10 thoughts: Ben Cherington has one tough trade down, at least one to go – DKPittsburghSports.com

MILWAUKEE — Ben Cherington‘s first deal of the trade deadline came Friday morning, sending Jarrod Dyson to the White Sox for international bonus pool money.

Speaking of pools, who had Dyson as the first to be traded? I’ll admit I didn’t. Not with how his season has gone to this point.

In the grand scheme of things, that extra $243,300 in spending room that Dyson brought back isn’t much, especially in this stage of the signing process. COVID-19 pushed the start of the next signing period to Jan. 15, 2021. In a normal year, everyone still available would have either been officially passed on or signed the following year for significantly less.

So, in essence, the Pirates acquired the right to buy up to $243,300 worth of the leftovers, something that the White Sox weren’t that keen on doing. But it’s something, and getting anything for a -0.7 WAR player is pretty good.

It couldn’t have been easy to find a buyer. Cherington has another one of those tough deals still to make in Keone Kela.

Kela was placed on the 10-day injured list Thursday with right forearm inflammation. That’s on top of him missing all of summer camp and a big chunk of the regular season with COVID-19.

All told, he’s pitched two innings this season, and there’s no guarantee for when he could return. Again, it’s a tough sell.

The market for rental pitchers seems thin right now. Taijuan Walker fetched a player to be named later, meaning someone outside of the 60-player pool. Brandon Workman had to be packaged with Heath Hembree, who has an additional year of control, to get a fringe prospect and a starter who has done nothing but struggle in the majors from the Phillies. So even if Kela was cruising, the return probably would have been small.

But Cherington is in a position where he needs to make this deal. Kela is gone at the end of the year, and the Pirates really aren’t in a position to try to resign him. A fringe prospect or lottery ticket is better than nothing. Finding someone willing to give that up for a handful of regular season and playoff innings wasn’t going to be easy, even before the injury.

• With Dyson gone, Cole Tucker seems next in line to get the majority of the playing time in center field.

The Pirates have insisted that he will be going back to the infield, but what if this is his new permanent home?

With the way the roster in constructed, there’s a good chance the Pirates would need to find another fill-in center fielder like Dyson for 2021, unless it’s Tucker, Jason Martin or Jared Oliva (more on him in a minute). Gregory Polanco doesn’t look like a part of their long-term plans, either.

The team has plenty of young middle infielders, including Kevin Newman, Nick Gonzales, Oneil Cruz and Liover Pegeuro, but not a lot of outfielders. Moving Tucker to the outfield was out of necessity, but he has performed well and has improved at the dish with more consistent playing time. Why fight something that appears to be working?

• While Martin is taking Dyson’s roster spot for now, Anthony Alford should get a call before too long. He was a top-three prospect in the Blue Jays’ system from 2016-2018, which were Cherington’s first seasons with the organization.

He still has the raw power and speed that made scouts fall in love with him, but it hasn’t translated well in the majors or class AAA. It looks like he’s straightened out his stance this year, rather than being in what looked like an awkward crouch from before. Perhaps that will help him see the ball better.

Even if it doesn’t, Alford ranks in the top 1% of baseball players in sprint speed, per Baseball Savant, so the worst case scenario is the Pirates traded an older, speedy outfielder for a younger one. Considering where they are in a potential rebuild, that’s a zero-risk move.

• Oliva is another guy who it would be nice to see get some reps in the outfield this season. I’ve heard nothing but rave reviews from him out of the Altoona training site, and the Pirates included him on the taxi squad for their Cincinnati road series as a reward for the work he had done.

He should, at the very least be, in the outfield mix in 2021. Ideally, he’s the prototypical leadoff man: Someone who can work pitchers, get on base and steal some bags. He stole a combined 69 bases compared to 18 caught stealings in 2018 and 2019, good for a nearly 80% success rate.

Picking up Alford does decrease his chances of being on the roster this year, but he will need to be added to the 40-man this offseason anyway. There are only five outfielders on the roster right now, and with the end of the season only a month away, it could take just one minor injury for him to get a call.

• Going back to the trade deadline, with the sheer number of pitcher injuries across baseball, someone like Derek Holland is a perfect buy-low option for clubs who need depth. He could slide into the backend of a rotation or provide left-handed relief, if not transition from the former role to the later during the postseason.

Each team will value an inning eater differently, depending on how badly they need help. In any case, it seems doubtful Holland would bring back anything more than a fringe prospect. At that point, if the Pirates trade away someone else from the rotation, it might be worth hanging on to him for the rest of the year, just to take some pressure off of the rest of the staff.

Chad Kuhl arguably has the best pure stuff in the rotation, and unlike the previous leadership regime, pitching coach Oscar Marin knows how to better utilize it. In case you haven’t been keeping up, he now has a 2.52 ERA and 1.08 WHIP this season.

There’s a reason why the Blue Jays would be interested in him. One of the best comps for his pitch velocity, spin and movement is Gerrit Cole. Not to say that Kuhl will be as good as Cole, but he’s having much more success this year following the playbook Cole did when he went to the Astros. It’s translating again.

The Astros bought Cole low partially because he was a bit of a fixer-upper. The Pirates didn’t know how to do it then. They do now with Kuhl. So if teams are hoping to get Kuhl, they need to pay like they’re getting a No. 2 or 3 starter, not the 4 or 5 guy he was earlier in his career. At this point, his value is only going up, and he is the type of guy the club might be better off hanging on to for the time being.

Trevor Williams‘ most recent outing is barely going to impact his trade value, if at all. He’s shown this year that the fastball plays like it did in the past, and that the changeup and curveball are good backup options outside of his fastball-slider combo. A couple of home runs that barely left the yard isn’t going to sour executives.

To eyeball a potential deal with the Blue Jays, who need controllable starters, even after the Walker deal, someone like right-handed pitcher Alek Manoah seems to be a good return. Monoah is just outside of the top 100 prospects, mostly because he has some command issues and is still developing a third pitch.

Assistant general manager Steve Sanders took a risk to draft him last year with the Blue Jays, even though he wasn’t a three year starter in college. The reward is high, but it seems like he could slide into the bullpen worst case scenario, as the slider and fastball both play.

Richard Rodriguez is on a perfect contract for this deadline. He has pitched very well in a variety of roles, has three years of arbitration control remaining and barely costs anything for cash-strapped teams in 2020. Don’t expect a top-100 prospect for him, but someone from a team’s top 10 is more than reasonable, probably about fifth or sixth.

• It’s pretty telling that there has barely even been a whisper about Josh Bell or Adam Frazier this trade deadline. I seriously doubt either is dealt this week.

• In a perfect world, the Pirates would find their catcher of the future this trade deadline and move him to the Altoona camp so he can get some formal instruction, but the Pirates aren’t in a position to make a trade for a certain type of player. They need to get as much talent as possible.

If you trade away major-league talent based on need, you get trades like the Cole deal.

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