Cubs Rumors: Pros and cons of going all in on a shortstop this winter

As the offseason presses on, the glaring question in the room is simple: Will the Chicago Cubs go all in on a shortstop this winter? If so, what is the damage going to be? After nearly record-breaking deals for Trae Turner (eleven years/300.0M) and Xander Bogaerts (eleven years/280.M), the question regarding the Cubs will be whether Jed Hoyer has the appetite to stomach a contract that goes against his moto of "spending intelligently." You have to break it down into a pros and cons list. There are several arguments to be had on both sides.

For one, you start with the obvious. Let's Analyze Dansby Swanson here, who seems to be the most realistic target for the Cubs at this juncture. What the first-year All-Star in 2022 brings to the table for the Cubs is upgrades both offensively and defensively. Furthermore, he is fresh off a Gold Glove after leading the National League in Outs Above Average with 21. He also led the entire league among shortstops with 16 runs prevented.

Pairing him with Nico Hoerner, who tied for second with Francisco Lindor in OOA and runs prevented in the National League, while sliding him over to the second base to bring in another elite shortstop gives the Cubs the best up-the-middle dynamic duo in baseball defensively. The Cubs' ability to turn double plays will be fantastic, especially as we venture into an era with the extreme shift being banned, putting even more emphasis on defense.

The first of the cons to address is that you're dedicating a monster salary annually to a player after just coming to the end of the Jason Heyward debacle. So, the taste in your mouth regarding long-term deals isn't particularly pleasant. Again, looking at Swanson, you love what you saw offensively this season. He had a career year at the plate, slashing .277/.329/.447 with a 116 wRC+ and .348 BAbip while accumulating an impressive 5.7 WAR.

The reason this is a con is that prior to Swanson's fantastic campaign, he had a career slash of just .249/.319/.409. To this point, 2022 acts as a ceiling for what we've seen out of Swanson's potential. Therefore, can the front office be sold that he will continue at this pace over the next several years or continue to improve? If the answer is no, you're setting yourself up for a contract that will crush you financially for years to come if he underperforms.

To counter that argument, the point can be made that if Swanson comes close to the numbers he put up in 2022, he helps immediately move the needle toward contention. The truth is simple. You can't afford to worry about contract structure 7-8 years down the road more than you're worried about winning right now when you have the resources to do so. The Cubs are a large market organization that doesn't need to take years to build a top-tier farm while incorporating a low-budget fielded team.

Chicago Cubs: If you want to win, you must adapt to the market.

Fans of the Cubs have supported the team through thick and thin. They deserve to watch meaningful games in October annually. If there's any belief that Swanson can continue to be a top-tier player in the league, then a long-term deal can't be what scares you away if you can bring a winning culture back to Chicago. The market is what it has become, and there is no way around it. Jed Hoyer has defined intelligent spending as signing someone who can help you now and later on while not hindering the team in the future.

For the shortstops on the market this winter, "intelligent spending" translates to missing out. All things considered above, the time is now for the Cubs to make a splash. Speaking of the farm, it so happens that the Cubs system is already ranked as high as 5th overall after a quick turn-around from the previous fire sale in 2021. They now have promising prospects at all levels, albeit with a lack of potential star power in the minors. The Cubs need a new face of the franchise that can lead them forward.

Nevertheless, you will not get a player on a team-friendly contract who has spent their whole career reaching free agency to secure a significant payday. If you don't want him, someone else will. Xander Bogaerts was projected for a six-year deal and wound up with eleven. Missing out stops you dead in your tracks unless you quickly pivot to the top remaining position players and hope for the best. Rolling the dice on a shortstop this winter is a gamble that can pay dividends but also drastically sets you back with any lack of judgment. When it boils down to having a crack at opening the window toward contention now, then It's better to swing and miss than not step up to the plate at all.

Signing a player to a lengthy 8-9 year deal should be independent of their production solely over the last couple of years on that contract if it means there's a chance to hoist a World Series trophy along the way. The Cubs have the opportunity to get their guy here. Although there is risk involved, there always will be when signing anybody. Ultimately, you can't get there if you don't go for it. The time is now to do just that.