Ben Cherington’s Winter Meeting History – Look at all these rumors….

12-2-23 – By Justin Verno – @JV_Pitt on X

When Corey Shrader, Joe Boyd and myself set out on this year’s Winter Meeting trade pieces journey, we had hoped to finish it up with a bang.

At long last, the Bucs would be adding some pieces and not sending some guys packing. We finally got to sink our teeth into giving up some kids to fill holes on a team ready to set sail.  How fun, we thought. 

Hell, even General Manager Ben Cherington hinted at moves.  Going as far as hinting at specific areas he needed to address. As seen here, courtesy of Jason Mackey.

Between that report and some other quotes….

“a different type of target” 

We’ve been mostly focused on starting pitching, both in free agency and trade

Here’s a cut out from MLBTR.com

In terms of moves to improve the roster in 2024, the GM spoke about potential trades and free agent acquisitions. In terms of trades, Cherington said he isn’t taking anything off the table right now, and he’d be willing to make a significant trade if he saw it as the best way to upgrade the roster. As for free agents, he didn’t rule out the possibility of some signings, but he cautioned that he doesn’t want to “lean on free agency exclusively” as a means of improving the club. 

Yes, finally at long last we’d have a big fat juicy steak to cut into come the Winter Meetings. 

The rumors, we thought, would be rolling in faster than we could say “Raise the Jolly Roger.”

We waited.

And waited.

And we waited.

Nothing. Nada. Zip. Zilch. Zero. Not one chunk of coal in our stockings. 

Want to hear something more depressing? Here’s a quick list of every Ben Cherington Winter meeting trade I could wrangle up.

As GM of the Boston Red Sox-

2012 December Winter Meetings

None. 

2013 December Winter Meetings

None.

2014 December Winter Meetings 

11th, Dec-Acquired RHP Rick Porcello for OF Yoenis Cespedes, RHP Alex Wilson and LHP Greg Speier

(side note, Cespedes had been a July Trade Deadline deal that year  for GMBC)

December 12th of ‘14 he would make another deal. Clearly the ground work would have been done at the Winter Meetings, as many deals that eventually get done are. 

LHP Wade Miley for  Rubby De La Rosa, RHP Allan Webster and INF Raymal Flores. 

I would certainly call the Rick Porcello trade a success. 

As GM of the Pittsburgh Pirates-

2019 December Winter Meetings

None.

2020 December Winter Meetings

None.

2021 December Winter Meetings

None.

2022 December Winter Meetings

None.

By no means am I trying to send up the alarms. I’m not shouting to abandon ship. As I mentioned above, when GMs finally pull the trigger on a trade in the off-season, much of the ground work was done during the Winter Meetings. 

But talk about a killjoy. Am I right? This is like Santa finally sliding down your chimney in late February with the GI Joes already open and half the legos from your X-Wing Starfighter kit missing. Sure, you got to open the damn thing but that excitement? Yeah, that went away when the snow melted and the leaves started to bud.

Is this to say it’s “joever”? (that’s what the kids are saying these days? Right?)

Well, if we can gleam one quick positive here. In 2014 when GMBC thought Boston was ready he did add Rick Porcello and Wade Miley, so we got that going for us. Which is nice. 

How fun indeed.

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