But while I was researching that list, I also began compiling a list of the best player personnel moves in franchise history to complement the aforementioned worst list.
So as promised, here is the list of the best player personnel moves in Chicago Cubs history.
Hee-seop Choi was seen as the heir apparent to longtime Cubs first baseman Mark Grace when the club signed him out of the Republic of Korea.
For us Gracie fans, it was a punch to the gut when the news came out that the Cubs would not be re-signing Mark after the 2000 season. The blow was softened when he won a World Series title with the Arizona Diamondbacks in 2001, but it just didn’t seem right.
Prior to the beginning of that 2001 season, the Cubs brought in Matt Stairs via a trade with Oakland to serve as the bridge—along with Fred McGriff, who the Cubs acquired in a July 27, 2001 trade with the Tampa Bay Devil Rays—between Grace and Choi. They were to fill the role at 1B until Choi was ready to be called up and become the club’s regular first baseman.
The first part worked out for the Cubs: Matt Stairs and the Crime Dog came in and played okay for them—not spectacular, but solid. But the second part about Choi coming in and being their cornerstone first baseman for years didn’t quite work out.
Stairs left via free agency after the 2001 season, leaving Fred McGriff as the starting first baseman entering 2002.
On September 3, 2002, Hee-seop Choi was called up to Chicago and proceeded to hit .180 in 50 at-bats. But this wasn't seen as significant as the 2002 season was winding down and the Cubs were looking down the barrel of another losing season.
Choi began the 2003 season as the club’s starting first baseman in front of Eric Karros (who had been acquired in an offseason trade with the Dodgers, along with Mark Grudzielanek, for Todd Hundley).
Through May, Choi and Karros split time at first with Choi receiving more starts.
Then on June 7 while chasing an infield fly across the diamond with pitcher Kerry Wood also calling for the ball, the two collided violently. This sent the unconscious Choi crashing to the ground, with his head bouncing off the infield grass.
After that, Choi was never able to win back the starting role from Eric Karros.
Following the heartbreaking 2003 playoff run, the Cubs realized they need a long-term upgrade at first base. They dealt Choi to the Florida Marlins for Gold Glover Derrek Lee.
In Lee, they found a resemblance to Mark Grace on defense, a little give in average, but with more power and speed. As a Cub, Derrek Lee went on to win two more Gold Gloves and a Silver Slugger award.
When the Cubs signed Todd Hundley they probably thought they were getting an improved version of Todd’s father, and beloved ex-Cub, Randy Hundley.
Boy, they couldn’t have been more wrong.
A steroid-fueled Hundley set the then-MLB record of home runs by a catcher in 1996 with 41, and followed up that performance with 30 in 1997. Then after a 1998 season which saw him miss two-thirds of the year, he was traded by the New York Mets to the Los Angeles Dodgers.
In the 1999 and 2000 seasons at Chavez Ravine, he swatted 24 home runs in each season before becoming a free agent.
On December 19, 2000, he signed a 4-year, $23.5 million contract with the Cubs. A contract the Cubs soon came to regret.
Hundley’s stint in Chicago was not all rainbows and sunshine, but there was a bird flying.
After two tumultuous seasons in Chicago, Hundley was dealt for the second time to the Dodgers, this time for Eric Karros and Mark Grudzielanek.
Karros and Grudzie were integral pieces to the Cubs’ 2003 season and eventual playoff run. Karros was more important in June and July, while Grudzie's importance came in September and the few regular-season games in October, as he hit .359 and had 16 of his 38 RBI.
This trade with the Giants was a huge steal for the Cubs.
In Hundley, they received a player that would go on to become one of the most beloved Cubs players of all time, and one hell of a catcher.
Before Johnny Bench went on to win 10 consecutive Gold Glove Awards from 1968-1977, Randy Hundley won his only career GG in 1967 when he caught 152 games and committed only four errors.
He was a great field general and a team leader. Fergie Jenkins once said of Hundley:
“Having (Randy) Hundley catch for you was like sitting down to a steak dinner with a steak knife. Without Hundley, all you had was a fork."
Randy Hundley is credited with revolutionizing the catcher’s mitt to the type we see today by being the first to introduce the modern-day hinged mitt, which he helped popularize in the late 1960s along with Johnny Bench.
While with the Cubs, Hundley became the first major league catcher to use a hinged mitt, which enabled him, with no runners on base, to catch pitches with one hand, thereby protecting his bare hand from injury. Bench is often credited as being the first catcher to use a one-handed catching style, but it was Hundley who was the actual pioneer. Bench later adopted the Hundley style, perfecting the practice.
Bill Hands, on the other hand may not have had such a big impact on the organization or baseball as Hundley did, but he did win 20 games for the 1969 Cubs—arguably one of the best teams not to win a World Series.
Some “lifelong” Cubs’ fans (or those who've followed the team since 2003) may only remember Sosa’s toenail injury and corked bat incident of that season. Or the 2004 season and his refusal to lay off pitches located in the dirt of the left-handed batter’s box. Or his sudden inability to speak the English language on Capitol Hill to be unable to understand why this trade was one of the best in Chicago Cubs’ history.
But Sammy Sosa played an integral part in “bringing baseball back” along with Mark McGwire in 1998 with their home run chase, and this should never be forgotten.
On August 12, 1994, the Major League Baseball Players Association went on strike, erasing over an estimated 900 games, Tony Gwynn’s possible .400 season, Matt Williams’ run at Roger Maris’ record 61 home runs, a possible Montreal Expos World Series and a potential MVP season for Frank Thomas.
More importantly, they also erased the fans’ reverence for them and the game before ending the strike on April 2, 1995.
But even as the players ended their strike, the fans did not.
You could argue that it was in the fall of 1994 when football officially surpassed baseball as America’s favorite sport. And it would not be a losing argument.
Fans showed up to games early in the 1995 season to taunt the players and organizations. They threw money and garbage onto the field; berated the players; and many refused to come to games.
Cal Ripken Jr. began his own personal mission to return the game to its pre-strike prominence that season with his pursuit of Lou Gehrig’s streak of 2,130 consecutive games played. But the 1995 season posted nearly 20-million fewer fans than the pre-strike 1993 season.
In 1996 with sentiments for the game rekindled by Cal Ripken Jr., fans hesitantly returned to the ballparks with a league-wide attendance of over 60-million—10-million more than the abbreviated 1995 season.
Attendance level growth in 1997 did not match that of the season prior. In 1997 attendance grew by a mere 3-million fans.
Three years after the 1994 strike baseball was still suffering from the after effects.
Then came the magical 1998 season, and the home run chase between “Big Mac”, “Slammin’ Sammy," and “The Kid.”
Out of the gate Mark McGwire was hitting home runs at a historic pace followed closely behind by Ken Griffey Jr. Yet it took Sammy Sosa a couple of months to catch up.
Big Mac began the season with 11 home runs in March and April followed by 16 in May. Griffey as well had 11 home runs between March and April, but only eight in May. Slammin’ Sammy on the other hand started off slow by having only six home runs in April and seven in May.
When June began the home run chase was seen as a two-man race; but between Mark McGwire and Ken Griffey, Jr.
It was In June, however, that Sammy Sosa became the third horse in the home run race. That month Sammy slugged 20 home runs—the most HRs during the month of June in MLB history.
At the end of June, Sosa and Griffey both sat with 33 HR each and McGwire had 37. It wasn’t until after the month of July when the race heated up and the likelihood of two players breaking Roger Maris’ single-season home run record went from a possibility to a probability.
The home run chase captivated the entire country and Sammy Sosa’s performance, along with sensational rookie pitcher Kerry Wood, propelled the Cubs to the playoffs for the first time since 1989.
If that doesn’t do it for you, then how about 545 HR, 1414 RBI, and a career line of .284/.358/.569 as a Cub?
Full trade: Matt Bruback, Jose Hernandez and Bobby Hill for Aramis Ramirez and Kenny Lofton.
In this trade, the Cubs acquired two key pieces to their 2003 stretch run—Aramis Ramirez and Kenny Lofton—in exchange for, essentially, three contracts.
Both of these men played big roles in getting the Cubs to the NLCS.
Aramis Ramirez’s 15 HR and 38 RBI from the beginning of August through the end of the regular season and Kenny Lofton’s defense and .400 OBP to go along with 10 stolen bases in the same time span helped spur the Cubs to the N.L. Central Division title by one game over Houston and three over St. Louis.
More importantly, the acquisition of Aramis Ramirez finally solidified third base for the Cubs for the first time since Ron Santo was egregiously traded after the 1973 season.
Ramirez may not have been Ron Santo, but being labeled as the second-best player in club history at any position with an organization like the Cubs is an achievement in itself.
Full trade: Joe Carter, Mel Hall, Darryl Banks and Don Schulze for Rick Sutcliffe, George Frazier and Ron Hassey
This was a good trade for both teams. But the impact felt on either team by their key addition in this deal—Rick Sutcliffe for the Cubs and Joe Carter for the Indians—immediately after the trade and through their time with their respective clubs benefited the Cubs more.
After his acquisition by the Cubs in 1984 Sutcliffe went on to win 16 games in 20 starts with a 2.69 ERA and a Cy Young Award while helping lead the Cubs the NL Eastern Division title and the 1984 NLCS; he won his first start, but was also the losing pitcher in the series-deciding Game 5.
Again in 1989, Sutcliffe was a key piece to the Cubs winning their second NL Eastern Division title before losing to the San Francisco Giants in five games.
This was arguably the best free agent signing in Chicago Cubs history.
When the Cubs signed Andre Dawson he accumulated a Rookie of the Year award in 1977, six straight Gold Glove awards from 1980 to 1985, four straight Silver Slugger awards from 1980 to 1983, three All Star selections between 1981 and 1983, and placed second twice in NL MVP voting while with the Montreal Expos.
In 1987, his first season with the Cubs, “The Hawk” won the N.L. MVP—the third time in MLB history the MVP came from a losing team (Ernie Banks in 1958 and 1959); it has happened twice since 1987 (Cal Ripken Jr. in 1991 and Alex Rodriguez in 2003)—another Gold Glove, a Silver Slugger award and was again named as an All Star to go alongside 49 HR, 137 RBI, and a .287/.328/.568 stat line.
Through his six years with the Cubs, “The Hawk” had seasonal averages of .285/.327/.507, 125 OPS+, 29 HR and 98 RBI.
When inducted to the Hall of Fame in 2010, despite his expressed wishes as to which team would be emblazoned upon the cap of his plaque, Dawson entered Cooperstown as an Expo instead of his preferred Chicago Cub. Not only did he mean a great deal to the organization, the organization meant a great deal to him.
For the appreciation he showed the Cubs and their fans was only a microbe of the appreciation and admiration Cubs’ fans have for him.
This was hugely lopsided trade in the Cubs’ favor despite dealing away previous two-time 20-game winner Jack Taylor.
But their central return player, Mordecai Brown, went on to become one of the best pitchers in baseball history. Maybe not top five or ten, but in the history of baseball cracking the top 50 is incredibly impressive.
“Miner” Brown was the ace of the Cubs staff that, according to SABR researcher Cindy Thomson:
“With Brown leading an extraordinary pitching staff, the Cubs from 1906 through 1910 put together the greatest five-year record of any team in baseball history.”
He was part of the staff that led the Cubs to three straight World Series in 1906, 1907, and 1908, winning the latter two and again in 1910, losing to the Philadelphia Athletics.
But how good was he? Unable to find an eyewitness still alive who saw Mordecai pitch, we must rely on Al Gore’s invention to supply us with the correct information.
To begin with, in six of his first nine seasons with the Cubs he posted a sub-2.00 ERA; unheard of in this day and age.
Five times he had a sub-1.00 WHIP; again, unheard of today. He had a minimum of 20 complete games in his first eight seasons with the Cubs, and eclipsed 300 IP in 1908 and 1909.
From 1904 to 1912, his seasonal averages were: 21-6, 1.75 ERA, 23 complete-games, 253 IP, 2 HR allowed and a .992 WHIP.
Brown is the Cubs’ record holder in most wins in a season (29 in 1908), lowest ERA in a season (1.04 in 1906) and career shut outs (48).
During his career, Mordecai’s – and the Cubs’ – biggest rival was Christy “Big Six” Mathewson and the New York Giants.
Mathewson, just as Mordecai, is one of the best pitchers in baseball history – Baseball Reference has him listed as No. 5 on their EloRater. However, at one point Brown won over Mathewson on nine consecutive occasions, all of this after a June 13, 1905, loss in which Mathewson threw a no-hitter. The nine-game winning streak concluding on October 8, 1908—the game Mordecai called his greatest as noted in the previously-linked article by Cindy Thomson.
“But if one could ask him when his greatest game was, as many did when he was still living, he'd say October 8, 1908 at New York's Polo Grounds.”
The following is an account of that game taken from Ms. Thomson’s SABR.org post, infused with a short excerpt from her book Three Finger: The Mordecai Brown Story which will be highlighted in italics.
… The game was made necessary because of the 'Merkle Play.'
In the ninth inning during the September 23, 1908, game between the Giants and the Cubs, young Fred Merkle failed to touch second base on a play that should have scored the winning run for the Giants. Johnny Evers, remembering a similar play earlier when the call had not gone his way, solicited the ball Al Bridwell had hit. Whether he got that ball or another one is uncertain, but he stood jumping up and down on second base until he captured the umpire's attention.
Merkle was called out. Because the field was overrun by fans who thought the game was over, it was decided the game would be declared a tie, only to be replayed at the end of the season if it became necessary. It did. At the end of the season the Chicago Cubs and the New York Giants were deadlocked at the top of the National League standings.
Jack Pfeister started the game for Chicago, and Christy Mathewson took the hill for New York, a repeat of the Merkle game match-up. Mordecai had started or relieved in 11 of the Cubs' last 14 games so Manager Frank Chance decided not to start his ace.
**[This further angered Mordecai after already fuming from receiving threats from New York organized crime syndicate “Black Hand” to kill him if he pitched in the game.]
The crowd was enormous; some accounts put the total at 250,000 spectators, taking into account the throng outside the gates. While that number is highly unlikely, people did fill every available space inside and outside of the Polo Grounds, lining fence tops, sitting on the elevated train platform, and perching on housetops.
The Giants rocked Pfeister in the first inning, scoring their first run. Not willing to take any chances, Frank Chance called on Mordecai.
Pushing through the overflow crowd, Brown made his way in from the outfield bullpen [shouting] “Get the hell out of my way…here’s where you ‘black hand’ guys get your chance. If I’m going to get killed I sure know that I’ll die before a capacity crowd” and went on to win his 29th regular season game, securing the Chicago [Cubs] a third straight pennant and sending them on to play the Detroit Tigers and Ty Cobb in the World Series.
A short fun fact about Mordecai Brown and Christy Mathewson’s rivalry from BaseballHall.org: On Sept. 4, 1916, Mordecai Brown and Christy Mathewson faced each other in what turned out to be the final game of both their Hall of Fame careers.
**I added this statement to give context to the shortly followed The Mordecai Brown Story excerpt.
Full trade: Bob Buhl and Larry Jackson for Fergie Jenkins, Adolfo Phillips and John Herrnstein.
Not only did the Cubs receive an eventual Hall of Famer in this deal, they had to give up very little to do so.
The only notable statistic between Bob Buhl and Larry Jackson was the latter’s 24 victories in 1964 with the Cubs. The 1964 season was his only above-.500 season in Chicago despite a 2.55 ERA in 1963; even still he managed only a .500 record with the club at 52-52.
Ferguson Jenkins’ career, however, took a path different than mediocrity after the trade.
In his first six full seasons with the Cubs Fergie won—not averaged, but won—a minimum of 20 games per with an average ERA of 3.00, compiling 140 complete-games in that same time span.
In his first full season with the Cubs, Fergie won 20 games, pitched 20 complete-games, posted a 2.80 ERA and struck out 236 batters, which earned him an All-Star selection. Jenkins tied for second-place in Cy Young voting with Jim Bunning.
He won his only Cy Young award in 1971 with the Cubs—over the likes of Bob Gibson and Tom Seaver, and finished in the top-three in voting three consecutive seasons from 1970 to 1972—the only pitcher to do so during that time, and did again in 1974 with the Texas Rangers.
He is undoubtedly the franchise’s best pitcher in the live-ball era. Some would argue he ranks behind only “Three Finger” Brown as the organization’s best ever.
Regardless, Fergie is certainly one of the best pitchers in the long history of the Chicago Cubs/Orphans/Colts/White Stockings.
(Note: An earlier version of this story reported what the BaseballHall.org page said and claimed Jenkins was the only pitcher to accrue 3,000 strikeouts with fewer than 1,000 walks, but Maddux accomplished the feat as well and is the only pitcher to do so with 300+ Wins. An additional note: Curt Schilling and Pedro Martinez have both reached this achievement, too.)
A little background information from a 2010 B/R article by Josh Benjamin provides great detail of the trade.
Prior to the start of the 1982 season, the Philadelphia Phillies were just one season removed from their first World Series championship. They still had most of their core players, from pesky-hitting Pete Rose to the power bat of Mike Schmidt.
Yet, there was trouble in the clubhouse. Shortstop Larry Bowa and General Manager Paul Owens were unable to come to an agreement on a new contract and it appeared that the only option left was a trade. One team that showed an interest in Bowa was the Chicago Cubs.
At the time, the Cubs’ General Manager was former Phillies skipper Dallas Green, who had been at the helm for the team’s World Series run in 1980. With the Cubs in the hunt for a solid defensive infielder, he wanted Bowa. Yet, as Bowa was already in his mid-30s, Green also wanted a young infield prospect that could be groomed as Bowa’s successor. In fact, he had his eye on one particular player in the Phillies’ system: a young shortstop named Ryne Sandberg…Dallas Green insisted that Sandberg be included in the Larry Bowa trade. In return, the Phillies received infielder Ivan DeJesus.
That young prospect went on to become a nine-time Gold Glove-, seven-time Silver Slugger- and one-time MVP-winning Hall of Fame second baseman.
Ryne Sandberg was a beloved fan favorite and arguably one of the greatest Cubs of all time regardless of position.
One final note to conclude this two-part series: I did not consider draft picks nor amateur free agent signings when making this list—in case you wanted to know why Ron Santo was omitted from the list. Otherwise, his 1959 amateur free-agent signing would have been among the tie for first place.