Tom Ricketts on ‘maybe the toughest’ season of his Chicago Cubs tenure: ‘Very, very disappointing’

The conditions are prime for postseason baseball, something Ricketts hasnt watched much of the last 10 days because he believes the Cubs should have made the playoffs, making Major League Baseballs first two rounds an unpleasant viewing experience.

During a wide-ranging conversation with the Tribune, Ricketts did not downplay how he felt about the Cubs again falling short of their goal.

Id have to say that of all the seasons, and I think Ive had 15 or so, this one is up there amongst the toughest, maybe the toughest, Ricketts told the Tribune.

Going into this season, expectations were high, and I believe that they were justifiably so.

Particularly relative to how the season ended this year, its been very, very disappointing.

What makes it the toughest is we knew we had a good enough team to be in the playoffs.

The Cubs had positioned themselves well for 2024 after falling short of the playoffs last year on the final weekend of the season.

The hiring of manager Craig Counsell and additions of left-hander Shota Imanaga and first baseman Michael Busch their production among the best at their positions during their rookie seasons were supposed to help get the Cubs over the top and back in the playoffs for the first time in a nonshortened season since 2018.

Instead, the Cubs again went 83-79 and didnt sniff the postseason, finishing 10 games back of the division-winning Milwaukee Brewers and six games out of the final National League wild-card spot.

A banged-up bullpen early in the season and a horrid offensive stretch from May through June put the Cubs in a hole from which they couldnt recover despite going 31-21 over the final two months.

President of baseball operations Jed Hoyer, who has been with the organization for 13 seasons, heads into a pivotal offseason ahead of the final year of a five-year contract he received when taking over for Theo Epstein before the 2021 season.

When questioned during his annual end-of-season news conference last week if he wants clarity on his contract, Hoyer said he looks at next year as an opportunity and feels the Cubs are in a great position.

Hes been a big part of all of our success that weve had over those years, Ricketts said.

I know Jed very well.

I trust him.

I really believe in him.

I think hes going to have good ideas for this offseason that will get us back on track.

Asked whether he expects to discuss a contract extension with Hoyer over the offseason or anticipates wanting to see how 2025 plays out before approaching that, Ricketts said, Hes under contract, thats the way I see it.

I think hes motivated, Ricketts said.

I know hes driven, like everyone else here.

He works really hard.

I think Jeds going to have a great offseason and put us back in the playoffs next year.

The Cubs possess some financial flexibility to improve the roster.

They are roughly $90 million under the $241 million competitive balance tax threshold for 2025.

A good chunk of that could be allocated to outfielder Cody Bellinger, however, if he picks up his $27.5 million player option for next year, which equates to $26,667,000 for the CBT.

Some players also have raises coming, including left-hander Justin Steele and third baseman Isaac Paredes in arbitration.

Ricketts said the Cubs are about in the same position financially as this year, adding, thats really Jeds responsibility to allocate those resources in the way he sees fit.

The Cubs ultimately were unable to stay under the CBT threshold in 2024, ending up approximately $280,000 over, according to Baseball Prospectus Cots Contracts .

The organization has typically stayed below the threshold except when adding a contract or two to make a playoff run, and this year obviously we tripped over it a little bit, Ricketts said.

The penalties on CBT, they grow over time and so you want to be careful when you do it, Ricketts said.

And so if theres ever some point in the future where theres a large financial commitment you want to make midseason, you have to be thoughtful about it.

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And really, if it was all money, wed win the division every year.

It really comes down to player development, getting the right people in the right chairs and hoping they all stay healthy.

The Cubs plan to play it by ear, Ricketts said, as to whether they will make sure to not exceed the CBT threshold in 2025 so the penalties reset.

You try not to go over in a year youre not going to make the playoffs, but every year is a little bit different, and well just cross that bridge where we see what the options are for the resources, he said.

Viewing 2025 through the lens of playoffs or bust isnt how the Cubs are approaching the offseason because, as Ricketts reiterated, reaching the postseason is an annual goal.

Cubs fans, though, are understandably becoming increasingly frustrated by the lack of recent playoff appearances, this years shortcoming particularly disappointing, something Ricketts often heard from fans he interacted with when walking around Wrigley Field during nearly every game.

His optimism for next season centers on the veteran core returning and younger players such as Pete Crow-Armstrong , who can be a game-changer, while the front office finds and acquires players that address the rosters weaknesses.

Not everything is bleak for the organization amid its journey to get back to the postseason.

The farm system features eight players in MLB.com s top 100 and leads all organizations, with seven of those Cubs prospects playing at Triple-A Iowa this past year.

The top-end talent gives the Cubs quality young depth heading into next season and potential leverage to acquire more proven big-league talent.

This feeds into the teams quest to create sustained success to be a perennial threat to win 90-plus games and make noise in the playoffs.

It all plays a part in the evaluation process as the Cubs work to bring another title to the North Side.

I feel like our future is really bright, and weve always looked to be consistent, Ricketts said.

We want to be one of those teams that consistently competes for the division, and the only way you can do that is to have a good system that develops players for you, and I think we have that right now..

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