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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St. Louis Cardinals –

The St. Louis Cardinals went from an exciting back and forth NLDS battle against the Atlanta Braves, to getting manhandled by the Washington Nationals’ starting rotation for four straight games and being dumped from the postseason pretty unceremoniously. The mismatch was pretty clear for the Cards, and it wasn’t because of their inability to hit the pitching of Washington. They lacked the shutdown postseason pitcher that could go toe-to-toe with a Max Scherzer or Stephen Strasburg. Madison Bumgarner could be that guy for them if they’re willing to spend the money to bring him to St. Louis. He isn’t the kind of lights out talent that’ll anchor a rotation for the length of the regular season, but that isn’t what you’re paying for if you’re the Cards. You’re looking to win the division again on the strength of your young talent, but then looking to thrive when you throw a playoff ace on the mound. Jack Flaherty could be that guy someday, but he isn’t yet. Bumgarner is, and for a St. Louis team who I thought was better than their NLCS sweep suggested, having a near guaranteed win in every third playoff game could be the difference in making it to the World Series or not in a pretty wide open National League.

Alternatives: Stephen Strasburg (RHP), Mookie Betts (OF), Francisco Lindor (SS)

Important Re-Signings: Michael Wacha (RHP), Adam Wainwright (RHP)

Milwaukee Brewers –

Perhaps the biggest heart break for me in the 2019 season was watching Christian Yelich go down with an injury a month before the season came to a close. Not so much because it hindered his back-to-back MVP chances, but because it exposed a Milwaukee Brewers lineup that seemed to flatline in the Wild Card Game against the Nationals. With Yelich in the lineup, Strasburg would have had to contend with another consistent threat, which would have opened the door up for mistakes to some of the other Brewer bats. As much as I believe that Milwaukee should address their rotation and bullpen this Winter, I think it’s far more important that they upgrade their lineup with another big time offensive threat. Didi Gregorius is a dream fit for the Brew Crew right now. He’s an immediate upgrade at Shortstop over Orlando Arcia, who has been unable to hit big league pitching consistently since arriving in the Majors. He provides another sturdy left-handed bat, to a Brewers team that has seemed to thrive when producing lefty-heavy lineups. Milwaukee will also likely be the beneficiaries of the Yanks minimal effort to retain Didi this offseason, because Gleyber Torres has proven himself to be the heir to shortstop in the Bronx.

Alternatives: Starlin Castro (INF), Francisco Lindor (SS), Jose Iglesias (SS)

Important Re-Signings: Gio Gonzalez (LHP), Eric Thames (1B/OF)

Chicago Cubs –

Add the Chicago Cubs to a sizable list of teams quickly falling from grace, but actively trying to find a way to stay competitive. They parted ways with Joe Maddon, siting his managing as the issue, as opposed to the play of the aging veterans that they’ve dished out overpays to recently. The Cubs can’t afford to spend any more money on their starting rotation this Winter, and I don’t see the kind of outfield help they need in this free agent class. So I think they should address the bullpen that’s given them trouble for years. Dellin Betances is a guy I’ve circled for them as a versatile piece in the pen, who will be surprisingly affordable after missing all of 2019 with various injuries. Most reports indicate that he’ll be ready to go on Opening Day, but washing away an entire year for a pitcher is never really a great thing. Still though, he’ll be able to work in any of the late innings for the Cubs, with his eyes fixated on the particularly elusive 9th inning job that he never inherited while with the Yankees. New York will likely be fixated on the big fish in the free agent pool this offseason, which will allow a team like the Cubs to pick off a piece of their lights out bullpen, without much of a fight.

Alternatives:  Mookie Betts (OF), Will Smith (RHP), Will Harris (RHP)

Important Re-Signings: Craig Kimbrel (RHP), Steve Cishek (RHP)

Cincinnati Reds –

I loved that seemingly out of the blue, the Cincinnati Reds went big in 2019, actively trying to trade their way into the postseason picture. They got shellacked down the stretch by their divisional foes, but I can appreciate the guts it took to take a shot at the playoffs the way they did. The contention window around homegrown superstar, Joey Votto, is quickly closing, so I wouldn’t at all be shocked to see the Reds retool and go at it one more time. Yasmani Grandal would be a great place to start. Stealing away the power-hitting catcher from the Brewers would not only weaken their divisional foe, but also provide them with the middle-of-the-order partner for Votto that they had hoped to find in Yasiel Puig or Matt Kemp last year. Grandal is a sound defensive catcher, and would be an instant upgrade over Tucker Barnhart who led major league catchers in past balls this past season, while also having the second most throwing errors by a backstop for the past two seasons. Barnhart can stay on as a backup, and thrive as a day-to-day pinch hitter, as he led the team in nearly all statistical categories during such opportunities in 2019. This would be a good first step towards immediate contention, an avenue Cincinnati is obviously quite fond of at the moment.

Alternatives: Salvador Perez (C), Travis d’Arnaud (C/1B), Jason Castro (C)

Important Re-Signings: Jose Iglesias (SS)

Pittsburgh Pirates –

The Pittsburgh Pirates finished last in the NL Central in 2019, but the season could hardly be deemed a failure. The Pirates were heavy participants in what was an utter dog fight in the division for the entirety of the campaign. Pittsburgh finished with a near .500 record against their NL Central rivals, having particularly strong success against the eventual division winner, St. Louis. That, plus the early breakout from Josh Bell, are indications to me that the Pirates are definitely on the right track, and with a few more pieces can be viable contenders in the Wild Card race, if not leaders in the division. I want a guy who’s already at his peak, but still under team control for at least another season or two. Kansas City’s Whitt Merrifield is that guy. The super-utility can slot in just about anywhere for Pittsburgh, and instantly provide the top of the order bat this team has lacked since the heyday of the Andrew McCutchen and Josh Harrison tandem. Merrifield could potentially be a costly trade to make, but Pittsburgh has the kind of minor league depth that the rebuilding Royals will find very attractive. If Pittsburgh can tailor a package around Oneil Cruz, a 6’7 shortstop who some scouts have compared to a slimmer Aaron Judge, could be just intriguing enough to a Kansas City squad that has no real timetable for their rebuild.

Alternatives: Jonathan Schoop (2B), Starlin Castro (INF), Didi Gregorius (SS)

Important Re-Signings: Francisco Liriano (LHP), Melky Cabrera (OF)