12 Baseball Lessons for Business After the Cubs’ Wild Card Sweep

Baseball lessons for business do not get much harsher than this: the Chicago Cubs entered the 2026 postseason with baseball’s highest scoring offense and best defense, then scored one run in 18 innings while the San Diego Padres led for 17 of them. Pete Crow Armstrong and Alex Bregman, two players at the center of Chicago’s hopes, combined to go 0 for 15 with eight strikeouts. The Padres won 8 to 0 and 4 to 1. Two games, two losses, season over.

I hated watching it.

I also could not stop thinking about it.

I live near Wrigley Field and attend roughly 30 Cubs games a year. Baseball is woven into the rhythms of my life. I love the strategy, the statistics, the tension, the strange humor, and the fact that a game can feel completely predictable until one pitch makes every prediction irrelevant. I have also spent more than 30 years building businesses, advising owners, hiring teams, making bets, absorbing losses, and trying again. Those two worlds speak the same language more often than people realize.

Baseball rewards preparation, but it does not promise a result. It celebrates individual brilliance, but nobody wins alone. It gives us enormous amounts of data, but still requires human judgment. It forces players to fail in public and return to the batter’s box anyway.

The 2026 Wild Card Series delivered all of that in about 48 hours. For Cubs fans, it delivered some pain too. Here are 12 lessons I am taking from it into business.

1. Past performance earns opportunity, not immunity

The Cubs had the highest scoring offense in baseball during the regular season. Their defense ranked first. Those accomplishments were real. They were also irrelevant once Game 1 started.

Michael King carried a no hitter into the seventh inning and finished with seven scoreless innings of one hit baseball. San Diego won 8 to 0. One night later, the Padres held Chicago to one run and completed the sweep.

Business owners can become attached to the résumé of the company. We had a record year. We built a great product. We have loyal customers. We hired talented people. All true, perhaps. None of it guarantees that the next campaign, launch, hire, acquisition, or sales quarter will work.

Reputation gets you into the game. Execution decides what happens after the first pitch.

The practical lesson is to measure present performance against present conditions. Do not use last quarter’s success as evidence that this quarter’s plan is working. Keep asking what the customer is doing now, what the pipeline is doing now, and what the numbers are saying now.

2. Details do not stay small

On August 12, the Cubs held a seven and a half game lead for a Wild Card position. They lost ground during the final weeks and slipped into the second Wild Card spot on the last weekend. That changed the location of the series. Instead of playing at Wrigley Field, they went to Petco Park, where the crowd was loud from the first pitch and the Padres looked completely comfortable.

One loss in August rarely feels like a crisis. One missed follow up rarely feels fatal. One late invoice, sloppy handoff, ignored customer complaint, or undocumented sales conversation may seem manageable. Then the small misses accumulate and change the conditions under which the important decision must be made.

The details are not separate from strategy. They are how strategy survives contact with reality.

A company can lose home field advantage without noticing. The warning signs are often ordinary: slower response times, declining conversion, unclear ownership, repeated exceptions, or meetings where everyone agrees but nobody leaves with a deadline.

Good leaders do not obsess over every detail personally. They build systems that make important details visible and assign someone to own them.

3. Preparation creates options

King’s seven scoreless innings in Game 1 did more than win that game. His performance protected San Diego’s best relief pitchers. In Game 2, when starter Nick Pivetta left in the fourth inning, Padres manager Craig Stammen could deploy Bradgley Rodriguez, Jason Adam, Adrian Morejon, and Mason Miller for the final five and two thirds innings. Those four relievers allowed only three men to reach base and did not surrender a run.

That was not improvisation. It was optionality created by preparation.

Businesses often confuse being busy with being prepared. Preparation means building cash reserves before the market slows. It means developing a second supplier before the first one fails. It means cross training people before a key employee leaves. It means knowing which expenses can be reduced and which investments must be protected.

The best time to create options is before you need them. San Diego entered Game 2 with a rested bullpen. A business should enter uncertainty with the same kind of depth.

4. Teamwork is not everyone doing the same job

Gavin Sheets spent much of September in a walking boot because of a plantar plate tear in his left foot. He was not available to play his usual defensive role. In Game 2, he came off the bench because the Padres believed his swing matched the moment. He hit a two run home run that turned a 2 to 1 game into a 4 to 1 game.

That is teamwork. It was not Sheets pretending he could do everything. It was a player understanding the contribution he could make, a manager choosing the right moment, teammates getting on base, and a bullpen finishing the job.

Business teams break down when every role is treated as interchangeable or when contribution is measured only by visibility. The person who creates the opportunity may not be the person who closes it. The employee who catches an operational error may create more value than the employee who presents the final result. The colleague who can contribute for one critical hour may matter more than the person who occupies the room all week.

Strong teams do not require identical roles. They require clarity, trust, and respect for how the pieces fit together.

5. Data should sharpen judgment, not replace it

The Padres knew Sheets could punish right handed pitching when healthy. They also knew the Cubs had Daniel Palencia on the mound, two outs, and a runner aboard. The matchup informed the decision. The manager still had to choose the moment, and Sheets still had to hit the pitch.

Atlanta provided another example in its decisive Game 3 against Philadelphia. The Braves used Ray Kerr, a 32 year old left hander with only 48 career appearances, as an opener because they wanted him against Kyle Schwarber and Bryce Harper. Kerr had missed most of the previous two seasons while recovering from Tommy John surgery. He responded with three and one third scoreless innings, allowing one hit over 47 pitches, 12 more pitches than he had thrown in any regular season appearance that year. Atlanta won 6 to 2.

The spreadsheet could identify the matchup. It could not guarantee Kerr would command his pitches under postseason pressure.

I believe in data driven decision making. I also believe data has to be interpreted by people who understand the context. Metrics can tell you where to look. They cannot always tell you what you will find.

In business, use data to challenge assumptions, compare alternatives, and define thresholds. Then apply judgment. A dashboard without judgment is a scoreboard without a manager.

6. A setback is an event, not an identity

Bryce Harper misplayed a fly ball in the seventh inning of Philadelphia’s Game 2 against Atlanta. The mistake helped the Braves build a two run lead. Cameras caught Harper alone in right field, thinking about what he would tell his son in that moment.

His teammates responded with encouragement. Cristopher Sánchez told him he was going to have a big moment. J.T. Realmuto told him, “You’ve got this.” In the eighth, Kyle Schwarber and Harper hit consecutive home runs to tie the game. Alec Bohm, who had made his own questionable defensive decision earlier, hit the winning home run in the tenth. The Phillies won 4 to 3.

That sequence may be my favorite lesson from the entire Wild Card round.

Healthy teams do not pretend mistakes did not happen. They also do not make the mistake the person’s identity. They address the play, preserve the person, and focus on the next opportunity.

A salesperson can lose a major account and still make the next call. A leader can make a poor hire and still improve the hiring process. A company can launch the wrong offer and still listen, adjust, and return with something better.

Accountability asks, “What happened, and what will we change?” Shame asks, “What is wrong with you?” Only one of those questions produces learning.

7. Perseverance works best when paired with adjustment

Andrew Painter began the season badly enough that Philadelphia sent him to Triple A on June 17 with a 7.06 ERA. He returned six weeks later, pitched his way onto the postseason roster, and delivered three scoreless relief innings in his first postseason appearance during the Game 2 comeback.

Painter did not persevere by repeating the same failing performance and calling it grit. He went down, worked, changed, returned, and earned a bigger moment.

Business owners sometimes use perseverance as permission to avoid a hard decision. They keep the same offer, process, vendor, employee structure, or pricing model because quitting feels weak. That is not always resilience. Sometimes it is inertia wearing a motivational shirt.

Real perseverance protects the goal while allowing the method to change. The mission may remain constant. The tactics should respond to evidence.

8. Depth beats dependence on a hero

The Yankees entered the postseason without Aaron Judge in the lineup. In Game 2 against Boston, Luis García Jr. hit an early home run. Max Fried allowed one run and three hits over six innings. The Yankees sent 10 hitters to the plate during a six run sixth inning. Cody Bellinger finished the rally with a three run home run after Boston intentionally walked Ben Rice to face him. New York won 9 to 2 and swept the series.

No business should be built around the assumption that its best player will always be available. That includes the founder.

If every important relationship belongs to one person, every decision waits for one executive, or every process lives inside one employee’s head, the company does not have a team. It has a dependency.

Depth requires documentation, delegation, coaching, and opportunities for people to perform before the crisis arrives. The Yankees did not replace Judge with one substitute superstar. They received meaningful contributions throughout the lineup and paired them with excellent pitching.

The goal is not to make talented people less important. It is to make the organization stronger than any single absence.

9. Momentum is built through repeated pressure

The Chicago White Sox entered the playoffs after three consecutive seasons with at least 100 losses. They also faced a Houston team that had beaten them five times in seven regular season meetings. None of that stopped the White Sox from winning 6 to 3 in Game 1 and 7 to 3 in Game 2, their first postseason series victory since 2005.

In Game 2, Chicago scored four runs in the first inning. Houston cut into the lead with three solo home runs, but the White Sox kept applying pressure. Chase Meidroth hit a three run home run in the sixth to restore the four run margin. Houston finished the series 0 for 9 with runners in scoring position.

Business momentum is rarely one dramatic breakthrough. It is repeated pressure in the right direction. One customer conversation leads to a better message. One process improvement saves an hour. One referral creates a relationship that produces another referral. Small wins become confidence, and confidence changes how a team responds when the opponent pushes back.

The White Sox did not erase three difficult seasons. They used what those seasons taught them.

10. Grace and accountability can occupy the same sentence

After the Cubs were eliminated, Bregman did not blame the schedule, the ballpark, or bad luck. “We didn’t play well enough,” he said. “It’s time to look in the mirror and get better.”

Craig Counsell acknowledged the pain without dismissing the good parts of the season. He said the Cubs had accomplished meaningful things and given fans joy, but they had not achieved their ultimate goal. He described the loss as part of the path rather than proof that the path had no value.

That is grace. It is honest without becoming cruel. It recognizes disappointment without converting disappointment into blame.

The best business leaders I know can hold two truths at once. We did good work, and the result was not good enough. The person made a mistake, and the person still deserves respect. The strategy failed, and the people who supported it were not foolish for trying.

Grace does not lower standards. It creates the psychological safety required to examine why the standard was missed.

11. Winning teams know when to celebrate and when to reset

After San Diego completed the sweep, the Padres celebrated. They had earned it. Then Xander Bogaerts turned his attention to Milwaukee and the challenge of facing Jacob Misiorowski. Manager Craig Stammen described the postseason as 13 bricks to lay. The Padres had laid two.

Some companies barely pause after a win. Others celebrate so long that yesterday’s result becomes tomorrow’s complacency. Both responses waste value.

A useful celebration does three things. It recognizes the people who created the result. It reinforces the behaviors worth repeating. It marks the transition to the next challenge.

Leaders should celebrate closed deals, successful launches, recovered customers, and difficult milestones. People need to know their effort mattered. Then the team needs a reset. The next opponent has already started preparing.

12. Never giving up does not mean never changing

Philadelphia’s Wild Card Series captured both sides of perseverance. The Phillies refused to quit in Game 2, overcoming a two run deficit with consecutive eighth inning home runs and winning in the tenth. One night later, Atlanta beat them 6 to 2. The Braves used an unconventional opener, attacked early with a three run Michael Harris II home run, and brought Game 1 starter Chris Sale out of the bullpen to strike out Harper with four sliders in the eighth.

The Phillies have now lost four consecutive postseason series despite a payroll reported at $322 million. At some point, perseverance has to include honest evaluation of the roster, the process, and the assumptions.

Businesses face the same distinction. Do not give up on a worthy mission because one attempt failed. Do not keep funding the same approach merely because you have already invested in it.

Persistence is a commitment to the outcome. Stubbornness is a commitment to the method. Good leaders know the difference.

A practical scorecard for business owners

The value of a sports metaphor is not the metaphor. It is what you do with it on Monday morning. Ask these questions about your company.

1. Which past success are we using to excuse weak current performance?
2. Which small operational details are quietly costing us home field advantage?
3. What options have we created before we need them?
4. Does every team member understand the contribution only they can make?
5. Which decisions should be informed by data, and where is judgment still essential?
6. How do we respond when a good employee makes a visible mistake?
7. Are we persevering intelligently, or repeating a method that evidence has rejected?
8. Where are we dangerously dependent on one person?
9. What small wins could create momentum this week?
10. Can we discuss disappointing results with both honesty and grace?
11. Do we celebrate wins in a way that reinforces the right behavior?
12. What should remain constant, and what must change?

If those questions feel uncomfortable, they are probably worth asking. If you suspect you may be chasing symptoms rather than causes, read Stop Solving the Wrong Business Problem.

Why baseball keeps bringing me back

Baseball is generous with second chances and ruthless about keeping score. A hitter can fail, learn, and return. A team can lose 100 games, rebuild, and win a playoff series. A player can misjudge a fly ball, then hit a home run in the next inning. A club can lead the league in runs for six months and discover that October owes it nothing.

That combination feels a lot like entrepreneurship.

Running a business means living with incomplete information while remaining accountable for the result. It means trusting people, measuring performance, changing plans, and returning after losses that felt personal. It means noticing the details without losing sight of the larger goal. It means understanding that resilience is a team skill, not merely an individual personality trait.

I wish the Cubs had given us a longer October. I wish Crow Armstrong had found a gap, Bregman had driven a ball into the seats, and the series had returned to Wrigley. That is the fan in me.

The entrepreneur in me knows disappointment can still be useful. The Cubs now have a clearer picture of what failed under pressure. The Padres showed what preparation, depth, matchup planning, and role clarity can produce. The White Sox demonstrated that a painful history does not get the final vote. The Phillies showed how quickly a mistake can become a comeback, and the Braves showed why leaders sometimes need to depart from the conventional plan. The Yankees reminded us that a team must be deeper than its biggest name.

Baseball does not promise that good preparation will always win. Business does not either. Both ask us to prepare anyway, pay attention anyway, trust the team anyway, and step back into the box after the last result hurt.

At Sanguine Strategic Advisors, we help business owners diagnose what is really happening, identify likely root causes, and evaluate practical paths forward before committing to a solution. Tell us what is happening in your business.

The Cubs’ season ended in two painful games. The lessons do not have to. Which one will change how you lead your team next week?

Related reading

• Stop Solving the Wrong Business Problem
• Before You Spend More, Get Your Marketing Strategy Right

Sources

• MLB: Cubs mull what could have been after abrupt Wild Card exit
• MLB: Padres win NL Wild Card Game 1
• MLB: Padres get revenge with commanding sweep of Cubs
• MLB: Padres bullpen deployed to perfection
• MLB: Phillies force Game 3 on three dramatic swings
• MLB: Braves finish off Phillies
• MLB: Phillies lose to Braves in NL Wild Card Series
• MLB: Yankees sweep Red Sox
• MLB: White Sox end 21 year wait with sweep
• MLB: Astros’ postseason ends with Wild Card sweep
• MLB: 2026 Wild Card Series matchups