The Best American League Free Agent Signings of All Time

Teams ideally build through the draft and their own farm system, however, free agency is unavoidable. Whether it’s making a huge splash for the top-of-the-rotation starter or plugging a hole on the bench, it’s necessary for teams to utilize the free agent market to fill out their roster. Scott Maxwell brings us the best American League free agent signings of all time.

Free agency began in 1976 and forever changed the landscape of Major League Baseball. With one of the greatest free agent signings of all time finishing up his career with the Boston Red Sox in 2016, it is a good time to take a look at the top free agent deals for every MLB franchise. For the sake of this discussion, this is only for players with prior MLB experience changing uniforms.

This is the first of a two-part series, beginning with the American League and concluding with the senior circuit. There are a remarkable seven one-time Red Sox making the list.

American League

Baltimore Orioles

Roberto Alomar, 1996

The well-traveled Hall of Fame second baseman was signed to a three-year deal in the 1995 offseason. During his stay in Baltimore, he was an All-Star each season, won two Gold Gloves, and the club made the ALCS twice. Despite occasionally expectorating on umpires, his time in Baltimore was hugely successful.

Boston Red Sox

David Ortiz, 2003

As David Ortiz’s career winds to a close with the Boston Red Sox, he will undoubtedly go down as the best free agent signing in club history. Big Papi helped lead the Red Sox to three titles, slugged 445 regular season home runs*, and had an other-worldly 1.372 OPS in his three World Series appearances. The Manny Ramirez signing may have been the most flashy, but there’s no doubt that the Large Father deserves the pole position here.

*and counting

Chicago White Sox

Carlton Fisk, 1981

This one stings. The bumbling imbecile Haywood Sullivan God rest his soul allowed the Red Sox franchise catcher and New England native to leave for Chicago when he famously failed to mail Fisk his contract in time. Fisk went on to play 13 more seasons for the White Sox, hitting 214 home runs and closing out his Hall of Fame career wearing the wrong color Sox. In an effort to woo Fisk to don a Red Sox cap on his Hall of Fame plaque, the Red Sox went against team policy and retired Fisk’s number. Although fences have been mended, it would have been nice to see the one and only Pudge spend his entire career in Boston.

Cleveland Indians

Roberto Alomar, 1999

Making his second appearance on this list, Alomar’s time in Cleveland surpassed his years in Baltimore. Alomar finished in the top four of MVP voting twice for the Indians. Cleveland made the postseason two times during his tenure by the lake, and was a heroic Pedro Martinez relief appearance away from reaching the ALCS. I’m sure he still pops that game in the VCR from time to time as he had a great seat to one of the best performances in playoff history.

Detroit Tigers

Victor Martinez, 2011

The Tigers list of free agents isn’t as robust as some of the others on the list, but they have made the occasional big splash. Martinez came up as a catcher, transitioned to first base, then was ultimately signed by Detroit to serve as their designated hitter. He helped the club reach the postseason twice and came in second for the 2014 MVP. Martinez briefly played for the Red Sox in 2009-10 before leaving as a free agent. Martinez batted .364 in the 2013 ALCS against his former club, only to have Shane Victorino crush his World Series dreams in Game 6.

Houston Astros

Nolan Ryan, 1980

The Ryan Express stopped in Houston for eight seasons. Ryan led the league in strikeouts for four of those. He was a workhorse that could be counted on for 200 innings and 30 starts every year. Though he never won a Cy Young, Ryan led a franchise that had never been to the playoffs before his arrival to the postseason three times. In his age 40 season, he led the league in ERA and strikeouts. However, he only finished with an 8-16 record as he got Pedro-esque run support and that likely kept him from topping the Cy Young voting.

Kansas City Royals

David Cone, 1993

David Cone made a triumphant return to his native Kansas City and the team that drafted him. The franchise is short on big name free agents as a small-market club, but Cone certainly qualifies. He won the 1994 AL Cy Young award and amassed a respectable 27-19 record for a middling Royals team. He was dealt to Toronto before the final year of his deal. Cone played one season for the Red Sox, in 2001.

Los Angeles Angels

Vladimir Guerrero, 2004

One of the last of a parade of All-Stars to leave Montreal, Guerrero helped the Angels reach the postseason in four of his five seasons with the club. Three of those postseasons were ended by the Boston Red Sox, but Guerrero and the Angels finally defeated Boston in 2009. Vlad won the AL MVP in 2004 and finished in the top 10 the following three seasons.

Minnesota Twins

Jack Morris, 1991

Although Morris’s stay in his native Minnesota lasted only one season, he had a tremendous impact. After finishing the season with an 18-12 record, he had a postseason for the ages. Morris went 2-0 with a 1.17 ERA in the 1991 World Series. He won an epic 1-0 decision in Game 7 to help seal MVP honors.

New York Yankees

Reggie Jackson, 1977

The team with the most money to spend is bound to have quite a few players on the list. Jackson’s tumultuous stay was highlighted by three World Series appearances and two titles. Jackson earned the nickname ‘Mr. October’ for his postseason heroics, including hitting three home runs in Game 6 of the 1977 World Series. His assassination attempt on Queen Elizabeth II would later tarnish his legacy.

Oakland Athletics

Dave Stewart, 1986

Stewart was picked up off the scrap heap and, much like Ortiz, turned into a key component for a World Series team. He was released by the Phillies in May of 1986 and signed two weeks later with Oakland. While Roger Clemens kept him from winning a Cy Young, he got the best of the Red Sox in the 1988 and 1990 postseasons. Stewart won 20 or more games four straight seasons and was part of the 1989 world championship team. Stewart is now the GM of the Arizona Diamondbacks and president of the Shelby Miller Fan Club.

Seattle Mariners

Adrian Beltre, 2004

Although Beltre posted some of his more disappointing offensive numbers during his years at Safeco, he still managed to hit between 19 and 26 home runs in his first four seasons with Seattle. Beltre also won two Gold Gloves during his tenure. He played for the Red Sox for one season after leaving Seattle and returned to MVP form while leading the team in tackles.

Tampa Bay Rays

Carlos Pena, 2007

The Rays not only have a much shorter history than most of the clubs on this list, they typically sit out significant free agent signings as a small market club. Pena was a Northeastern University product and former top-10 pick. Pena never fully realized his potential, that is, until he went to Tampa. On the fringe of being out of baseball, Pena miraculously and naturally launched 46 bombs in his inaugural season with Tampa Bay and finished 9th in the MVP voting in consecutive seasons. Pena was also on the 2008 club that captured the franchise’s only AL Pennant, largely due to the duo of David Price and Steve Harvey.

Texas Rangers

Alex Rodriguez, 2001

The Rangers made one of the biggest free agent deals of all-time, signing Alex Rodriguez to a then-record 10-year, $252M deal. Although he was dealt after just three seasons, his production was insane. Rodriguez won the 2003 MVP and finished second and sixth in his other two seasons with Texas. His OPS from 2001-2003 were 1.021, 1.015, and .995. The team finished in last place all three seasons, and after nearly being dealt to the Red Sox, he went to the Yankees in 2004. That trade set in motion the events leading to the Greatest Comeback of All-Time with the Red Sox overcoming an 0-3 deficit in the 2004 ALCS to eventually win their first World Series in 86 years. Thank you, Texas.

Toronto Blue Jays

Roger Clemens, 1997

Clemens was already a 3-time Cy Young winner when he arrived in Toronto for his age 34 season, though his final few seasons with Boston were not his best. Clemens allegedly trained really hard with Brian McNamee and returned to vintage form. Clemens won the AL Cy Young award both seasons, posting ERAs nearly half of what they were in his final seasons in Boston. He also pitched over 230 innings and had over 270 strikeouts both seasons. He was shipped off to New York and his turn to the Dark Side was complete.

*Click here for part 2

SoSH Baseball strives to provide quality, informative, entertaining, and critical baseball content for all fans of the game at any level.

Follow Scott on Twitter @marbleheader75.

About Scott Maxwell 5 Articles
Scott is a teacher, husband and father living in New Hampshire. His hobbies include travel, collecting baseball cards, playing wiffle ball, and digging in to the history of baseball. He has been a moderator and member of for over a decade and has led discussions with John Henry, Ben Cherington and Mike Hazen.

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