15 worst Chicago Cubs free agent signings in franchise history

The seven-year, $177 million free agent contract given to Dansby Swanson marked a return to big spending for the Chicago Cubs this winter. After unsuccessfully betting on the core of the World Series-winning 2016 team year-in and year-out, the front office finally faced the music and dismantled the group ahead of the 2021 trade deadline.

That sell-off, the financial impact of the COVID-19 pandemic and last winter's lockout kept ownership holding onto its wallet and, now, Chicago is back to flexing its large market muscle in free agency, doling out more than $300 this offseason. But the team's record in free agency is checkered, at best, with some notable swings and misses over the years.

15 Worst Signings in Chicago Cubs History

15. LaTroy Hawkins - 3 Years, $11.2 Million (2004)

If you took a passing glance at LaTroy Hawkins' numbers during his time with the Cubs, you'd easily dismiss his inclusion on such a list. But a closer look tells a different story - one I'm sure Hawkins himself may disagree with.

The right-hander signed with Chicago in Dec. 2003 and he played a key role in the Cubs bullpen the following year. The setup man-turned-closer made a whopping 77 appearances, spanning 82 innings, working to a 3.54 FIP, 4.93 K/BB ratio and 1.049 WHIP. So what exactly is the problem here?

Hawkins blew nine saves as the team's closer, including a key game against the Mets in September that seemed to totally take the wind out of the team's sails. The Cubs dropped six of their last 8 games, falling out of the postseason picture. Coming on the heels of the 2003 run, the late season collapse drew the ire of Cubs fans more than it may have otherwise done and Hawkins was a favorite scapegoat in all of it.

He had a complicated relationship with fans and the media - and the fact he blew more saves from 2004-05 than any other pitcher in baseball certainly didn't win him much support. His numbers ballooned early in 2005 (5.49 FIP, 1.86 K/BB in 21 appearances) and the Cubs shipped him off to San Francisco in a trade, less than halfway through his three-year contract.

14. Tyler Chatwood - 3 Years, $38 Million (2018)

In recent memory, there are few moves that prompted as much confusion from the fanbase as the Tyler Chatwood signing. In Dec. 2017, Theo Epstein and Jed Hoyer handed the right-hander a three-year, $38 million pact, despite the fact he was coming off a a 4.94 FIP and 1.442 WHIP, major league-leading 15-loss 2017 season.

Convinced they could turn his top-tier spin rates into effectiveness, the Cubs hoped he could add some overpowering stuff to the rotation mix. Instead, the right-hander led all of baseball with 95 walks in 2018, despite losing his role as a starter and being benched for essentially the last month of the season.

Chicago attempted to recoup some hope of respectability out of the Chatwood signing in 2019, when they transitioned him to a bullpen role - and he was definitely more effective there. He managed a 3.67 ERA as a reliever, also stepping in to make five spot starts on the year. He closed out his Cubs career during the fanless, shortened 2020 season - and it wasn't great, evidenced by a 1.661 WHIP and 10.6 H/9 in five appearances.

13. Candy Maldonado - 1 Year, $1.65 Million (1993)

Candy Maldonado spent his lone season with the Cubs when I was three years old so it's safe to say his tenure pre-dates my fandom. Although he spent just one year in Chicago, he definitely underperformed.

From 1986 to 1993, the outfielder put up a 110 OPS+ with the Dodgers, Giants, Indians, Brewers and Jays - establishing himself as a solid, if not spectacular contributor at the big league level. His career is full of pretty fun moments and he's bound to be an answer at barstool trivia - but his time with the Cubs was a total disaster.

After an .819 OPS (125 OPS+) with Toronto during their World Series season, Maldonado came to Chicago in 1993 and proceeded to fall flat on his face. Tasked with filling a spot on the roster previously held by Andre Dawson, it was an uphill battle from the start, but he did himself no favors with his performance.

Maldonado batted a woeful .186/.260/.286 line (48 OPS+) in 70 games with the Cubs. Somehow, Chicago managed to cut ties, trading the veteran outfielder to Cleveland in exchange for Glenallen Hill. He, of course, was best known for hitting a home run onto a rooftop across Waveland Ave, was stellar in his two Cubs stints (93-94, 98-00), putting up a .906 OPS on the North Side.

12. Willie Greene - 1 Year, $395K (2000)

Again, most of the lower-ranking players on this list, thankfully, were short-term signings that didn't significantly derail bigger picture plans. Willie Greene fits the bill in that regard. In the final year of his nine-year MLB career, the former first-round pick didn't bring much to the table, managing just a .654 OPS for the 2000 Cubs.

Instead of emerging as a third base solution for Chicago, Greene just never figured it out - despite being just 28 years old - and after his disappointing season, he never played another big league game.

Of course, the entire 2000 Cubs team was pretty disappointing, losing 95 games. Really, this roster was Sammy Sosa and company. The former NL MVP put up a 161 OPS+, but only he and Mark Grace played more than 100 games with an OPS+ north of 100. A disappointing offense and lackluster pitching staff culminated in a forgetful season in Wrigleyville.

11. Jacque Jones - 3 Years, $16 Million (2006)

After batting north of .300 in a couple seasons with the Twins a few years prior, there was cause for optimism when the Cubs inked outfielder Jacque Jones in Dec. 2005. Signed to a three-year, $16 million deal, the veteran handled right field duties for the team the following year, was a tick above-average with the bat and set a career-high with 27 home runs.

From there, things got shaky fast for Jones. There were rumors he sought a trade, then he said he wanted to stay and that was a constant theme the entire 2007 season. Two separate trades that would have dumped Jones were shot down by ownership, leading the team to run out the clock on the outfielder that year, despite his poor performance on the field.

Jones' power evaporated that year. He hit just five home runs and fell below league average at the plate in terms of OPS+, was irritated with his role on the team and the writing was very much on the wall by season's end. That November, Chicago sent him to the Tigers in exchange for Omar Infante (talk about a guy you don't remember being a Cub - although it's understandable since he changed hands again that very offseason, thus never setting foot on the field for Chicago).

He played one more year in the big leagues, splitting the 2008 season between Detroit and Florida, but hit just .147/.239/.207 in limited action. It's safe to say Jones' time with the Cubs didn't go as planned and he was one of those guys who just never seemed comfortable in Chicago. (And let's not even get into his post-playing days off-field revenge porn incident).

10. Kosuke Fukudome - 4 Years, $48 Million (2008)

It really bothers me to include Kosuke Fukdome on this list, because he wasn't a bad player by any stretch. But Cubs fans saddled him with what were probably unrealistic expectations fron the get-go, driven partly by the success of Ichiro Suzuki and Hideki Matsui and some monster years in Japan prior to coming over to the U.S.

His Opening Day 2008 performance - a game-tying, three-run home run in the ninth at Wrigley - raised those expectations even further. A strong first-half performance earned him his first and only All-Star selection, but he faded hard down the stretch (.639 OPS post-All-Star Break).

The following two years, he was a strong on-base presence in the Cubs lineup (.373 OBP in 1,032 PA) but he was never the transformational offensive addition fans hoped for. After a slow start to the final year of his contract in 2011, the Cubs traded Fukudome to Cleveland for a pair of prospects. What he's done in the years that have followed, though, is what's really remarkable.

Well into his 40s, Fukudome continues to play in Japan. He's not what he once was, but that's hardly a surprise given his age. This is a guy who was always a fan-favorite, even if he might not have been the franchise savior we'd once hoped for.

9. Todd Hundley - 4 Years, $23.5 Million (2001)

The biggest thing Todd Hundley had going for him when he signed with the Cubs in Dec. 2000 is the fact he was the son of the most popular and well-known catcher in franchise history, Randy Hundley.

That added a lot of excitement to his signing, which disappointed almost immediately. There was drama over who was getting reps behind the plate between Hundley and Joe Girardi early in the year and the former did himself no favors at the plate, batting .167 on the year. That marked a stark contrast from what he'd done in years prior, given from 1996-2000, he averaged 24 home runs and an .860 OPS.

He improved, marginally, in 2002, but still fell well short of expectations and didn't even finish out his contract with the Cubs. Incoming GM Jim Hendry shipped Hundley to the Dodgers in Dec. 2002, adding two key pieces of that 2003 team in Eric Karros and Mark Grudzielanek.

The deal, in and of itself, did nothing to solidify the catching situation in Chicago - but at least the front office managed to turn it into something to help the team win before it was all said and done.

8. Gary Gaetti - 1 Year, $2 Million (1999)

For some time there in the 1980s, Gary Gaetti was a dude. From 1986 to 1988 in Minnesota, he had a 125 OPS+, earning three consecutive Gold Gloves and an All-Star selection. He ebbed and flowed from there, trending back up in the mid-90s with Kansas City, earning his first Silver Slugger at age 36 in 1995.

After the St. Louis Cardinals cut ties with him in Aug. 1998 (to make room for the signing of Fernando Tatis), the Cubs pounced and added Gaetti for their stretch run with an eye on the postseason. The then-39-year old delivered in every sense, slashing .320/.397/.594 as the club chased down the NL Wild Card in September.

His contributions led to Chicago bringing him back into the fold on a one-year contract for the 1999 season and it quickly became clear Gaetti had caught lightning in a bottle the prior summer. He struggled to a .599 OPS in 308 trips to the plate and the Cubs let him walk at season's end. At age 41, Gaetti played his final big league season the following year, going hitless in just five games with the Red Sox.

6. Dave Smith - Two Years, $4.9 MIllion (1991)

The Dave Smith deal is a straight head-scratcher. Did the guy just run out of gas once he put his stuff in the Wrigley Field locker room? I can't make sense of it given what the right-hander did in the decade prior with the Astros.

From 1980-1990, Smith racked up 762 innings for Houston, notching 199 saves and working to a 2.91 FIP. He was the epitome of a bullpen anchor and, until Billy Wagner passed him, held the Astros' franchise save record. Then, he came to the Cubs on that two-year deal and the wheels just totally fell off for him.

After a disastrous month of April that ended with a trio of blown saves an an ERA in the 10.00 range, Smith settled in and made seven scoreless appearances in the month of May. But with each passing month from that point on, his ERA climbed higher and higher - capped by a 16.88 mark in four September appearances.

The final numbers? A 6.00 ERA in 35 appearances, a 1.758 WHIP and a 0.84 strikeout-to-walk ratio. Smith returned to the Cubs bullpen in 1992, the final year of his deal, but injuries kept him from returning to form and that marked the end of his big league career at the age of 37.

5. Nomar Garciaparra - 1 Year, $8.25 Million (2005)

There's a theme emerging here. Trading for a player midseason and his performing well down the stretch doesn't necessarily mean it's a good idea to bring him back again. This was the case with Neifi Perez around this very same time and the Cubs front office took the bait when it came to Nomar Garciaparra, too.

Acquired from the Red Sox in a four-team deal at the 2004 deadline, Garciaparra - once heralded as one of the top shortstops of his generation - but injuries took their toll, despite his continued success at the plate. Prior to coming to Chicago that July, the Boston shortstop had managed a .321/.367/.500 line, but appeared in just 38 games.

He hit well with the Cubs, posting a 109 OPS+ down the stretch. Upon hitting free agency that winter, the Achilles injury quickly quashed any chances of the infielder landing a long-term deal and he wound up coming back to Chicago on a one-year, $8.25 million deal. Those injury fears quickly proved to be very real, with Garciaparra hitting the shelf with a torn groin in late April.

Garciaparra hit decently well upon his return, finishing the year at a 97 OPS+ but appearing in only 62 games. The allure that came with trading for, then re-signing a former Rookie of the Year and two-time batting champion ended in bitter disappointment. Oh, and just to rub salt in the wound, he went to the Dodgers in 2006 and earned an All-Star selection. So that was fun.

4. Jeff Blauser - 2 Years, $8.2 Million (1998)

Hot on the heels of an impressive All-Star 1997 season with the Braves, Jeff Blauser came to Chicago ahead of the 1998 season looking like an answer at the shortstop position.

After all, the year prior, he tallied a 130 OPS+, a .405 OBP and 31 doubles for Atlanta, earning a Silver Slugger for his offensive exploits. But he fell well short of those expectations on the North Side, as his OPS+ plummeted to just 69 and his slugging percentage finished nearly 200 points lower than in '97.

Injuries didn't help matters for Blauser, who bounced back the following year with a 96 OPS+ but still hit just .240 on the year. He was limited to just 104 games in the final year of his deal and, before it was all said and done, was more of a role guy than an everyday starter.

The front office declined the option on the veteran infielder for the 2000 season and Blauser hung up his spikes after his disappointing time with the Cubs. Keep in mind the '98 Cubs carried a payroll of just $49 million, so paying Blauser just under 10 percent of that amount certainly did them no favors.

3. Edwin Jackson - Four Years, $52 Million (2013)

When we look back at the Theo Epstein era of Chicago Cubs baseball, it will always end in fond memories of the 2016 World Series and the washing out of a 108-year championship drought. But we also know that not every move was a home run and few missed at the level of the Edwin Jackson signing.

Before we delve into a deep chasm of disappointment, your fun fact about Jackson: he's played for more MLB teams (14) than any other player in baseball history. Love him. Hate him. Still a fun fact.

The 2013 Cubs were pretty not great, finishing the year at 66-96. Jackson, for his part, managed to lose a league-worst 18 games - but as we all should be well aware by this point, wins and losses are hardly the best way to evaluate pitchers. His 4.98 ERA was certainly unsightly, but a a 3.79 painted a more optimistic picture of his work. Regardless, a WHIP north of 1.400 isn't going to get the job done.

Things got decidedly worse in 2014 for the right-hander. Jackson allowed more than 10 H/9, battled control issues all year long and saw his WHIP climb even higher (1.642). By season's end, he was demoted to the bullpen - and no one had much faith in him being any better in 2015.

After losing his spot in the rotation early in 2015, Jackson once again headed for relief duty and was markedly more effective (2.91 FIP in 23 appearances). Still, looking for a clean slate, the Cubs designated him for assignment in July and cut ties with him shortly thereafter, eating the rest of his deal in the move.

2. Jason Heyward - Eight Years, $184 Million (2015)

The fact the largest free agent contract in Cubs history ranks this high on a list of the worst free agent signings in franchise history is hardly encouraging. But, hey, at least Jason Heyward's rain delay speech played a role in that Game 7 comeback in 2016, right?

Speech or no speech, there's no way to paint this contract as worth its weight. From the onset, Heyward couldn't figure it out at the plate. The fact he won back-to-back Gold Gloves in the first two years of the deal made things at least a bit more palatable, but his inabilty to replicate the offensive numbers from earlier in his career left a bitter taste in folks' mouths.

The year before coming to Chicago, Heyward put up big-time numbers for the rival Cardinals, slashing .293/.359/.439 - good for a 117 OPS+. That type of production, paired with his elite defensive work, made him look like a game-changer in free agency. But that hardly proved to be the case.

During his seven years with the Cubs, Heyward managed just an 86 OPS+. Late in the 2022 season, Chicago made clear its intentions to cut ties with the veteran - and he latched on with the Dodgers this winter via a minor league deal.

Production that fell well short of expectations and the fact his contract kept the front office from making necessary additions during the peak of the competitive window give Heyward the number two spot on this list, despite his outstanding contributions in the clubhouse and community.

1. Milton Bradley - 3 Years, $30 Million (2009)

Sure, Heyward was a major disappointment and drew the ire of fans for years - but at least he was a decent human being who provided at least some value, namely with his glove. The same cannot be said for the man who takes top billing on this list: disgraced outfielder Milton Bradley.

From the start, this marriage was doomed. By early summer, there was drama between Bradley and fans, the team's manager Lou Piniella and umpires around the league. That was just a sign of things to come. The outfielder put the organization itself and the media on blast in an interview in September and GM Jim Hendry suspended him for the rest of the season.

He never again played another game in a Cubs uniform. Chicago traded Bradley to Seattle that December after he slashed .257/.378/.397 in 124 games. The Mariners sent back right-hander Carlos Silva and cash in the deal, but it's safe to say that, no matter what, this deal was a complete and total failure by the organization and its biggest miss as far a free agency goes.