5 Best Free Agent Signing in MLB History

If there’s one sport in which you want to be a free agent, it’s baseball. Typically, teams will grant massive contracts, all of the money is guaranteed, and you tend to find a spot to call home for several years. However, not all players live up to these massive contracts, especially when they get to be eight years in length or longer. Then, there are those free agents that play well above their expectations.

Today, we look at some of the players that ended up being huge bargains for franchises, with some even leading them to championships. Here are our picks for the five best free agent signings in MLB history. Before we start the list, some of the honorable mentions include Manny Ramirez (Boston Red Sox), Roger Clemens (Toronto Blue Jays), Vladimir Guerrero (Anaheim Angels), and Adrian Beltre (Texas Rangers).

5. Reggie Jackson (New York Yankees)

The man that would eventually become known as “Mr. October” was an MVP with the Athletics organization, sticking with the team during their move from Kansas City to Oakland in the late 1960s. After a falling out with the team, though, Jackson departed prior to the 1976 season as he was traded to the Baltimore Orioles where he played for one season.

Heading into the 1977 season, Jackson found a new home in the form of the New York Yankees, with owner George Steinbrenner handing him $2.9 million over five years. That sounds like nothing now, but at the time it was a huge deal, and Jackson delivered. During his five seasons with the Yankees, Jackson had a batting average of .281 with 144 home runs, including many clutch postseason dingers that helped the Yankees win two World Series titles.

4. Larry Walker (Colorado Rockies)

Larry Walker was one of the many eventual greats that started with the Montreal Expos but was allowed to leave after the 1994 strike season. Walker was a one-time All-Star in Montreal, with a lot of teams vying for his services.

The Colorado Rockies took, what was at the time, a huge chance by giving Walker $22.5 million over four seasons. He certainly didn’t disappoint as he hit 126 home runs during his original contract despite missing half of one season. Walker stuck around for a total of 10 years in Colorado, hitting 258 home runs and winning an MVP Award.

3. Randy Johnson (Arizona Diamondbacks)

Though most associate Randy Johnson with the Seattle Mariners early in his career, The Big Unit actually came up with the Montreal Expos before being traded to Seattle during the 1989 Major League season. Johnson was a dominant force with the Mariners, winning 130 games in his 10 seasons and racking up over 2,100 strikeouts.

After the Mariners traded him to Houston to end the 1998 season, Johnson became a free agent and signed with the Arizona Diamondbacks who shelled out a massive $52.4 million contract for four years (and a fifth-year option). Arizona broke the bank with their deal, but it ended up paying off as Johnson won 81 games during that four-year stretch and the 2001 World Series MVP.

2. Barry Bonds (San Francisco Giants)

A star from the get-go with the Pittsburgh Pirates, Barry Bonds spent seven seasons with the team and won the 1990 MVP Award. After a second MVP title in 1992, the Pirates were simply too cheap to sign him to a long-term contract and he became a free agent.

Prior to the 1993 season, the San Francisco Giants signed Bonds to a six-year contract worth $43.7 million. At the time, that was an insane amount, but somehow, Bonds still exceeded the expectations on the contract. Bonds stuck around the Giants beyond his original contract and finished with a .312 batting average and 586 home runs as a member of the Giants in 15 seasons.

1. Greg Maddux (Atlanta Braves)

Greg Maddux originally came up as part of the Chicago Cubs organization after being a second-round draft selection and made his Major League debut in 1986 at just 20 years old. Maddux went on to become a two-time All-Star in Chicago and even won the Cy Young Award, but the team inexplicably let him walk.

Maddux then signed with the Atlanta Braves for five years and $28 million, which was not even close to the highest offer that he received as the Yankees offered $34 million. Maddux was a perfect fit in Atlanta where he went 194-88 with a 2.63 earned run average during his 11 seasons with the Braves en route to a Hall of Fame career. While $28 million was a lot at the time, it was certainly worth it, especially by today’s standards.

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