Chicago Cubs: What if these five things never happened in Cubs history?

Here we look at five significant events in Chicago Cubs history and think about what might have happened had they never taken place.

For years, it was a symbol of Chicago Cubs’ futility: Brock-for-Broglio. On June 15, 1964, the Cubs traded 25-year-old outfielder Lou Brock to the St. Louis Cardinals for pitcher Ernie Broglio. There were a few other players involved, but those were the two main pieces. It turned into a disaster for the Cubs.

In 2 1/2 years with the Cubs, Broglio won a total of seven games and posted a 5.40 ERA. Brock, meanwhile, collected 3,023 hits and 938 stolen bases, playing with the Cardinals until 1979 and ending up in the Hall of Fame. What if this trade never happened?

Brock wasn’t too impressive in his time with the Cubs between 1961-1964, batting .257 while not stealing bases nearly at the clip that he did in St. Louis. He exploded in the second half of 1964 with the Cardinals, batting .348 with 33 stolen bases in 103 games. Maybe he wouldn’t have done this in Chicago, but it’s fun to think about Brock on those late 1960s Cubs teams that were good but not quite good enough to make the postseason.

In that famous 1969 season, for example, center field was offensively one of the team’s weaker positions. Brock played center for the Cubs in 1962, but they moved him to right in 1963, and the Cardinals moved him to left, where he played the rest of his career. The Cubs, of course, had a great left fielder in Billy Williams.

Despite the speed, Brock holds a career defensive WAR of -16.8. He led the league in errors among outfielders seven times and was consistently below league average in range factor, meaning that he didn’t get to baseballs, nor did he field the ones he got to. This might be an indication that it didn’t matter which outfield spot they put him at, had they held onto him.

Still, given how good of a hitter he was, he would have been a welcome addition to those Cubs teams with Ernie Banks, Ron Santo, Fergie Jenkins, and Williams, among others, and he might have made a difference in getting them to the postseason.

This is just one of five hypotheticals in Cubs history we’ll look at here. Next up is a trade that worked out much better for the Cubs.

Chicago Cubs: What if they never acquired Ryne Sandberg?

As a Cubs fan, I like to see trades that work out well for them. Yet as a baseball fan in general, I want to see trades that work out well for both teams. And there’s a part of me that feels bad for the Phillies fans who are still bitter about the Ryne Sandberg trade. Putting my Cubs fandom aside, this has to be one of the worst trades in baseball history.

On January 27, 1982, the Phillies sent Larry Bowa and Sandberg to the Cubs for Ivan De Jesus. De Jesus had some decent years in the late 1970s but was coming off a 1981 season in which he put up an atrocious .509 OPS. The Phillies wanted to get rid of Bowa, yet only getting De Jesus for him alone was bad enough.

Throw in Sandberg – maybe not a top prospect but a pretty good one – and this trade just makes no sense from the Phillies’ perspective. But it got worse (for the Phillies): As we know, Ryno went on to be a Hall of Famer in a career that included ten All-Star selections, nine Gold Glove Awards at second base, seven Silver Slugger Awards, and the NL MVP Award in 1984.

Sandberg was a vital member of the division-winning 1984 and 1989 teams and may have made the difference. In 1984, the Cubs won their division by 6.5 games, and Sandberg put up a WAR of 7.1. In 1989, the Cubs won their division by six games; Sandberg’s WAR then was at 6.3.

Besides all that, had this trade never happened, we would have missed out on all the other great Sandberg moments until he retired for good after the 1997 season. Today, he remains one of the franchise’s all-time famous players. And it took highway robbery on the part of Cubs general manager Dallas Green to get him.

Chicago Cubs: What if the team had re-signed Greg Maddux?

Few things in Chicago Cubs history have stung more than letting Greg Maddux getaway. Arguably the greatest pitcher of his generation, Maddux came up with the Cubs in 1986 and, after struggling for a couple of years, put it all together starting in 1988. For the next five years, he started 176 games for the Cubs and won 87 games with a 3.01 ERA, culminating in winning the NL Cy Young Award in 1992.

Maddux departed for the Atlanta Braves and proceeded to win three more Cy Young Awards in a row while placing in the top five four additional times. Cubs general manager Larry Himes, though he got high marks for trading for Sammy Sosa, has been blamed for letting Maddux go. What if Maddux had stayed?

We can assume that those bad mid-1990s teams would have been better, but it’s not only because of what Maddux himself would have brought to the team. As a whole, the starting pitchers had to carry a lot more of the burden with Maddux gone. After posting a collective 3.21 ERA in 1992, that number went up to 4.45 in 1993 and 4.53 in 1994. Mike Morgan and Frank Castillo saw their ERAs go up significantly from 1992 to 1993.

Maddux came back to the Cubs from 2004-2006, but he was past his prime at that point. Had Maddux had his prime Atlanta years in Chicago, he would have quickly become the greatest pitcher in team history, surpassing Fergie Jenkins. Instead, all we can do today is wonder, what if.

Chicago Cubs: What if the Astros had drafted Kris Bryant?

The Houston Astros have been incredibly good over the past three seasons, winning over 100 games each year, two pennants, and a World Championship in 2017. (Of course, we now know that they were stealing signs, but that’s for another day.) What’s scary to think about is how they could have been even better had their top pick in the 2013 draft not turned into a disaster.

The 2013 draft was key for the Astros in their rebuild, as they had the first pick overall. They could have drafted Kris Bryant, considered to be the top hitter available, but instead, they went with Mark Appel, the top pitcher available.

Appel never made it to the majors. The Astros traded him to the Philadelphia Phillies following the 2015 season as part of their trade for Ken Giles, and he last pitched in 2017.

And as for Bryant, well, we know what happened: Rookie of the Year in 2015 and NL MVP and World Series Champion in 2016. He hasn’t been quite the same since then, but he’s still a solid major league player with lots of potential.

If the Astros had drafted Bryant, they might have been even better than they already have been, while the Cubs might have drafted Appel and missed. Given their inability to develop pitchers in recent years, it’s hard to envision them having much more success with Appel. Meanwhile, their struggles to find a quality third baseman – Aramis Ramirez from a decade earlier notwithstanding – would have continued. The Cubs got lucky on this one.