The 1969 Cubs are a legendary team, regarded as one of the most cherished groups of players in MLB history that never captured a championship. Four core members who achieved Hall of Fame status are Ernie Banks, Billy Williams, Ron Santo, and Fergie Jenkins, alongside several others who enjoyed All-Star seasons and garnered affection from fans.
The well-documented reasons for their failure to win that year—or any year—are not the focus of this article.
Instead, this article will explore the actions of general manager John Holland, who assumed his role in 1957. I will highlight some trades he made—and some he chose not to make—that potentially deprived the team of players who could have propelled them to success in the late 1960s or early 1970s.
Tony Taylor
Tony Taylor was initially signed by the New York Giants in 1954, hailing from Cuba during a period when Cuban players were starting to leave a significant mark on Major League Baseball.
In 1957, the Cubs selected him in the Rule 5 Draft.
He became the team’s second baseman in 1958 at the young age of 22, concluding the season with a respectable .235/.299/.314 batting average and 21 stolen bases. While those numbers may not impress today, in that era, his 21 steals were the highest for any Cub since Stan Hack in 1940.
In 1959, Taylor enhanced his performance, achieving a 2.7 bWAR season with a .280/.331/.393 batting line along with 23 stolen bases—marking the most by a Cub since Augie Galan also recorded 23 in 1937. To illustrate how rare stolen bases were for the Cubs at that time, the entire team managed only 28 steals in the year prior, 1957. The stolen base revolution was on the horizon, but the Cubs overlooked this opportunity.
By 1960, Taylor was batting .263/.337/.421 over 19 games when the Cubs traded him along with Cal Neeman to the Phillies in exchange for Don Cardwell and Ed Bouchee.
Although Cardwell quickly made a splash with a no-hitter in his debut for the Cubs, he ultimately posted a 4.31 ERA across 111 games (93 starts) before being traded to the Cardinals in the Larry Jackson-Lindy McDaniel deal in 1963, which turned out favorably for the Cubs. Bouchee, who was an average defender at first base, had two lackluster seasons with the Cubs before being selected by the Mets in the expansion draft.
In contrast, Taylor had a successful decade with the Phillies, amassing a 17.6 bWAR and receiving MVP votes in 1963.
Had the Cubs retained Taylor, it is likely they would not have chosen Glenn Beckert in what was referred to as the “first-year draft” in 1962. Instead, they may have pursued another Red Sox prospect, Rico Petrocelli, who might have been chosen. Originally a shortstop, Petrocelli transitioned to third base and would likely have become the Cubs’ starting shortstop throughout much of the 1960s. In 1969, Petrocelli belted 40 home runs. If this scenario had unfolded, Don Kessinger might have transitioned into a valuable utility role or been traded.
Of course, all of this is speculative since the Cubs ultimately opted to trade Taylor.
Bill Henry
The Cubs acquired Bill Henry from the Red Sox in January 1957 in exchange for Frank Kellert, a backup first baseman who did not return to the majors after 1956.
That exchange proved beneficial. Henry delivered two strong seasons for the Cubs in 1958 and 1959, accumulating a 4.4 bWAR during the latter year. He led the National League in games pitched and struck out 115 batters in 135 innings, a notable achievement considering relievers were not expected to rack up strikeouts during that time.
In December 1959, the Cubs traded Henry, along with Lou Jackson and Lee Walls, to the Cincinnati Reds for “the other” Frank Thomas. Thomas had enjoyed a solid career as a power hitter in Pittsburgh throughout most of the 1950s, but was beginning to
By 1960, he was past his prime, finishing with a batting line of .238/.280/.399 and 21 home runs, leading to a trade to the Braves in early 1961 for a player you likely don’t recognize.
On the other hand, Henry earned a spot on the All-Star team in Cincinnati in 1960 and played a significant role in their NL pennant-winning team in 1961. Although he was nearly finished by 1969, he could have boosted the 1963 Cubs, who achieved a winning record. Regardless, they gave up a valuable reliever and received little in return.
Jim Brewer
Notoriously, Brewer was involved in a fight with Billy Martin, then a member of the Reds, in 1960. You can find more details here. Ultimately, the Cubs and Brewer sued Martin for over $1 million — a substantial sum at that time! — but the case was resolved out of court for $10,000 in 1968.
Brewer, who the Cubs had signed straight out of high school in 1958, spent four mediocre seasons with the team (5.66 ERA) before being traded to the Dodgers alongside Cuno Barragan in exchange for Dick Scott.
This was an absurd trade, especially considering Brewer’s success with the Dodgers. Scott was a 30-year-old journeyman who had gone through eight minor league seasons without a call-up until 1963, at which point he was 30. That year, he struggled in nine games for the Dodgers and made three appearances for the Cubs in 1964. Beyond that, all I can tell you is that he passed away in 2020 at the age of 86.
Conversely, Brewer enjoyed a 12-season tenure with the Dodgers, establishing himself as one of their most dependable relievers. He made one All-Star team, participated in three World Series, and accumulated 126 saves.
His contributions would have been beneficial for the 1969 Cubs.
Larry Dierker
At this point, you might be wondering, “Why mention Dierker? He never played for the Cubs.”
Yet, he very well could have. Cubs amateur scouts were monitoring him as a college pitcher at UC Santa Barbara. In that era before the draft, they offered him $35,000, while Dierker sought $50,000. He would have been worth the price, but the frugal P.K. Wrigley declined, prompting Dierker to sign with Houston, where he enjoyed a 13-season career with a 3.38 ERA and 25 shutouts.
In 1969, Dierker was a 22-year-old who won 20 games with a remarkable 2.33 ERA, achieving 20 complete games and four shutouts, earning him a spot on the All-Star team and placing 23rd in MVP voting. His bWAR that season was 8.7 — superior to any player on the 1969 Cubs (Bill Hands led with 8.4, and Fergie Jenkins had 7.2).
Dierker would have been an excellent addition to the Cubs’ rotation in 1969.
There are others, but you grasp the point. Decisions made and avoided in the 1960s cost the late 1960s Cubs some real talent. Those teams, especially the 1969 squad, had significant talent.
With better management, they might have evolved into a dynasty.
Unraveling the Cubs’ Missed Opportunities: How Management Decisions Shaped the Fabled 1969 Team
The 1969 Cubs: A Season to Remember
The Chicago Cubs’ 1969 season is often remembered as one of the most heartbreaking chapters in baseball history. With a talented roster that included stars like Ernie Banks, Ron Santo, and Billy Williams, the Cubs seemed poised to end their championship drought. However, a series of management decisions and missed opportunities ultimately derailed their hopes.
Key Players of the 1969 Season
The Cubs’ roster was filled with exceptional talent. Here are some of the standout players who contributed to the team’s performance:
| Player | Position | Batting Average | Home Runs |
|---|---|---|---|
| Ernie Banks | 1B | .250 | 23 |
| Ron Santo | 3B | .292 | 29 |
| Billy Williams | OF | .318 | 25 |
| Ferguson Jenkins | Pitcher | N/A | N/A |
The chemistry and potential of this team were undeniable, yet off-field decisions would prove critical in determining their fate.
Crucial Management Decisions
Several management decisions played pivotal roles in shaping the 1969 Cubs’ season:
1. The Trade Deadline Blues
During the 1969 season, the Cubs were in contention for the pennant but failed to make significant trades to bolster their roster. They had the opportunity to acquire key players who could have enhanced their chances, yet they remained inactive at the trade deadline. The reluctance to make moves, despite evident weaknesses in bullpen depth, proved to be a critical error.
2. Mismanagement of Pitching Staff
The Cubs’ pitching staff, while talented, was not effectively managed throughout the season. Manager Leo Durocher often relied heavily on his star pitchers like Ferguson Jenkins, resulting in fatigue and decreased performance during crucial late-season games.
3. Handling of Injuries
Injuries plagued the Cubs during the stretch run, yet management’s handling of these issues was questionable. Instead of seeking reinforcements or making strategic adjustments, they often stuck to their existing roster, which lacked the depth needed for a playoff push.
The Impact of the Mets’ Historic Rise
The 1969 season also saw the emergence of the New York Mets, who staged an incredible comeback to win the National League pennant. The Cubs’ failure to adapt to the rival team’s success was evident; management did not foresee the Mets’ potential and did not adjust their strategy accordingly.
Case Studies of Missed Opportunities
Several notable games throughout the season exemplified how management decisions directly influenced the Cubs’ performance:
1. The September Collapse
In September 1969, the Cubs had a commanding lead in the National League standings but went 8-17 down the stretch. Key games that could have secured the division title were lost due to poor pitching changes and lineup decisions.
2. The Doubleheader Disaster
A critical doubleheader against the Mets in September highlighted management’s shortcomings. After winning the first game, the Cubs fell apart in the second, showcasing a lack of effective defensive and offensive strategies that could have turned the tide.
First-Hand Experiences of the 1969 Team
Insights from players who participated in the 1969 season offer a glimpse into the internal dynamics of the team.
Ernie Banks’ Reflections
Ernie Banks expressed frustration over management’s reluctance to make trades that could have fortified the team. His leadership on and off the field signified the hopes of the franchise, and his insights provide valuable lessons on the importance of proactive management.
Ron Santo’s Perspective
Ron Santo’s experiences as a team leader highlight the emotional toll of the season. His comments on the pressure of maintaining a division lead reflect the burdens faced by players due to management’s decisions.
Benefits of Learning from the 1969 Season
Understanding the management decisions that shaped the 1969 Cubs can provide modern franchises with insights on how to navigate similar situations. Here are some benefits:
– **Strategic Planning**: The importance of preparing for the trade deadline cannot be understated. Teams must evaluate their needs and make proactive moves to strengthen their rosters.
– **Player Management**: Effectively managing player fatigue and injuries is crucial for maintaining peak performance, particularly in the late season.
– **Adaptability**: The ability to adapt strategies based on the performance of rivals is vital for any competitive team.
Practical Tips for Modern Management
Here are some practical tips for baseball management that can be gleaned from the Cubs’ 1969 experience:
– **Conduct Regular Evaluations**: Continuously assess team performance and identify areas for improvement.
– **Engage with Players**: Maintain open communication with players to understand their needs and concerns, especially regarding injuries.
– **Stay Informed**: Keep an eye on rival teams to anticipate potential threats and adjust strategies accordingly.
Conclusion
Reflecting on the Chicago Cubs’ 1969 season reveals the profound impact that management decisions can have on a team’s success. By examining these missed opportunities, modern franchises can learn valuable lessons that may guide them toward a more successful future. The 1969 Cubs remain a testament to the importance of proactive leadership in professional sports.
