SSTN Mailbag: Rule 5, Winter Meeting Recap, And Chisholm Rumors!

As most of you know, I enjoy working on the opening monologue to the SSTN Mailbag almost as much as answering the questions that come in. This is the rare week where any monologue was something of a challenge, as I've been down for the count with pneumonia for a little over a week now (not to worry - I'm on the mend and should be doing...um, cartwheels, I guess...any day now). Apparently, breathing is a critical human function, but more troublesome for me has been the fatigue that goes along with it. For that reason, I had the energy to answer the questions that came into the Mailbag, but just didn't have enough juice to devote my usual energy to the monologue. Everything will be back to normal next week, as I'm already a closer to myself (my deepest apologies to those around me).

A quick housekeeping note before we get into the questions: I am incredibly grateful that people still send so many questions to the Mailbag years after we started doing this. Traditionally, in addition to answering questions that come directly into the email box for the Mailbag, I take questions that come through all sorts of other forums (comments section, write-in questions to the main blog, social media, etc.), and I will continue to do that to the best of my ability. However, as my time has become more restricted, it is difficult for me to track questions that don't come directly into the SSTN Mailbag. Please, keep the questions coming, and again, as I'm able, I'll grab questions from comments and other sources, but the most reliable way to have your questions answered is to send it in to the SSTN Mailbag inbox that I list in every Mailbag. Thanks for helping me to help you.

As always, thanks for the great questions and keep them coming to SSTNMailbag@gmail.com. In this week's SSTN Mailbag, we'll talk about the recent Rule 5 Draft, discuss the Winter Meetings, and evaluate the Jazz Chisholm trade rumors! Let's get at it:

Mike O. asks: I don't really expect anything, but I think it's cool that the Yankees picked someone in the rule 5 for the first time in forever. Who is Cade Winquest, and does he have any chance of sticking on the roster? What do you think about the fact that no Yankee farmhands got picked in the MLB portion of the draft?

I agree, I think it's a lot of fun that the Yankees made their first Rule 5 pick since 2011 (!). Being the baseball junkie that I am, I remembered that Ceasar Cabral was one of those two picks, but I had totally forgotten about Brad Meyers, who never made the Major Leagues. This is the fate of many Rule 5 picks, even more so in recent years, so there usually isn't a lot of fanfare for Rule 5 picks, outside of 2020-2021, when so many guys developed away from their home team's watching eyes.

Cade Winquest is very interesting to me, and while I wouldn't give him a better than 50/50 shot to stick, he's more interesting than one would assume from scouting just his minor league statistics. The last I heard of Winquest was when he pitched mostly in relief in the Cape Cod Baseball League (widely considered the best amateur summer league in the country). Winquest produced some very middling statistics in college, mostly as a starting pitcher, but performed quite well on the Cape out of the bullpen, which put him on the draft map for most teams. In fact, according to the Yankees' telling of their history with Winquest, they had planned to take him one round after Cam Schlittler in the 2022 MLB Draft, where Winquest was ultimately drafted by the Cardinals in the 8th round.

For the last two seasons, Winquest has started in the Cards' system, with mixed results. This past season, he reached AA, where his statistics started to turn a corner, posting an ERA under 3.20, though he remained too hittable for a pitcher who was essentially "5-and-dive." What makes Winquest interesting is his delivery, velocity, and a very good breaking ball.

Winquest gets great extension down the mound and hides the ball well. As a starter, he lives in the mid-high 90s with his fastball, touching 100 MPH. It's easy to imagine that Winquest could live in the high-90s and touch triple digits with far greater frequency as a 1-inning reliever who can let it eat. Winquest also has an excellent high-70s curveball that generates a ton of whiffs, and a useable slider and change-up. The pitch shapes Winquest produces are the types that the Yankee development staff, particularly Desi Drueschel, now that he's back in the fold, excel at fine-tuning. I argued throughout the last year-and-a-half that the Yankees needed more high-velocity arms in the bullpen, and this is an interesting low-cost lottery ticket that could achieve that aim. Again, having never pitched above AA, it will be a tough road for Winquest to stick, but the stuff is good enough that it wouldn't shock me that he can stick with some tweaks. I like the pick.

As far as eligible Yankee farmhands, I was surprised that no one took a flier on Brendan Beck or TJ Rumfield, and just mildly surprised that no one grabbed Brock Selvidge in an attempt to make him a lefty bullpen arm. Beck's loss of velocity at the end of last season likely tanked his value, while Rumfield is likely fully developed, but lacking the power teams typically expect of a big league 1B, while Selvidge just isn't ready. I think the fact that no Yankee farmhands were picked shows that the Yankees do a better job of evaluating their own talent than many give them credit for.

Brian S. asks: We saw a few high profile signings, but the Yankees did less than nothing this week. What should a fan think about this?

Yes, there were some high profile overpays, but otherwise, the Winter Meetings as a whole were a complete dud, with very few interesting rumors. Other than Scott Boras boosting his clients in his media time, we heard very little in the way of actionable rumors. In fact, Brian Cashman even complained to the media about just how behind other teams are in their offseason planning, where November was seemingly used for HR matters as opposed to roster planning. If we believe Cashman, he came to the Winter Meetings ready to deal, while others were just beginning to sort through their options. Besides that, it's obvious that the Yankees have made Bellinger their prime target, and we know that Boras is going to drag that negotiation out a bit, at least until Tucker signs.

This was not how I expected the offseason to roll; I thought players would be jumping to secure their futures with the labor uncertainty that looms in the background. I was completely wrong on that one, and I think teams are playing the long game.

That said, I really, really hope that zeroing in on Bellinger doesn't preclude Cashman from attacking opportunities elsewhere. I am very surprised that we haven't even heard rumors about the big Japanese imports coming stateside, though I expect the Yankees to be in on Imai. As a Yankee fan, I'm frustrated that we got a giant nothing-burger out of this week, but at least we're not the Mets.

Andrew H. asks: What do you make of all of the rumors about the Yankees trading Jazz Chisholm?

I think this more a situation where the Yankees will listen on basically anyone who isn't Aaron Judge, though that is different than saying that everyone is available. I expect that the Yankees would place an extremely high price tag on Jazz Chisholm, as they should. I've heard some grumbling about him from the Yankee faithful, and frankly, I don't understand it at all.

I know that Chisholm's personality grates at some of the old school fans, but as someone who straddles the line between old and new school, I love him. Regardless of how you feel about his style, it's hard to argue with his ability. He has speed, power, defense, and runs the bases incredibly well. Yes, he's streaky; yes, he probably over-swings too frequently; and yes, he's probably a bit over-aggressive sometimes. To get lost in those flaws is to lose the forest through the trees. Chisholm brings tons of energy to the lineup and his aggregate performance makes him one of the 3-5 best 2B in the sport. To get rid of Chisholm means that there needs to be significant big league pieces coming back that can produce similar value at multiple spots. I'm not saying that's impossible, but few teams would part with a package that makes sense for Chisholm.

I would argue that the Yankees should be looking at an extension for Chisholm as opposed to a trade. I see a trade as unlikely given the current market conditions, so I think working out an extension that works for both sides makes a lot more sense prior to the expiring CBA.