talent. Terry Ryan had stepped down earlier in the winter, leading to weeks of speculation of how new General Manager Bill Smith would handle the pressure of an off-season that could lose two of its most accomplished, most talented, and most popular players.
Minnesota wasn't going to be able to compete with the five-year, $90 million offer that Torii Hunter accepted from the Angels. But they could control, to a greater extent, the return they would receive for the game's best left-handed starting pitcher: two-time Cy Young award winner, 28-year old Johan Santana. Those moves would also free up money to sign young, cornerstone players like Justin Morneau and Michael Cuddyer to long-term contracts.
Santana would head to New York. The Mets didn't have a particularly strong farm system, but Smith and the Twins took three of their top four prospects, ultimately getting back Carlos Gomez, Phil Humber, Kevin Mulvey, and Deolis Guerra.
Gomez hit .248/.293/.352 in his age-22 and 23 seasons for the Twins, frustrating fans and managers like, before getting traded to Milwaukee for J.J. Hardy. (Remember: a vast majority of Twins Territory was thrilled when the Twins traded Gomez for Hardy; yours truly included.) Hardy, just 27 at the time, was one of the game's premier shortstops whose offense was based around his power. The Twins underestimated his value, a statement which can't be understated any more than that, and in turn dealt him - just 13 months later - to Baltimore for Brett Jacobson and Jim Hoey. Hardy has been worth 13.8 fWAR in the four seasons since; Hoey gave the Twins 24.2 innings of awful relief, while Jacobson didn't last the season in Minnesota's Double-A affiliate. Gomez, meanwhile, turned into a bonafide superstar in 2013 and over the last two seasons has been worth 13.4 fWAR.
Phil Humber was in Minnesota for two years, and gave the Twins 13 relief appearances and 20.2 innings of 6.10 ERA baseball. The upside here was that the Twins were able to use his roster space the following season for somebody that wasn't Humber.
Kevin Mulvey gave the Twins two relief appearances and was dealt on September 1, 2009 to Arizona for Jon Rauch. Rauch was outstanding down the stretch in 2009 out of the bullpen, helping the Twins get to Game 163 in which he pitched a perfect two thirds of an inning. He saved 21 games for the Twins in 2010 while Joe Nathan was recovering from Tommy John surgery, but returned to regular relief duty when the team acquired middling
reliever closer Matt Capps for Wilson Ramos. Rauch became a free agent after that season. The Twins would then choose to spend the money re-signing Matt Capps that they could have instead used to tender J.J. Hardy.
Deolis Guerra, meanwhile, was the youngest player of the foursome to come to Minnesota. He was still 18, and would - through 2014 - pitch in the Twins' minor league system. Since 2012 he's largely been a reliever, posting better strikeout numbers without really turning into an effective pitcher.
On Tuesday, Deolis Guerra signed a minor league contract with the Pittsburgh Pirates. He never made a Major League appearance for the Twins, but was nevertheless the final vestage of what can only be described as the flagship maneuver that helped tank the Major League club. Bad drafts did more damage than this single trade and its subsequent moves ever could, but it certainly - in the end - helped the team truly bottom out.
Guerra will turn 26 in April. He may never salvage any kind of a Major League career, but at this point it hardly seems to matter. The final remnant of what has become a symbol of Bill Smith's decision making has gone, and perhaps we can now literally as well as metaphorically close the door on one of the darker periods in Twins history. No, losing Guerra doesn't mean the Twins will become a better team as a result, but much like letting go of that one ex you just can't stop thinking about - moving on is healthy.
In some sense, it just feels good to say goodbye to it all. Even if this trade hasn't had a tangible affect on the makeup of the Minnesota Twins in a couple years, the slate is now officially clean.