Carter Hawkins continues a trend of recent hires by the Cubs from outside the organization which have been widely acclaimed throughout the industry. Among those hires: Dan Kantrovitz as VP or Scouting, Justin Stone as the Director of Hitting, and Craig Breslow as Director of Strategic Initiatives (who has since been promoted to Assistant GM/VP of Pitching).

Cleveland’s front office, especially their player development and scouting departments have a glowing reputation, but also a bit of mystery surrounding them. Their results are enviable however, especially on the pitching side (from Patrick Mooney and Sahadev Sharma’s article in The Athletic on the hiring):

It is always difficult to decipher who deserves credit and how much in situations like this. Scouting, player development, game planning, health and fitness, mental skills, and much more all play a role. Heck, luck does too. And no one person is responsible for results (good or bad). A note in favor of Hawkins influence is the fact Cleveland really never missed a beat, even after their front office was raided following their 2016 World Series appearance against the Cubs. Hawkins held a key scouting and player development role before, and even after being promoted to Assistant GM in recent seasons, always kept a hand in the player development side, which continued to produce for their organization in the wake of the changes.

It is expected Hawkins will work closely with VP of Player Development Matt Dorey on the continuing overhaul of the organization which began a couple of seasons ago. I know fans are over-anxious for results in that area, but it is important to keep in mind, the Cubs have been playing catchup, and unfortunately have been forced to cope with a pandemic while trying to implement new ideas. As a big market club with winning records over the previous six seasons, they were also limited in their bonus pools on the draft and international free agency fronts. Change was never going to be accomplished quickly, even under ideal circumstances, and the past two years have been far from that.

As GM, Hawkins will of course have a huge hand in the direction the Cubs take in terms of free agency and trades this offseason as well. A new voice, with new ideas from outside the org, should prove just as imperative there. But so to does the amount of resources available, and with that in mind, let’s turn our attention to the contents of the letter Tom Ricketts sent out to season ticket holders this past week.

In it, Ricketts makes certain financial promises, albeit vague:

Jed and the team are now focused on reloading our roster. We have the resources necessary to compete in 2022 and beyond, and we will use them. We will be active in free agency and continue to make thoughtful decisions to bolster our team this offseason.

This echoes statements made by President of Baseball Operations Jed Hoyer since the season ended. The Cubs plan to spend, but the claim is always couched by wording like “thoughtful” and “smart.” There is no doubt the team has plenty of payroll flexibility, but there is also no doubt there is little appetite amongst the fanbase for a long rebuild. The expectation has been set by clubs like Boston and New York that turnarounds can and should be quick for big market clubs after falling back to the pack.

Adding $100+M to their currently limited payroll commitments for next season is the bare minimum we should expect. Of course, a hundred million dollars doesn’t necessarily go very far when you need to completely overhaul a bottom five starting rotation, and at least replace a bit of the star power lost from the lineup at the trade deadline.

The Cubs do need to be thoughtful and smart in their moves this offseason. No one wants to see the club throwing money around without caution and end up with a couple of albatross contracts hanging around for the next five to ten years. But the Cubs can also take more financial risk than a smart small market team like the Rays, or even a smart mid market team like Cleveland. One bad deal won’t sink the Cubs the way it could for teams with fewer resources.

Hoyer, Hawkins and the rest of the front office do need to identify bargains on the free agent and trade markets. That means finding undervalued bullpen arms and minor league hitters like they did last offseason. It also means determining which of their prospects in an improving minor league system to hold, and which can be included in deals for proven (and/or undervalued) talent on other clubs.

But they also need to zero in on the proper targets at the top of the free agent market. Hitting on another Jon Lester-like deal for a free agent starter is imperative. Another John Lackey or Jason Hammel rather than an Edwin Jackson would go a very long way as well. While they’re at it, another Ben Zobrist is needed too.

This is going to be one of the more fascinating offseasons for the Cubs in recent memory. I’m glad they acted quickly to secure a new GM with a good reputation to help them set their course through this crucial time. If the right decisions outweigh the bad, the Cubs could rally from the bottom of the standing back into playoff and World Series contention in short order. Last weekend I couldn’t muster much enthusiasm even though I expected the Cubs to make a good hire, and spend some money this winter. Now, with the addition of Hawkins I feel more confidence with the group of decision makers in place, and though they are just words on a page at this point, I feel a bit more secure in the belief that the Ricketts family will give the front office enough resources to help turn this thing around.