The 8 Best And 7 Worst Chicago Cubs Since 2000

The last time the Chicago Cubs were in the World Series: Harry S. Truman was president, having just taken over for FDR, who'd died in office earlier that year; the ink had barely dried on the Japanese

The last time the Chicago Cubs were in the World Series: Harry S. Truman was president, having just taken over for FDR, who'd died in office earlier that year; the ink had barely dried on the Japanese Instrument of Surrender, effectively bringing an end to World War II; Bing Crosby was the biggest star in America, with his hit film The Bells of St. Mary's bringing in over $8 million at the box office; the league was still segregated, with Jackie Robinson more than a year away from making his debut with the Brooklyn Dodgers; and Bartolo Colon had just turned 30.

The last time the Cubs actually won a World Series: Teddy Roosevelt was nearing the end of his second term in office; the assassination of Archduke Franz Ferdinand of Austria, which would propel the events that would eventually lead to the first World War, was still five years away; and the first sound film, The Jazz Singer, starring Al Jolson in blackface, would not be released for nearly two decades.

To say that this season was a long time coming would be an understatement.

In honor of Chicago’s first trip to the World Series since 1945, and possibly their first World Series championship since 1908, we thought we’d compile a list of the 8 best and 7 worst Cubs players since 2000. The "best" was fairly easy, but the "worst" took a bit of thinking. We did our best to rank the worst, but, as Gertrude Stein, who passed away just a few months after the Cubs’ last World Series appearance (although, considering she was born just outside of Pittsburgh, we’re guessing she was more of a Pirates fan), would say, bad is bad is bad.

Here are the 8 best and 7 worst Chicago Cubs since 2000.

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22 Derrek Lee - BEST


First baseman Derrek Lee had a successful tenure with the Marlins before coming to Chicago, but it’s what he did in a Cubs uniform that established him as one of the best all-around players of the early 2000s. In his first season with the team, he hit .278/.356/.504 with 32 home runs and 98 RBI, but that was nothing compared to his sophomore season in blue pinstripes, when he led the league in batting average (.335), doubles (50), and hits (199), and swatted a career-best 46 home runs, all while playing Gold Glove defense.

In total, Lee spent seven productive seasons in the Windy City, compiling a batting average of .298 with 179 home runs and 574 runs batted in.

21 Jason Heyward - WORST

Richard Mackson-USA TODAY Sports

Jason Heyward has the dishonorable distinction of being the only player from the current roster to make the “worst” section of this list. Signed to an 8-year, $184 million contract, he was expected to play a big role in Chicago’s future, especially after he’d just come off arguably the best season of his career. But instead, so far at least, he has turned out to be a bust. In 142 games this season, he hit just .230 with a career-low 7 home runs and an on-base percentage of .306.

Despite his rough start, manager Joe Maddon has said that Heyward is still a “big part” of the team’s future. And at just 26 years old, there’s still plenty of time for him to turn it around in Chicago.

20 Aramis Ramirez - BEST


Playing on the opposite corner of the infield from Derrek Lee was Aramis Ramirez, who hit .294 with 239 home runs and 806 RBI in nearly a decade with the Cubs, establishing himself as the face of the franchise for the start of the post-Sosa era. He might not have put up the same gaudy numbers as Sammy had, but Ramirez consistently led the team offensively, with back-to-back-to-back 30+ homer seasons from 2004-2006, in which time he also hit .304 with 314 RBI.

The Cubs struggled after Ramirez left and Luis Valbuena took over at third, falling to a record of 61-101 in 2012, the second-worst record in all of baseball that year.

19 Sergio Mitre - WORST


Just going by the superficial stats (4-10, 6.12 ERA, 77 K, 47 BB, 120.2 IP), it might not seem like Sergio Mitre was one of the worst Cubbies of the century, but according to an interesting stat compiled by, where they determined the team record for games in which a player participated, the California-born pitcher was indeed awful.

According to Baseball Musings, in the 37 games in which Mitre appeared, 18 of which were as a starter, the Cubs compiled a win-loss percentage of .297, which is particularly awful when you consider that they had a total record of 256-230 (.527) combined over the three seasons in which Mitre was on the roster.

18 Mark Prior - BEST


Mark Prior’s name evokes equal parts joy and sadness amongst Cubs fans, because due to injuries, his greatness in Chicago was unfortunately short-lived. The second-overall draft pick out of USC made an impact with the team from the get-go, fanning 147 batters in 116.2 innings of work in 2002, finishing in the top ten for NL Rookie of the Year voting. He would follow it up with an even better sophomore season, compiling a record of 18-6 with an ERA of 2.43 and 245 Ks, putting himself not just in contention for the Cy Young Award, but for the MVP, as well, with a team-best 8.0 WAR.

Unfortunately, the rest of Prior’s career would be hampered by injuries, as he would only pitch in the majors for three more seasons. If not for his “Inverted W” arm action, which put undue stress on his elbow, there’s no telling what he could have accomplished in his career.

17 Koyie Hill - WORST


With a .355 batting average and 186 RBI in 198 games at Wichita State University, Koyie Hill was regarded as one of the top hitting prospects heading into the 2000 draft—ironic, given that his offense would be his biggest weakness in the majors, hitting just .207 with 8 home runs over 11 seasons, leading Chicago Magazine to label him a “perpetual backup.”

Hill joined the Cubs in 2007 after struggling to find a place within the Dodgers and Diamondbacks organizations, making his Wrigley debut after the infamous dugout altercation between Carlos Zambrano and Michael Barrett. He would go on to spend six years in Chicago, serving mostly as a second-string catcher and failing to live up to the expectations put on him as an amateur.

As a Cub, he put up a triple-slash line of .207/.266/.290, and from 2009-2011, he was considered one of the worst hitters in all of baseball according to weighted on-base average.

16 Kerry Wood - BEST


Along with Prior, Kerry Wood formed one-half of one of the most dominant pitching duos in the early 2000s. Together, they combined for 32 wins and 511 strikeouts in 2003, leading the Cubs to a first-place finish in the NL Central and a trip to the NLCS, which they lost in heartbreaking fashion in seven games to the Florida Marlins.

Like Prior, Wood struggled with injuries throughout his career, but was able to overcome them by making a successful transition to the bullpen, saving 34 games in 2008.

The highlight of Woods's time in Chicago came in 1998, when he tied fellow right-handed hurler Roger Clemens for the MLB record for most strikeouts in a single game with 20. In total, he struck out 1,470 batters in 1,279 innings in a Cubs uniform.

15 Edwin Jackson - WORST

Charles LeClaire-USA TODAY Sports

Edwin Jackson has had some good years in the majors—including a 2009 All-Star season wherein he went 13-9 with a 3.62 ERA, and a 2010 season that saw him throw a no-hitter—and some not so good seasons. Unfortunately for Cubs fans, his not so good seasons came in Chicago—and they weren’t just “not so good”; they were downright awful. Over three seasons as a starter and reliever, he compiled a record of 16-34 with an ERA of 5.37.

It’s hard to tell which season was worse: 2013, when he went 8-18 with a 4.98 ERA, or 2014, when he went 6-15 with a 6.33 ERA. It’s a real Sophie’s choice.

14 Jake Arrieta - BEST

Ken Blaze-USA TODAY Sports

Before joining the Cubs midway through 2013, it looked as though Jake Arrieta’s MLB career was destined for the gutter. As an Oriole, he had compiled a record of just 20-25 with a 5.46 ERA and a 1.472 WHIP. Since joining the Cubs, however, his ERA and WHIP have dipped considerably, to 2.52 and 0.985, respectively, and his wins and strikeouts have both more than doubled.

He won the Cy Young in 2015 after a masterful season on the mound, going 22-6 with a 1.77 ERA and 236 Ks in 229 innings of work. While his numbers have levelled off a bit this year and he struggled with his command at times, he still remains one of the best arms in all of baseball, as evidenced by his commanding performance against the Indians in Game 2 of the World Series.

13 Chris Volstad - WORST


The Cubs have had some of the greatest pitchers of the 21st century—such as Jake Arrieta, Mark Prior, Kerry Wood, Kyle Hendricks, Jon Lester, and Carlos Zambrano—but they’ve also had some of the worst. And perhaps the worst of the worst was Chris Volstad, who spent just one season in Chicago, starting 21 games and going 3-12 with a 6.31 ERA in 111.1 innings of work, striking out just 61 batters compared to 43 walks. Unsurprisingly, his 1.617 WHIP that season was by far the highest amongst starting pitchers on the team during the notorious 101-loss season of 2012.

12 Kris Bryant - BEST

Jerry Lai-USA TODAY Sports

Although just two seasons into his big league career, Kris Bryant has already proven that he is one of the best players in the game, taking home the Rookie of the Year award in 2015 after he hit .275 with 26 home runs and 99 RBI, and following it up with a potential MVP season in 2016, hitting .292 with 102 RBI and a team-leading 39 home runs.

If this is what Bryant is capable of before the age of 24, then Cubs fans have a lot to look forward to in the near future, especially with young talent like Kyle Schwarber and Anthony Rizzo rounding out the roster.

11 Todd Hundley - WORST


Todd Hundley was an interesting character. In just 1,225 games, he hit over 200 home runs, thanks in part to back-to-back All-Star seasons that saw him hit 41 and 30 homers, respectively. Outside of the long-ball, however, he didn’t add much in the way of offense, with a career .234 batting average. That .234 number, however, looks pretty appealing to Cubs fans compared to the .199 mark he put up in two seasons in Chicago.

True to his nature, he hit 28 home runs in 171 games, but struck out at a rate of nearly one K per game, falling far short of the .300 OBP mark. His tenure in the “City of Big Shoulders” wouldn’t have seemed so bad had then-GM Andy MacPhail not signed him to a sizeable (at the time, at least) 4-year, $24 million contract.

10 Anthony Rizzo - BEST

Jerry Lai-USA TODAY Sports

With six years of service under his belt, five of them with the Cubs, Anthony Rizzo is already looking like a seasoned veteran compared to some of his teammates—and he’s only 26.

Bryant and Rizzo had a friendly battle this season, the kind managers dream about, to see who could put up the best numbers at the plate. While Bryant edged out Rizzo in home runs, 39 to 32, Rizzo beat Bryant in RBI, 109 to 102, and they finished with identical batting averages and on-base percentages (.292/.385).

Even with his MVP-worthy season, however, Bryant still has a long way to go if he wants to surpass Rizzo as the team’s top player, especially when you consider that the lefty first baseman is one of only four players (including Edwin Encarnacion, Nelson Cruz, and David Ortiz) in all of baseball to hit at least 30 home runs in each of the last three seasons.

9 Neifi Perez - WORST


Before sabermetrics and the moneyball era came along, Neifi Perez enjoyed a comfortable, if underwhelming, career in the bigs, with a modest .267 batting average and a few accolades for his steady defense at short. But once statisticians started to dig a little deeper into the numbers, it was revealed that he was one of the worst players of his time.

For starters, his .267 average looks a lot less impressive when you consider that his on-base percentage was just .297 and he had a career offensive WAR of -3.8 (for reference, the highest oWAR all time is 155.1). Neifi was so bad that it led King Kaufman to create the “Neifi index,” which measures “the contribution a player makes to his team by not playing.”

So while Perez’s numbers with Chicago might look decent on the surface (.276 BA, 13 HR, 84 RBI in 264 games), you have to take them with a grain of salt.

8 Sammy Sosa - BEST


PEDs or not, Sammy Sosa is still the best Chicago Cubs player of the 21st century—maybe even of all time. In 18 seasons in the majors, he hit 609 home runs, 545 of which came in a Cubs uniform, and 238 of which came in a Cubs uniform after the year 2000.

Most will remember him for his 1998 season, when he battled Mark McGwire for the single-season home run record, ultimately losing out to the Cardinals slugger 70 home runs to 66, but Sosa arguably had his best seasons after the turn of the century, hitting a career-high .320 with a league-leading 50 home runs in 2000, only to follow it up with a .328 average and 64 home runs (his third 60-homer season) and 160 RBI in 2001.








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The 8 Best And 7 Worst Chicago Cubs Since 2000