2 realistic Chicago Cubs moves that could happen, 2 that won't with spring training approaching

The Chicago Cubs' payroll is just under $200 million. Owner Tom Ricketts has stated that the team's payroll is expected to rise just before the first tier of the luxury tax again. The team will be more mindful of not exceeding this season in efforts to reset after surpassing the mark a season ago. Going over for a consecutive year means a 30% tax on all dollars spent over the tax, and that's only if they land in the first tier.

Say what you will of the Cubs' spending habits, as fans beg for a major market team to act like one. The reality is that Jed Hoyer, his front office, and fans alike will have to accept that these are the parameters set by the Cubs chairman. With rumors persisting around every corner, the Cubs will do something else noticeable before the offseason concludes.

Gathering everything we've heard, let's look at the two most realistic moves, followed by two that have gained traction but don't make much sense before the start of spring training.

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Realistic: Ryan Pressly closes games for Chicago in 2025

The rumors have ramped up to the point that we now know a deal between the Cubs and Houston Astros that would send Ryan Pressly to the Cubs is in place. The hold-up is whether Pressly decides to waive his no-trade clause, but the fact is that he could greatly benefit from playing in Chicago on a contract year.

He is the setup man for Josh Hader in Houston but would slot into the closer role for the Cubs. If you're Pressly, with free agency a year away, that alone has to feel like perfect timing for an excellent opportunity to showcase what you can still provide to a ballclub, only upping his value for his next contract.

The downside is that Texas is home to Pressly, his wife, and two small children. However, if you're nearing a contract year and you may be in store for a change of scenery before long anyway, it may be wise to at least set yourself up as best as possible moving forward, as retirement likely isn't on the horizon at this point.

Realistic: If Pressly stays in Houston, David Robertson is a great fallback option

In the event that Pressly decides to stay in Houston, the Cubs will likely pivot to David Robertson, who the team has had a working relationship with for some time. In 2022, Robertson was the team's closer, and posted a 2.23 ERA before heading to Philly at the deadline in exchange for Ben Brown. Robertson may be 39 years old now, but still owns a 2.82 ERA over the last three seasons combined. His 3.24 FIP in that span indicates that he still has enough in the tank to be depended on.

Robertson has three 30+ save seasons under his belt, and is already familiar with the Cubs' front office and playing at Wrigley Field. If a reunion is in order, it will have to be after Pressly makes his decision on whether or not to join the Cubs. The three-year-younger Pressly's 2.97 FIP in the last three seasons indicates why he may be the priority, but Robertson is a solid addition to every ball club he joins.

Unrealistic: Jack Flaherty on a short term, prove it deal with opt-outs?

Undoubtedly, the Cubs want to keep their new superstar, Kyle Tucker, around after 2025. To do so, they must have enough funds cleared to make him a realistic offer. That means not tacking on multi-year deals that eat up payroll right now. Hence, there is an interest in Pressly and his final year or another reliever accustomed to signing one-year deals at this point in their career. With Jack Flaherty, the market has not quite materialized as he wanted it to after having a superb season between Detroit and Los Angeles.

Flaherty has dealt with a plethora of injuries and underperformance in the past five seasons. It was only in 2024 that he showcased his skill and could stay on the field for the first time since 2019. Therefore, he will unlikely receive the contract he seeks and may be forced to take a short-term deal with a player option after the first year, as we've seen with many recent players on a "prove it" deal.

If that is the case, the Cubs hypothetically have the payroll to add Flaherty and a reliever, but the risk is that if you're wrong and he underperforms or gets hurt, it prompts him to opt in next winter. That is a financial position that Jed Hoyer doesn't want to find himself in with Tucker's contract looming. With pressure on Hoyer to take the Cubs back to the postseason during his own contract year, he can't afford any critical mistakes. Flaherty's a nice get if he stays healthy, but the risk outweighs the reward for a team like the Cubs.

The biggest issue for Hoyer is the Cubs have several top 100 prospects that could help fetch them a sizeable return, like a frontline starting pitcher. However, If they do that, you're in a tricky position where you don't want to tack on more long-term payroll. Still, you also don't want to waste the entirety of your tradeable assets by acquiring somebody like Dylan Cease, who would only be around for one year. Money only for a one-year deal is the best way to improve the Cubs now and for the future, but any mishap could spell disaster.

Unrealistic: Cubs signing Alex Bregman

Although the Cubs could theoretically sign Bregman to a short-term deal, trade Nico Hoerner, and put top prospect Matt Shaw at second base, there's still the payroll issue. Bregman's AAV on a short-term deal will have to be higher than that of a longer deal, and that's where the plausibility of all this confuses me. He does not fit from a financial standpoint. Knowing the Cubs like to leave around $8 to $10 million for trade deadline acquistions, securing Bregman for nearly $30 million brings the Cubs to their comfort zone without addressing the bullpen.

The Cubs could use a proven third baseman with an All-Star track record on paper. However, the key word there is "proven," which Bregman has done throughout his career. Somebody will bite on the five-year contract he is looking for before long, and it certainly won't be the Cubs. Boston and Detroit remain the likeliest destinations, and it's rather ludicrous to imagine Bregman having to take a deal that could allow him to test free agency again next winter. That's the only way he'd come to Chicago, and even then, it leaves the team without addressing its significant need for a closer.