Chicago Cubs: biggest regret for 2026 off-season revealed
The Chicago Cubs are in danger of entering a serious free fall. They were just swept, at home no less, by the Milwaukee Brewers and now sit 1.5 games back of first place in the National League Central Division. Entering the series, the Cubs had won 15 consecutive games at Wrigley Field.
Now they are on a five-game losing streak. Aside from their two 10-game winning streaks this season, Chicago has a record of 9-21.
Indeed, much has gone wrong for the Cubs since the calendar turned to May. Several off-season decisions, for one reason or another, simply are not panning out.
The Chicago Cubs may regret signing Phil Maton the most

It is, of course, only May. However, the earliness of the schedule does not change the fact that some of the decisions Chicago made this off-season do not seem like good ideas in hindsight.
Among these was giving Phil Maton a two-year $14.5 million contract, a move Bleacher Report called the Cubs’ most regrettable decision of the off-season:
“Chicago decided this past offseason to sign another reliever who had logged the largest chunk of his innings pitched with Houston, bringing in Phil Maton on a two-year, $14.5M deal.
“It is not going well.
“Maton has an 8.78 ERA, and it wasn’t just an implosion or two. He has been tagged for multiple earned runs in six of his 15 appearances.
“What’s bizarre, though, is that he was almost untouchable in each of the three times he entered a game protecting either a one-run or two-run lead, yet to blow a save in 2026. Maybe the nonsensical solution is to only use him in save situations?”
Since the BR article was first published, Maton gave up a run in Chicago’s shutout loss to Milwaukee, raising his ERA to an even 9.00.
Simply put, $7.25 million is far too much to be paying a reliever who is giving up a run an inning. At the rate this is going, the Cubs may be forced to eat his contract by releasing him before it is over, or try to ship him off for a discount via trade.
More Chicago Cubs news from ChiCity Sports
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- Cubs urged to acquire intriguing pitcher amid free-fall
For More Chicago Sports
Follow me on Twitter at @theotherRobin19, and follow us @ChiCitySports23. You can also reach out to Robin Adams via email at robadams14@gmail.com. To read more of our articles and keep up to date on the latest in ALL of Chicago sports, click here! Chicago Bears, Chicago Bulls, Chicago Cubs, Chicago White Sox, Chicago Blackhawks
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Source: https://www.chicitysports.com/chicago-cubs-phil-maton-biggest-regret/
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