With Most of Next Year’s Rotation Set, Cubs Could Target True Ace in Free Agency

The Cubs have an estimated payroll obligation of just $92.5 million for next season, meaning they’d have to spend about $54 million in free agency just to match this season’s mark. And $146.5 million is well below where a team of their financial stature should be playing, so it’s not unthinkable to project a baseball budget that affords Jed Hoyer $75-100 million to play with. Of course, it’s also possible he’ll be given much less than that and we get to hear Crane Kenney explain the nuances of rolled-over funds once again.

Regardless of how little trust you have in Tom Ricketts to once again open up his checkbook, the organization may finally be at an inflection point that necessitates spending more to earn more. Though many still talk about how Wrigley Field draws well in spite of the Cubs’ fortunes, a lot of those seats have been purchased at a steep discount on the secondary market. Season ticket sales have slid drastically and the marketing machine is working overtime to come up with promos to pull people in for anything other than the product on the field.

The new sportsbook is supposed to create a new revenue stream, but that feels like little more than a novelty play if the Cubs aren’t good enough to generate results worth betting on. Then you’ve got the rebuilt farm system that is ready to start churning out big league players, whether it’s for the Cubs or other teams that are willing to trade sure things for prospects. Follow the breadcrumbs and you can see how the path lends credence to what Ricketts said recently about spending again.

“Our moves over the past year and at the trade deadline have put us in a position of strength in both player and financial currency,” Ricketts said in a statement that echoed Hoyer’s phrasing. “We plan to be very active again this offseason competing in the free agent market.”

To be sure, even a very optimistic read here can’t conclude that the Cubs will indeed land a top shortstop, a lefty slugger, AND an ace, but Ricketts is being pretty specific nonetheless. With respect to time, I want to focus on the latter of those areas of need. Marcus Stroman and Kyle Hendricks will both be back next season, and both Justin Steele and Keegan Thompson have earned themselves spots in the 2023 rotation as well. That kind of foundation allows Hoyer and GM Carter Hawkins to tighten their focus just a bit.

They could further hone in while also increasing their margin for error by working out a deal to bring Wade Miley back for another go at it. Yeah, I know he’s only made four starts and he’ll be in his age-36 season, but there’s very little risk in giving him a one-year deal at the type of salary he’s going to command. Bringing him in might give the Cubs even more cause to swing big on a difference-making ace because they’d have enough depth to protect themselves in the event of injury or underperformance.

Just look at how this season has played out, with four of the team’s projected Opening Day rotation spending significant time on the IL. It’s also entirely possible we’ll see more six-man rotations and piggyback outings as the game continues to evolve away from workhorse starters. Might that help to mitigate the inherent risk of pursuing, say, Jacob deGrom?

The righty is the best pitcher on the planet when healthy, which is a problem because he’s had his share of injuries. He’s also turning 35 next year, so his body isn’t going to magically heal faster moving forward. Ah, but that age and injury history could work in the Cubs’ favor…sorta. We’re probably not looking at the kind of long-term deal Hoyer spoke last offseason about avoiding. In fact, he said quite plainly that the Cubs were comfortable with inflating the AAV on shorter deals à la Stroman.

You have to figure deGrom is going to want to beat Scherzer’s record $43.3 million AAV, and he might even be cool with doing it for the same three-year term. I’m thinking $150 million gets it done, but maybe $135-140 million with an opt-out after the second year — just like Scherzer got — works as well. That would put deGrom back on the market ahead of his age-37 season, which is exactly where his teammate was when he scored that mega-deal from the Mets.

Using the low end of what could admittedly be called a very optimistic budget, the Cubs would still have $30 million to spend in other areas. If Ricketts goes bigger, Hoyer could have another $55 million in addition to a whale like deGrom. That kind of money would turn things around in a hurry.

Another possibility Ricketts brought up is spending “player currency,” exchanging some of those top prospects for a pitcher who would slot in at the top of the rotation. Shane Bieber is going to get significant raises over the next two years of arbitration, but he’s still going to have much less impact on the bottom line than deGrom. He’s also seven years younger and would present a great deal less risk between both that and his salary.

Carlos Rodón is another fun name to throw out there, though the Giants will almost certainly scare the Cubs off by slapping him with a qualifying offer. Unless, that is, the Cubs give Willson Contreras a qualifying offer under the assumption that he’ll turn it down, thereby granting them a compensatory pick that more or less balances out what they’d lose by signing Rodón. That’s a risky move as well given the lefty’s injury history and likely contract needs, but maybe he’d like to be closer to his offseason home once again.

Rather than continue to prattle on by naming pitchers the Cubs should target, I’ll wrap this up by repeating what I noted earlier. The emergence of two homegrown starters allows the front office to narrow its offseason shopping list. And if Ricketts is serious about letting Hoyer peruse the aisles at Whole Foods rather than Aldi, this could be a very fun winter.

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