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OTM Roundtable: The Pick 5 Edition

We’re playing too. Sort of.

Atlanta Braves v Boston Red Sox Photo by Maddie Meyer/Getty Images

This is our last roundtable before the offseason officially kicks off, with the latest that being possible to happen coming next Thursday. And, as you may or may not have seen, we launched this winter’s Pick 5 contest this past week. If you want to read about that and enter, you can check that out here. I figured it would be fun for the staff to get involved this year, too. We’re not playing to win. That’s still just the readers who are eligible to that, but we each picked our five potential targets as well.

Michael Walsh

  • Jackie Bradley Jr.
  • Kevin Gausman
  • Tommy La Stella
  • Joakim Soria
  • Keone Kela

This group would fill all of the Sox’ needs at reasonable prices. Bradley keeps control over center field. La Stella presents a viable option over Michael Chavis and can play first. Gausman is solid as the third or fourth guy in the rotation. As for the relievers, Soria is a good veteran arm, and while Kela is dealing with a forearm injury, but has potential and should be cheap.

Shelly Verougstraete

  • Andrew Benintendi to Miami for Pablo Lopez and Jorge Guzman
  • Red Sox sign Trevor May
  • Red Sox sign Jake Odorizzi
  • Red Sox sign Michael Brantley
  • Red Sox sign Joe Panik (Tommy La Stella?)

Honestly, I would hate to see Benintendi leave, but at this point a change of scenery might be the best for him. Miami needs some help with their offense and always seems to have capable pitchers in their minor leagues. Jorge Guzman and signing Trevor May will bolster the downright dreadful bullpen. Jake Odorizzi, while he struggled with injury and ineffectiveness this year, is a perfect low-cost signing. I’ve always been a Michael Brantley (aka Dr. Smooth) fan and he could slide into left field if Benintendi. I could also see the Sox making a low-cost signing at second like Joe Panik or maybe spend a bit more for Tommy La Stella.

League Championship - Houston Astros v Tampa Bay Rays - Game Seven Photo by Sean M. Haffey/Getty Images

Keaton DeRocher

  • Kirby Yates
  • Marcell Ozuna
  • Robbie Ray
  • Raisel Iglesias
  • Clint Frazier

The Red Sox need a good reliever and Yates is coming off a down year, one year removed from being the best reliever in baseball. Taking a chance on the bounce back makes sense. Ozuna is probably self-explanatory but just in case: The Sox need an outfielder and he likes hitting in Fenway. Go for it. Robbie Ray would be a Nick Pivetta 2.0 move where he has really good raw stuff but just never put it together. It’s the kind of low-risk high-reward move we’ve seen Bloom make before. I already mentioned the reliever need and a swap focused on Benintendi and Iglesias makes sense if Bloom wanted to go that way. In a move that makes sense but will probably not happen, the Yankees have a bunch of outfielders and the Sox need one. It’s a chance for Frazier to get playing time.

Mike Carlucci

  • Joc Pederson
  • Brad Miller
  • Matt Moore
  • Alex Wood
  • Brad Boxberger

I’m thinking, like many GMs, Chaim Bloom will look to some former Rays players that he can bring around for a second run. It will be an offseason like 2012 seeking out smaller free agents from the bargain bin who under the radar. Given the need in the bullpen and low acquisition cost, Boxberger is a great target. Let’s do this, Bloom!

Phil Neuffer

I do not expect the Red Sox to spend big this offseason, which means I’m not banking on guys like Marcell Ozuna and George Springer. Since the high-profile names are where most of the attention and rumors tend to go, trying to determine more fiscally responsible transaction murmurs can be difficult. Therefore, I’m approaching this exercise by speculating off the cuff and picking players that would fill a need for the Red Sox and could be acquired without a huge spending push.

Joe Musgrove

John Tomase floated Musgrove’s name as a trade target earlier this week and I think that would make a lot of sense. Musgrove has been a perfectly capable starter for the Pirates, but he will be just 28 next season, so there’s potential for more. At worst he can help shore up the rotation; at best he can be a rising star.

Aaron Loup, Trevor May and Keone Kela

I’m grouping these three guys together because I think they all could be solid additions to the bullpen who wouldn’t completely break the bank, although they may have to spend a little extra for someone like Kela. There’s a whole list of similar relievers, but I’ll take my shot with these three.

Jackie Bradley Jr.

Matt asked us not to pick the players we want to be signed or be traded for, but I don’t care. If I write it down here, perhaps such positive thinking will make it happen. It feels unlikely, but I do think the Red Sox will add some outfield help at the very least. Bradley is my official pick, but if he chooses another route, maybe someone like Jake Marisnick.

Jake Kostik

So it feels kind of strange to have my own game (which I inherited from my forefathers) turned around on me, but I’ll do my best. I feel like the Red Sox are going to have a fairly muted off-season. While it is clear the fans are going to want the likes of Trevor Bauer and other big names, I feel like Chaim Bloom values the second and third round picks too highly to make such a move. If we were one Trevor Bauer away from being a playoff team (and we just might be, this was a weird year), then it becomes a very easy decision for me, but I don’t feel that it would be wise in our current situation.

So I’m left to look over the free agency list. I believe we will sign two starting pitchers, an outfielder, a backup infielder, and probably a few more relievers. With that said, I feel like these five would be my current picks: Jonathan Villar, Kevin Pillar, Jon Lester, Taijuan Walker, Keone Kela.

Jake Devereaux

  • Trade Andrew Benintendi, Gilberto Jimenez, Aldo Ramirez and Ryan Zeferjahn to the Cleveland Indians for Zach Plesac.
  • Sign Marcell Ozuna to a five-year deal worth $120 million dollars.
  • Re-sign Jackie Bradley Jr. to a three-year deal worth $36 million dollars.
  • Sign LHP Alex Wood to a one-year deal worth $5 million dollars.
  • Sign Asdrubal Cabrera to a one-year deal worth $3.5 million dollars.

The two big moves of the off-season are trading for Zach Plesac and signing Marcell Ozuna. Ozuna slots into Benintendi’s vacant spot in left field, Bradley resumes his post in center, and Alex Verdugo stays put. Alex Wood comes in on a one-year show-me deal as the Red Sox decline Martín Pérez’s option for 2021. Asdrúbal Cabrera takes over second base until 2022 when Jeter Downs is ready to fill the position. Jarren Duran will come up for a cup of coffee in September and by 2022 J.D. Martinez will be traded in the off-season clearing the way for Duran to take over in left and Ozuna to move to DH. By 2022 the Red Sox feature a rotation led by Chris Sale and Plesac as they capture the American League East Division for their first time since 2018.

Chicago White Sox v Cleveland Indians Photo by Ron Schwane/Getty Images

Brady Childs

This team’s behavior over the past year has conditioned me to expect them to be as cheap and as underwhelming as possible. Luckily enough, I have a long track record of doing my best predictions while being as nihilistic as possible. If that’s good enough for you, go bet this wicked parlay.

Jake Marisnick - a worse, but cheaper, version of Jackie Bradley Jr.

J.A. Happ - this team badly needs starting pitching and he’ll be cheap.

Julio Teheran - looked absolutely busted this year so he’ll be cheap.

Brandon Workman - he can come back to a team that knows him and he’ll be cheap after bombing in Philadelphia.

Jonathan Villar - being as nihilistic as possible means I’m assuming they trade Xander so they’ll need a body to stand there.

If you take this your local casino and win you owe me 40%.

Bryan Joiner

  • Marcel Ozuna
  • Michael Brantley
  • Shin Soo-Choo
  • Robinson Chirinos
  • Yoshi Hirano.

You’ll note that three of these are outfielders; I’m stacking the deck here so to speak, and I had a notion to put Jackie Bradley Jr. in there as well. Ozuna seems like he’s gonna be on every one of these lists, Brantley fits the profile to a T and so does Choo, at a lower pay grade. Obviously they need some outfield help, so I’m gambling that I’ve ID’ed the sort of player (and value) they want. Chirinos is just one or many possible catcher options but a good bat-first complement to Christian Vázquez and Hirano, at 37 years old, is another potential value signing in the Koji Uehara mold. It’s possible I put him in here just so I could mention Koji... imagine how often we’d all do it if they got him! I’m already happy.

Matt Collins

  • Jake Odorizzi
  • Chris Archer
  • César Hernández
  • Nick Senzel
  • Michael Brantley

I went over this list in the latest episode of the podcast, so I’ll be quick here. Odorizzi and Archer have the vaunted Bloom connection in Tampa Bay and should be relatively inexpensive with mild upside. Hernández has long been a personal favorite of mine and is a steady, inexpensive option at a position of need at second base. Senzel could fill the hole at either second or center and has seemingly fallen a bit out of favor in Cincinnati. That deal would be something involving Benintendi, though Boston would need to add more. And Brantley would only make sense to me if Benintendi or J.D. Martinez is dealt, and probably only if he isn’t extended the qualifying offer.