List: Most significant Red Sox trade deadline deals since 2000

July 30, 2014 - 7:02 am

The trade deadline is just one day away. And after another loss Tuesday night, it appears likely the last-place Red Sox will not only be active sellers from now until 4 p.m. Thursday, but some big names could be on the move. The fire sale began this past weekend when the Sox sent Jake Peavy to the Giants for a pair of pitching prospects. Since then, multiple players within the organization have been involved in trade rumors, including Jon Lester, Andrew Miller, Koji Uehara and a few others. This certainly isn't the first time the Red Sox have been active participants in the deadline madness since the turn of the century, for better or worse. The Sox have shown they're not afraid to make a splash in July to bolster their roster for a playoff push. However, even some of their least notable deals at the time have proven to be the different between a World Series championship and an early exit. Here are the Red Sox' top 10 most significant trade deadline moves since 2000. 10. July 30, 2002: Red Sox receive outfielder Cliff Floyd, send right-handers Seung Song and Sun-Woo Kim to the Expos The Red Sox were in the midst of a pennant race by July 2002 and bolstered their lineup by trading for Floyd. The slugger was a key bat for the Sox, hitting .316/.374/.561 in 47 games and 171 at-bats. But it wasn't enough to propel the 93-win Red Sox into the postseason, and Floyd left as a free agent after the season. 9. July 31, 2011: Red Sox receive left-hander Erik Bedard and right-hander Josh Fields, send catcher Tim Federowicz and right-handers Juan Rodriguez and Stephen Fife to the Dodgers Bedard, who was acquired from the Mariners in a three-team deal, was supposed to be a nice arm to join the rotation and help the Sox in what looked like an inevitable postseason run. But like the Red Sox of September 2011, Bedard failed to replicate past success. The lefty pitched a combined 38 innings over eight starts and finished with a 4.03 ERA before leaving after the season. 8. July 31, 2010: Red Sox receive catcher Jarrod Saltalamacchia, send first baseman Chris McGuiness, right-hander Roman Mendez and catcher Michael Thomas to the Rangers With Jason Varitek's career nearing an end and Victor Martinez's contract expiring, the Sox acquired Saltalamacchia to be their catcher for the upcoming future. The deal proved valuable for the Red Sox as Saltamacchia gave them three strong seasons with over 100 games played and was key in their 2013 World Series run. He hit .273/.338/.466 in 121 games for the Sox last season before signing with the Marlins in the offseason. 7. July 31, 2007: Red Sox receive right-hander Eric Gagne, send left-hander Kason Gabbard and outfielders David Murphy and Engel Beltre to the Rangers The Red Sox strengthened their bullpen at the deadline by adding Gagne, a longtime closer who waived his no-trade clause and agreed to be the setup man for Jonathan Papelbon. Gagne started the year in Texas looking like his old self following two elbow operations and back surgery, but he imploded upon joining the Red Sox. He allowed 14 runs in 18 2/3 innings and blew all three of his save opportunities, proving to be more of a liability out of the bullpen. The trade, however, proved to be of little consequence because the Red Sox won the World Series that year despite Gagne's 6.23 ERA in the postseason, and only one player, Murphy, proved to be of any value. Murphy was a key part of the Rangers' two World Series appearances in his six-plus years with the club. He's hitting .272/.335/.432 in his big league career and is in his first season with the Indians. 6. July 30, 2013: Red Sox acquire right-handers Jake Peavy and Brayan Villarreal, send shortstop Jose Iglesias to the Tigers and right-handers J.B. Wendelken and Francelis Montas to the White Sox The Red Sox needed one more reliable starter before they were prepared to make a run at the 2013 World Series, and Peavy was the guy. The Sox acquired Peavy in a three-team deal with the White Sox and Tigers, with their most significant loss being Iglesias, who made a living with his glove but struggled as a hitter. Peavy proved to be a key part of the rotation for the 2013 stretch run -- he posted a 4.04 ERA in 10 regular-season games with the Sox -- and started the ALDS clincher against the Rays. Peavy (1-10, 4.71 ERA) saw his career in Boston come to an abrupt end this past weekend when he was dealt to the Giants. 5. July 31, 2003: Red Sox receive right-handers Jeff Suppan, Brandon Lyon and Anastacio Martinez, send second baseman Freddy Sanchez and left-hander Mike Gonzalez to the Pirates Of the trades on this list, this maight go down as the worst for the Red Sox. The Sox were about to embark on an exciting postseason run, but they needed some extra arms to bolster their pitching depth. They did so by shipping off a pair of promising young talents in Sanchez and Gonzalez in exchange for three pitchers who lasted no more than a few months with the Red Sox. Suppan had a 5.57 ERA in 11 games for the Sox in 2003, Lyon's Red Sox career lasted 59 innings as he blew three of 12 save opportunities, and Martinez pitched just 10 2/3 innings for the Sox in 2004. Meanwhile, Sanchez gave the Pirates five good years and helped the Giants to a championship in 2010. He hit .297/.335/.413 for his major career. Gonzalez had four strong seasons out of the pen before battling inconsistencies to hold a 3.14 career ERA. 4. July 31, 2009: Red Sox receive catcher Victor Martinez, send right-hander Justin Masterson, left-hander Nick Hagadone and catcher Bryan Price to the Indians Not every trade on this list was a clear-cut win or loss for the Red Sox, and their activity at the 2009 deadline was a prime example of that. Varitek and David Ortiz seemingly were on the decline in 2009 and the end of their careers appeared to be in sight. The Sox countered those concerns by acquiring Martinez in exchange for three prospects. Martinez was solid in his 183 regular-season games with the Red Sox. He was a consistent .300 hitter and was valuable at both catcher and first base. But the Sox also gave up some value in the deal, particularly by trading Masterson. The righty has developed into an ace for the Indians since 2011 despite some recent struggles. Masterson made his biggest impact in 2013, pitching 193 innings over 29 starts and posting a 3.45 ERA and 1.20 WHIP to lead the Indians to a wild card berth. 3. July 31, 2004: Red Sox receive outfielder Dave Roberts, send outfielder Henri Stanley to the Dodgers At the time, this deal was simply a footnote in many baseball reporters' notebooks, especially after the splash the Red Sox made that same day by trading iconic shortstop Nomar Garciaparra. But one legendary moment was all it took for Roberts to forever have a place in Red Sox fans' hearts. Roberts had just 86 at-bats in 45 regular-season games for the Red Sox, but his stolen base in the ninth inning of Game 4 of the ALCS is considered by many to be the turning point in the Red Sox' comeback against the Yankees after trailing 3-0 in the series. Roberts left after the 2004 season. 2. July 31, 2008: Red Sox receive outfielder Jason Bay from Pirates, send outfielder Manny Ramirez to the Dodgers and right-hander Craig Hansen and outfielder Brandon Moss to the Pirates Ramirez will also be remembered for his contributions to the 2004 and 2007 championship teams, along with many other big moments throughout his years with the Red Sox. But by 2008, his antics were getting tiresome. Ramirez got into an altercation with teammate Kevin Youkilis in the dugout during a game, and he infamously shoved traveling secretary Jack McCormick over a ticket dispute. That doesn't even include the countless hamstring injuries he manufactured for a day off. The Sox finally decided they had enough. Theo Epstein executed a three-team deal that sent Ramirez to the Dodgers and Hansen and Moss to the Pirates for Bay. Bay proved to be a worthy replacement for Ramirez, hitting .293/.370/.527 in 49 regular-season games and leading the Red Sox to Game 7 of the 2008 ALCS. Bay left via free agency after the 2009 season. 1. July 31, 2004: Red Sox receive shortstop Orlando Cabrera from Expos, first baseman Doug Mientkiewicz from Twins, send shortstop Nomar Garciaparra and outfielder Matt Murton to Cubs Not only was this the most significant trade deadline deal the Red Sox have made since the turn of the century, but one could argue it was the organization's most notable transaction since Harry Frazee sold Babe Ruth to the Yankees. There lies the significance of the deal. While selling Ruth effectively began the Sox' 86-year World Series drought, many point to the Garciaparra trade as the deal that effectively ended it. There was a time when Garciaparra was an icon in Boston. He won a pair of batting titles and led the Sox to multiple postseason appearances. But with Garciaparra battling an Achilles injury, his contract expiring and the Red Sox middling, Epstein boldly shipped the All-Star to the Cubs in a four-team deal that brought the Sox a pair of defensive aces in Cabrera and Mientkiewicz. The trade sparked the Red Sox through August and September and all the way through October to help them win their first title since 1918. Cabrera and Mientkiewicz both left the team after the season, but their place in Red Sox history is permanent. Garciaparra left the Cubs after the 2005 season. He played three seasons with the Dodgers and one with the Athletics before retiring in 2009. Garciaparra still was productive when he played, but he spent much of his final years battling injuries.