2002: Helton for Manny Ramirez trade rumors
Speaking of the Red Sox slugger, Ramirez was the bargaining chip in 2002 for Red Sox GM Theo Epstein to sway the Rockies to bring Helton to Beantown. But the Sox also wanted Larry Walker for the Ramirez along with some minor-league prospects. While Manny is one of the greatest players of all time, PEDs or not, Epstein tried to get rid of him on multiple occasions.
There are a multitude of reasons Epstein might have done this, but let’s chalk it up to “Manny being Manny.” Needless to say, this Rockies trade didn’t happen probably because two future Hall of Famers for one and a couple of prospects didn’t line up. Plus that eight-year, $160 million contract Ramirez signed in 2001 probably didn’t help matters. But this wouldn’t be the last of the trade talks sending Helton to the Red Sox.
2007: Helton for Mike Lowell and Julian Tavarez
Then Helton nearly got traded to the Red Sox in 2007. After the 2006 season, it would be unfair to say Helton had fallen off. He hit .320 in 2005 and .302 in 2006. But in both of those years combined, he hit 35 homers. Before that, he had never hit lower than 25. That was in 1998 which was his full rookie season.
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In May of 2006, he had an intestinal infection that he never fully recovered from that year. He was still a great defender but not on the level of the Gold Gloves he was winning earlier in the decade. Derrek Lee and Pujols had a lot to do with that. Helton was still a great asset who could be a huge upgrade for the Red Sox at first base to get their first championship since 2004.
Kevin Youkilis was Boston’s primary starter at first. Youk’s best attribute was his OBP close to .400 every year. Certainly by that point though, he had pedestrian home run numbers, subpar defense, and he didn’t hit for any extraordinary average. By 2007, he had never made an All-Star appearance. Youk is a no-brainer Boston Red Sox Hall of Famer, but Helton would have been an even bigger no-brainer upgrade at first for the BoSox. Helton had a career .430 OBP at the time.