Looking at 4 of the worst free agent contracts in Chicago Cubs history

(Photo by Brian Kersey/Getty Images)
(Photo by Brian Kersey/Getty Images)
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(Photo by Jim McIsaac/Getty Images)
(Photo by Jim McIsaac/Getty Images) /

With no end to the ongoing MLB lockout in sight, we’re left scrambling for crumbs of news from beat writers, desperately hoping for something big. Earlier this week, we got confirmation of ‘mutual interest’ between the Chicago Cubs and Carlos Correa, perhaps setting the stage for one of the team’s highest profile free agency pursuits in some time – maybe ever.

The team is also reportedly wary of long-term deals and are hesitant to get into that 10-year range in terms of contract length. After all, a 10-year bust is hard to dig out from under. Don’t believe me? Well, look at some of these past nightmares – and none of them were anywhere near a decade long in length (thankfully).

4 of the worst free agent contracts in Chicago Cubs history: Edwin Jackson

Did you know the Cubs paid Edwin Jackson $13 million to not pitch for the during their 2016 World Series run? You do now. One of the biggest swings-and-misses of the Theo Epstein era, the right-hander never came remotely close to being a worthwhile investment during his time in Chicago.

Inked to a four-year, $52 million deal ahead of the 2013 season, Jackson kicked things off by losing a league-high 18 games that year, allowing more than 10 hits per nine. If you think things got better from there, you’re sorely mistaken.

In 2014, Jackson was actually much, much worse than the year prior. His ERA ballooned from 4.98 to 6.33 as he went 6-15. In his defense, his FIP both years was semi-respectable, but no one remembers any of that when you are as ineffective as he was.

He got the chance to compete for a spot in the rotation the following spring, lost that battle to Travis Wood and headed to the bullpen as the long man. He pitched well, but Chicago still designated him for assignment in July, eating his salary not only for that year, but, as I noted, the following season, as well.

All Jackson has going for him is this: he’s the only player in big league history to play for 14 different franchises. As far as Cubs fans are concerned though, he represented a massive whiff from Epstein in the early years of his tenure.

Mandatory Credit: Jonathan Daniel/Getty Images
Mandatory Credit: Jonathan Daniel/Getty Images /

4 of the worst free agent contracts in Chicago Cubs history: Todd Hundley

Maybe because of my age, I remember Todd Hundley being a Cubs catcher but… I didn’t remember how fantastically terrible he was during his time in Chicago.

Son of Cubs legend Randy Hundley, the former second-round pick had cemented himself among the best catchers in the league as a member of the Mets, earning back-to-back All-Star nods in 1996 and 1997. After two years with the Dodgers, Hundley inked a four-year, $23.5 million contract with Chicago ahead of the 2001 season.

While he was never what he was in the Big Apple in Los Angeles, Hundley had still been a solid offensive catcher. He hit 24 home runs in each of his two seasons there, slashing 241/.331/.499 – good for a 112 OPS+. But when he came to the Windy City, the wheels just totally fell off the wagon.

Hundley batted just .199/.285/.398 in 579 plate appearances with the Cubs, who saw enough after just the second year of his deal, trading him back to the Dodgers. The good news? Eric Karros and Mark Grudzielanek, both of whom played critical roles for the ill-fated 2003 team, came back in the deal.

(Photo by Lisa Blumenfeld/Getty Images)
(Photo by Lisa Blumenfeld/Getty Images) /

4 of the worst free agent contracts in Chicago Cubs history: Milton Bradley

Woo, boy. Milton Bradley. What can I say that hasn’t already been repeated ad nauseam over the years? I mean, if nothing else, he certainly lived up to his reputation. The only problem being his reputation was far from sterling even at the time of the signing.

Chicago signed Bradley to a three-year, $30 million contract in January of 2009, looking to add a new look to a lineup that was dominated by right-handed hitters. As far as the numbers go, he was exactly league average for the Cubs – but there was so much unrelated to his on-field performance that played into this falling to pieces quickly, it’s unreal.

He made some really lackadaisical mistakes during his brief stop on the North Side, clashed with manager Lou Piniella and ultimately decided to put the organization on blast in a newspaper interview, commenting, ” you understand why they haven’t won in 100 years here.”

That got him suspended for the rest of the 2009 season and Jim Henry sent him packing in a trade with the Mariners that netted Carlos Silva, who had a solid final year in the bigs with the Cubs in 2010, going 10-6 with a 3.75 FIP and 100 ERA+.

Mandatory Credit: Jonathan Daniel /Allsport
Mandatory Credit: Jonathan Daniel /Allsport /

4 of the worst free agent contracts in Chicago Cubs history: Jeff Blauser

Again, in no particular order, we wrap up this look at four of the worst free agent contracts in Cubs history with Jeff Blauser. At the time of the signing, fans breathed a sigh of relief: a notorious Cubs killer was finally on our side.

Unfortunately, he left his bat at home.

Blauser, who hit a staggering .351/.413/.611 against the Cubs during a decade-long stint with the Braves, came to Chicago on a two-year, $8.4 million pact prior to the 1998 season. During that run, he put up an 79OPS+ and batted a cumulative .226/.343/.342 for the North Siders. That came on the heels of his final year in Atlanta, when he earned the second All-Star appearance of his career – only increasing the disappointment and scrutiny.

Next. A comprehensive list of the greatest Cubs players ever. dark

The veteran infielder hung his spikes up after that underwhelming 1999 campaign due to injuries. A two-year deal for Blauser might not seem like a bust worthy of this list, but watching him decimate Cubs pitching for 10 years only to join the team and fall to pieces was a tough pill to swallow.

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