Chicago Cubs: Who were the best free agent bargains in franchise history?

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Jul 8, 2015; Chicago, IL, USA; St. Louis Cardinals outfielder Jason Heyward against the Chicago Cubs at Wrigley Field. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports /

The Chicago Cubs’ Theo Epstein and crew have a talent for signing under-valued free agents. But do the recent signings rank with the Cubs all-time best free agent bargains?

This off-season has been marked by some big-name players coming to the Cubs to collect some big paychecks. Most notably, Jason Heyward and Ben Zobrist will be hitting the field for the Cubs this season–and hopefully several more.

In order to attain their services, the Cubs had to promise top-dollar contracts.

Just a couple of years ago, the Cubs were reluctant to offer big money contracts. Instead, they signed “rebound” players–players who were coming off down seasons or injuries who would demand less money but could potentially be impact players.

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The strategy worked well–not necessarily in terms of wins and losses, but in terms of the Cubs being able to add value to the team through player trades. Jake Arrieta and Addison Russell are both products of the Cubs sign, produce, and trade strategy.

If the Cubs are going to add any more players to the roster for 2016, after having already signed Heyward, Zobrist and John Lackey, they will likely need to hit the bargain bin again.

The Cubs have gotten excellent value from some low-level signings. Let’s see if you remember some of these good players who came with low costs. On the following slides are the Cubs best “bargain” signings.

There a few ground rules for this list: first, that the player came to the Cubs at well below market value. Second, international, amateur free agents don’t count (that’s too similar to the draft). Thirdly, we’re only counting signings of the modern free agent period (post-1976).

Next: A boost from the G-Man

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In 1998, the Chicago Cubs were enjoying a breakout seasons from Sammy Sosa and Kerry Wood. They were in the playoff hunt, but could not settle a couple of their positions. Third base had been a revolving door for much of the season. Kevin Orie, Jose Hernandez, and Tyler Houston all spent time at the hot corner, each not quite able to lock the position down.

When the St. Louis Cardinals released aging slugger Gary Gaetti, the Cubs front office saw little to lose in offering the former All-Star a contract. He signed with the Cubs for $170,000.

What did the Cubs get? First, they got a veteran presence for their run towards the playoffs. Second, they got an experienced third baseman–they’re best options up to that point had been utility players.

Third, they got a guy who slashed his way to a .991 OPS and gave them stability at the hot corner. Gaetti was a huge part of a Cubs team that ended up winning the National League Wild Card (before falling to the Atlanta Braves in the Divisional Series).

Next: Another midseason steal

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At the start of 2008, Jim Edmonds looked washed up. Then 38-years old, Edmonds seemed past his glory days of smashing home runs and flying across center field for the Angels and Cardinals. By the end of April, the San Diego Padres had seen enough and cut the aging slugger loose.

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At the same time, the Cubs were realizing that unless they found a center fielder, they’re playoff hopes would be washed up. So with very little to lose, they dangled a contract in front of Edmonds (who had been a Cubs’ tormentor for years as a member of the Cardinals).

Edmonds was excited about joining a contending team and signed with the Cubs for a big discount.

For a time, the “Jimmy Baseball” of old returned, as Edmonds slashed his way to a .939 OPS will hitting 19 home runs in just 298 plate appearances. He didn’t have the same range in center as he once did. But he provided a steady presence in the Cubs outfield and was a huge contributor to the Cubs’ playoff team.

Next: A million dollar utility guy?

When the Cubs signed former Texas Ranger Mark DeRosa for $2.7 million before the 2007 season, some thought they were overpaying for a utility guy. But the Cubs saw value in DeRosa, especially as a middle infielder. They got a bit more than were expecting.

DeRosa had shown some moderate power in his Texas days. But he found his power stroke in Chicago, clubbing 21 home runs in 2008.

But DeRosa’s versatility proved key for the Cubs teams of 2007-2008. DeRosa came to play second but ended up playing every position but pitcher, catcher and center field for the Cubs. That the Cubs could count on DeRosa’s consistent bat from just about any position made him a great value for the money he received.

Next: Reclamation project goes right

Ryan Dempster‘s once-promising career was in danger of being cut short in 2003 year. In August of that year, he underwent Tommy John surgery and was later released by the Cincinnati Reds.

In January of 2004, the Cubs took a chance on Dempster and offered him a $300,000 contract, knowing that they may not get any innings out of him that season.

Dempster accepted the contract and returned early from surgery. He pitched well from the Cubs pen that season–well enough, in fact, that the Cubs made them their closer in 2005.

Dempster saved 75 games for the Cubs over the course of three seasons then switched to the starting rotation. As a starter, Dempster won 53 games over three and half seasons and was an All-Star and staff ace before he was traded to the Rangers in 2012–a deal that landed the Cubs Kyle Hendricks.

Next: The Hawks blank check

Hall of Fame player Andre Dawson responds to being introduced during the class of 2014 national baseball Hall of Fame induction ceremony at National Baseball Hall of Fame. Credit: Gregory J. Fisher-USA TODAY Sports /

The free agency world was a bit different in 1986 and ’87. Really, free agency was a little more than a decade old, and owners hadn’t quite yet caught on to the idea of an open market for players.

Players were still considered the property of their teams. So when Andre Dawson decided that Montreal’s Olympic Stadium was killing his body and that he no longer wanted to play for the Expos, nobody else was jumping up to give him a contract — despite that he was a six-time Gold Glover, and All Star, and a possible Hall of Famer. In those days, players didn’t dictate where they played.

So Dawson and his agent did something desperate. They called Dallas Green, then General Manager of the Chicago Cubs, and said that they had already signed a contract with the Cubs… and were willing to accept whatever dollar amount the Cubs wanted to write in.

Next: Cubs Convention filled with hype

The Cubs wrote in $500,000, a figure well below Dawson’s value. They offered bonuses if Dawson played in the All-Star game or won the MVP award in 1987. That season, the Hawk slammed 49 home runs and drove in 137 en route to winning the MVP award–all while playing for a pretty bad team.

Dawson played in four more All Star games as a Cub and twice more drove in over 100 runs. He requested that his Hall of Fame plaque picture him in a Cubs hat, but that request was denied. He was enshrined as an Expo–the team he fled for the Cubs back in 1987.

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The Chicago Cubs’ Theo Epstein and crew have a talent for signing under-valued free agents. But do the recent signings rank with the Cubs all-time best free agent bargains?

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