The offseason is officially upon us, and now a whole new level of excitement can kick in for every team and fanbase who has grown weary of the Washington Nationals victory parade already.

This Winter is sure to be an interesting one, with an upper echelon of talent that includes a man who is bound to set records as baseball’s highest paid pitcher…ever. Throw in the fact that pretty much every big name on the open market this offseason is represented by Scott Boras, and it becomes obvious that we’re also going to be in for a ton of painstakingly delayed signings (a la the Harper/Machado fiasco from a year ago).

Every team has needs this Winter though, and at least for the time being we can evaluate those needs and fantasy pair players with the teams we see as a good fit. That’s exactly what I tried to do here.

The rules of this piece are simple, only one player can be deemed the “must add” piece, regardless of how many pieces the team needs. This player can come via free agency, perceived trade options, or simply by re-signing an integral part of your current roster. Now since obviously all 30 teams in baseball have a need for a guy like Gerrit Cole, I went with the same rules that apply to real life: only one team can actually sign him. So for players who will draw big interest from several different organizations, I selected the team with the greatest need for them and who is most willingly to pay/trade the price.

So without further ado:

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New York Yankees –

It’s important to set the stage for the rest of this series by stating the obvious early: nobody needs Gerrit Cole more than the New York Yankees. Sure you can argue that teams like the Angels or Padres are feasible suitors with the purse strings and residency in his native So-Cal to lure the likely 2019 AL Cy Young Award winner, but a single stud-starter does not a contender make. Those teams both need to address a lot more than just an ace in order to be deemed playoff contenders, let alone prove to be the championship-caliber ensemble that Cole has become accustomed to pitching for. The Yankees need to bring in Gerrit Cole to fill arguably their only real weakness, which is a superstar starter the likes of which the Bombers haven’t seen since CC Sabathia’s early years in the Bronx. They have the all-potential arm of Luis Severino slated as one of baseball’s premier “Game 2” options, a solid 3 and 4 in James Paxton and Masahiro Tanaka respectively, and several feasible options for that final rotation spot with the returns of Jordan Montgomery and Domingo German next Spring. Cole’s a lifelong Yankees fan, so I can’t imagine that them pulling out all the stops to bring him to the Big Apple won’t be enough to see a new ace in New York on Opening Day. It’ll take a CC-esque type of overpay to make this happen, but after years of cost-cutting I think the Yankees are hungry enough for a championship to give Cole whatever he wants.

Alternatives: Stephen Strasburg (RHP), Corey Kluber (RHP), Noah Syndergaard (RHP)

Important Re-Signings: Brett Gardner (OF), Dellin Betances (RHP), Austin Romine (C)

Tampa Bay Rays –

The Tampa Bay Rays have long been a franchise hellbent on avoiding big payouts to anyone, whether that be a homegrown talent or a free agent, regardless on how incredible they might fit with the organization. Additionally, they’ve never been the type of team to roll the dice on a major acquisition via trade, especially if it entails giving up valued prospects. They’ll keep with those trends this Winter, angling to score a high-impact/cost-effective player at a position of need, Jose Abreu. The soon to be ex-South Sider is likely to be an early signee, as he wastes no time watching the market. The fit is obvious, with the Rays needing the offensive uptick at either first base (where Abreu is decent) or the DH slot (much more bang for your buck). There isn’t a big talent pool at first base or DH to choose from this Winter, but there also aren’t a ton of contenders actively trying to upgrade either slot. The Rays are probably able to get a good deal on a veteran eager to jump ship to a contender.

Alternatives: Edwin Encarnacion (1B/DH), Didi Gregorius (INF), Mike Moustakas (INF)

Important Re-Signings: Avisail Garcia (OF), Travis D’Arnaud (C/1B)

Boston Red Sox –

It’ll be a very interesting Winter for both the organization and their fans, as neither is accustomed to the concept of cost-cutting or intentionally balking at re-signing a home grown superstar. But that’s exactly where the Red Sox find themselves at the moment, with Mookie Betts likely to be shipped out of Fenway as the Red Sox have been unable to get him to recommit. Should they move Mookie, or J.D. Martinez, or both, they’ll pull in a sizable crop of prospects that’ll go a very long way towards re-seeding an otherwise barren farm system. In an effort to continue to contend in the immediate future, the Bo-Sox are going to need to angle themselves a cost-effective reliever with closer-potential. Ex-Yankee Betances is probably out of their price range, so they’ll turn to another in-division talent, Ken Giles. The former Astros closer is entering the final year of his contract and has had a slew of elbow concerns since the Summer, so he won’t exactly be a cashcow for the Toronto Blue Jays that will likely part ways with him for a MLB-ready starter whose ceiling is probably the backend of a rotation and a serviceable position player. I like Bryan Mata or Tanner Houck (neither of whom are valued particularly high by Boston at the moment) and Sam Travis (a 1B/DH who has yet to establish a hit tool at the big league level).

Alternatives: Will Harris (RHP), Sergio Romo (RHP), Jose Abreu (1B/DH)

Important Re-Signings: Mitch Moreland (1B), Brock Holt (UTL), Oscar Hernandez (C)

Toronto Blue Jays –

The team from up North has what everyone else in baseball wants, an exciting young core with tremendous upside. Now is their time to start swapping pieces in and out around that core to ensure that this is a championship contender within the next 5 seasons. The Blue Jays are going to try and bolster their rotation with young controllable arms, and since that’s not a realistic free agency find, they’re going to be involved in talks for a number of trade candidates around the league. After unloading what is probably their best trade piece to Boston for a back end starter and used-to-be-valued first baseman, they’re going to have to get creative in the marketplace to reel in their next pitching get: Matthew Boyd. The Detroit Tigers’ lefty gave the baseball world a glimpse of what he could do, pacing the junior circuit in ERA through May, before something of a misstep led to an abysmal rest of the year. Boyd is 28 years old and entering his prime, and with three seasons of team control through his arbitration years, the Blue Jays would be picking up another foundational piece who could realistically serve as a mid-tier starter when they turn towards contention. Boyd’s bad second half drops the price tag substantially, and considering the current state of the Tigers they’ll be happy to pickup a couple of immediate (albeit uninspiring) upgrades. I could see a package of Billy McKinney, Brandon Drury, and long-term catching prospect, Alejandro Kirk, being more than enough to get this deal done for Toronto.

Alternatives: Julio Teheran (RHP), Michael Wacha (RHP), Michael Fulmer (RHP)

Important Re-Signings: N/A

Baltimore Orioles –

The Baltimore Orioles should be looking at all of the teams listed above with unquestionable envy. The O’s haphazardly set out on a rebuild a year and a half ago, but have nothing to show for it yet in the way of fast developing prospects or opportunity-driven success from their current roster. Their most exciting talent in 2019 was the defense-only play of young center fielder Austin Hayes, but beyond that nobody else has shown that they’re capable of a tremendous leap. With little in the way of tradable assets, the Orioles best bet this Winter is to bring in a low-cost veteran with a desire for reinvention, and then flip him at the deadline or next offseason for more prospects. I like Michael Pineda for this role. He’s in desperate need of a clean slate, after injury-plagued years in New York and Minnesota that’ll be hard to forget about. But at 30 years old and with flashes of shockingly good strikeout stuff, he has some potential for reinvention that could prove vital to a contender down the line. The beautiful thing about pitchers, is that their statistical worth can be proven regardless of the environment they’re in. It doesn’t matter who follows them in the rotation or out of the bullpen, they can fully-control their own destiny on any given night. If Baltimore can ink Pineda to a team-friendly two or three year deal and get him to produce strong ERA and K/9 numbers in the first half of the season then they can use him to acquire more youngsters that fit their rebuild come July’s trade deadline.

Alternatives: Cole Hamels (LHP), Wade Miley (LHP), Jose Quintana (LHP)

Important Re-Signings: Jace Peterson (UTL)