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The window is just opening and should be open for a while, I’m not adding anyone on a multi-year deal that isn’t going to help extend that window - Sorry, MadBum - but wouldn’t hesitate to add older guys on one-year deals. The next wave - Alex Kirilloff, Trevor Larnach, Royce Lewis and a herd of young pitchers - is going to be here faster than anyone expected. And I trust most of the core that’s here now more than the guys that would command big money in free agency. Of course, the pitching rotation has to be addressed. Re-sign P Jake Odorizzi to a 3-year/$42 million deal. First up, Jake Odorizzi’s decision. By offering Odorizzi the Qualifying Offer, the team has seemed to identify him as someone they view as part of their core, or at least someone that could be part of their core. Accepting the offer is a simple way to guarantee $17.8 million in his pocket. It’s also a terrible way to guarantee future earnings, which is why I think Odorizzi says “no thanks” and searches for a three- or four-year deal. With draft pick compensation attached, I think that deal comes from the Twins. Something in the range of 3-years/$42 million sounds reasonable (could the Twins front-load his deal?) and I could see added language for a vesting fourth year included. A three-year pact lines up his free agency with the end of arbitration (at least for now) for all of Jose Berrios, Byron Buxton and Taylor Rogers. Add INF Travis Blankenhorn, P Dakota Chalmers, P Jhoan Duran, P Griffin Jax and OF Luke Raley to the 40-man roster. Five may be too heavy, but I view Duran and Chalmers as locks. Non-tender 1B C.J. Cron. Outright P Ryne Harper. Though the team has money to spend, committing in excess of $7 million on Cron is not something I’m comfortable with. I wouldn’t rule out bringing him back, but opening up a spot at first base gives the Twins more flexibility, whether that be for a different first baseman or moving Miguel Sano to first base and adding a third baseman. Harper doesn't need to be outrighted at the same time, but I found a need for a 40-man spot later in the offseason and he's the odd-man out. Extend CF Byron Buxton (4 yrs/$32m) and LRP Taylor Rogers (4 yrs/$24m) Though signing guys to extensions shouldn’t be the biggest news of the offseason, it should be a telltale sign of how the Twins view things going forward. The club needs to establish their core and lock them up. So far, they have done so with only Jorge Polanco and Max Kepler. I’ve never been a huge proponent of extending pitchers, so though I’d approach Jose Berrios about an extension, I wouldn’t put him in the extend-or-trade category. Byron Buxton and Taylor Rogers wouldn’t fit in that category either, but both should be pursued to sign contracts into their free agent years. The reasons are two-fold: These are core guys that can help extend the window. Both players, especially Buxton, could have their costs skyrocket. Locking them in at a set-cost helps establish a long-term plan for a team so aware of their financials. Eddie Rosario, and to a lesser extent, Miguel Sano, could both fall into the extend-or-trade category. Both have two years of control left. Both have clear ability, but obvious flaws in their game. There are prospects who will be ready soon that could replace Rosario’s production at a fraction of the cost. I fully expect Rosario to be traded this off-season, which we’ll look at later. If the Twins can hash out deals with Byron Buxton (4 yrs/$32m spread evenly, with two options), Taylor Rogers (4 yrs/$24m spread evenly, with an option), that would put in place two more important pieces of their core through 2023. Sign P Zack Wheeler to a 5-year/$95 million deal. (If you swing and miss, sign P Rick Porcello to a 1-year/$9 million deal.) Re-sign P Michael Pineda to a 1-year/$8 million deal. Re-sign RP Sergio Romo to a 1-year/$3 million deal. Sign C Stephen Vogt to a 1-year/$5 million deal. I anticipate the free agent market being slow. The big fish are all represented by Scott Boras, which means they aren’t coming off the board until very, very late. That’s likely to slow down the market for everyone else. Even with the assumed return of Jake Odorizzi, the rotation is still two starters short. As much fun as Gerrit Cole and Stephen Strasburg would be, they are going to require 6- or 7-year deals. Zack Wheeler might require a fifth year and the Twins should be willing to go that length. A five-year pact for $19 million annually is doable with the way the extensions have been formatted. If the Twins shoot their shot on Wheeler and miss, I wouldn’t look at any other longer-term deals. I’d shift my focus from signing one of the group of Michael Pineda (yeah, I would), Rick Porcello, Cole Hamels, Alex Wood and Homer Bailey to signing two of them. One-year deals with a team option preferable. While rolling with one-year deals on questionable starters during the clear window of contention seems counterintuitive, the moves that have been made previously have all ensured the window should stay open for, at a minimum, four more years. Making a long-term commitment to anyone - especially pitchers - comes with great risks as the results seem to decline rapidly on the wrong side of the 30… the age where most pitchers first hit free-agency. In addition to adding to the rotation, I loved what Romo brought to the bullpen and adding Vogt fills the backup catcher void, adds a good platoon partner for Garver and gives the team a tad more flexibility as he's played both 1B and LF periodically. Trade LF Eddie Rosario, P Blayne Enlow, INF Jose Miranda and P Luis Rijo to Miami for LP Caleb Smith and P Jose Urena. On the trade fronts, it’s simple: Zero in on controllable arms that can help for multiple years. Whether a sign of things to come or not, the Twins held on to their closer-to-the-majors pitching prospects, instead showing a willingness to trade on-the-cusp hitters and pitchers at the lower levels. There should be willingness to move Rosario and Sano if it can help accomplish the goal of moving the team both further into contention and to keep the window of opportunity open longer. In this particular trade, the Twins would be getting back a lefty for their rotation in Smith, who's controllable for four more seasons, and Urena, who could used in either a starting or relief role and who has two years remaining before free agency. That leaves a full 40-man roster and a 26-man/Opening Day roster that looks like this: Granted, Michael Pineda won’t count against either roster for the first six weeks of the season, that spot will be used on another young bullpen arm (such as Fernando Romero or Devin Smeltzer). Other things to consider: Marwin Gonzalez, Miguel Sano and Mitch Garver will split the shared at first base. Marwin Gonzalez and Jake Cave will be the primary left-fielders until Alex Kirilloff comes up (which he would, if I were in charge, in June). As you can see in the table above, Opening Day payroll is south of $120 million. By all forecasts, this is on the low end. This would allow the team to either (or both) shop free agents all the way until spring training (like they have done the last two years) and/or add payroll at the trade deadline. Additionally, the Twins would enter 2021 with around $58 million committed to a core of Wheeler*, Odorizzi, Rogers, Buxton, Kepler and Polanco. *Obviously, as previously stated, if the Twins miss on Wheeler and replace him with Porcello, payroll drops into the $106 million range, which allows additional flexibility when needed. The possible ways the Twins organization navigates the waters of this off-season are endless. But the reality is simple: the team needs to make moves that keep them competitive for the next half dozen years without sacrificing the payroll flexibility that they’ve established since Falvey and Levine took over. Check out these other Offseason Blueprints: Building a Bullpenner Hooking a Big Fish Making Big Betts ~~~ What would your blueprint look like for the Twins this winter? Download your copy of the Offseason Handbook and use it to construct a champion. Share your vision for discussion in our Create a Blueprint forum thread. Meanwhile, stay tuned to TD as our writers will be formulating offseason plans from different perspectives all week long.