The 162 game schedule is a big part of what makes Major League Baseball unique among professional sports in the United States because it tends to force differences in how games are approached throughout the season. No team is ever going to be undefeated, the current best team, the Atlanta Braves, has won a little over 65% of their games. The MLB season is a marathon meaning that in most cases a game is not treated as “must win.”

Oddly, while a long schedule means most games are not “must win,” for some teams, earlier than they would like, the season transitions to “it doesn’t matter whether they win or lose” because they are out of playoff contention. As a lifelong Chicago Cubs fan it has been my experience more often than not that the Cubs are out of playoff contention by the end of May or early June. Further, as a lifelong Cubs fan, I have learned it is much more fun watching games year after year when the team is playing meaningful games in September. I would much rather have the team lose in the playoffs every year than have the team out the playoffs by June in the majority of seasons.

So, in baseball, a transition occurs over the course of a season where teams move from playing to win games to playing to must win games. The benefit of expanding the number of playoff teams is that more teams start playing more “must win” games in September than in years past. In my experience, teams with players who have the most experience winning “must win” games are best positioned for long term success.

As an aside, it should be obvious why wild card teams, which have worse records than division winners, have had so much success in the playoffs, it’s because they usually play more “must win” games during the last month of the season and through that gain valuable experience and confidence. Turns out there is a big difference between “wanting to win” and “needing to win.”

At this point of a long 2023 season, the Chicago Cubs are starting the transition in to “must win” territory. Nobody associated with the Cubs is going to admit publicly that the games they are playing this week and next are must win, but it’s a mistake if they don’t start viewing the games as such, in fact they ought to embrace the transition. As Billy Jean King is often quoted as saying, “Pressure is a privilege.” The pressure of being in “must win” mode as the calendar flips from August to September is a badge of success.

The unpredictable nature of sports mean should the Cubs make the playoffs they could win the World Series. The probability of the 2023 Cubs winning the World Series is not high, not like it was for the 2016 team. However, the experience of playing as many “must win” games as possible over the course of the final month of the season is huge! The Cubs are exactly where they hoped to be at this time of the season and now players who have not had the experience with this type of pressure gain the experience that will provide dividends for years beyond.

I was mad the Cubs were crushed by the Brewers last night because I desire the immediate gratification of winning the N.L. Central this year, but I am happy that the young Cubs players such as their current best starting pitcher, Justin Steele, are getting this experience playing these games. However, the full value of that experience will not be realized if the team, from top to bottom, doesn’t consider these games “must win.”

The 2023 MLB Season is transitioning from “would like to win” to “must win” for the Cubs, and I am looking for the team to embrace the pressure.