Is Dave Dombrowski really prone to overpaying in trades?

We are now less than two weeks from the trade deadline, which means we are smack dab in the middle of the most exciting part of the season. Rumors are coming out left and right, and everyone has their opinion on what their team should be. The Red Sox are expected to be relatively busy this year, perhaps making multiple trades. However, they also aren’t expected to deal for any true stars, instead looking at mid-tier solutions. Despite that, Red Sox fans everywhere are antsy for what Dave Dombrowski will do, because people are terrified that he will overpay for whoever he wants. That is his reputation as a front office executive, and it’s nearly impossible to change these kind of opinions. Is it a deserved reputation, though? To figure it out, let’s look through his major trades since coming to Boston and see if they were really overpays, both at the time and in hindsight.

Craig Kimbrel

In one of Dombrowski’s first big moves as the head of the Red Sox front office, he got one of the most well-regarded closers in baseball for a package of Manuel Margot, Javier Guerra, Carlos Asuaje and Logan Allen. At the time, it was expected the Red Sox were going to look at a big closer, and someone like Kimbrel who had multiple years of control was always going to cost a lot of money. On the one hand, this was before the shift around the league where the value of elite relievers has seemingly gone up. This seemed like a lot to pay for a reliever at the time, in hindsight it is a fair package. It’s hard to say whether Dombrowski just anticipated the change in the market or if he sparked it. To me, it’s a slight overpay, but not one that you can’t live with. Margot was hard to part with, but at the time there was a split between him and Andrew Benintendi, and the Red Sox kept the right one. The issue was that it seemed as if they could have done it without both of Asuaje and Allen. Those aren’t the type of prospects that should kill a deal, of course, but it would’ve been better if one of those two were still with the organization. Still, if this is an overpay it’s not one by a drastic extent at all.

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Carson Smith

This is actually one of the more underrated trades of the Dombrowski era despite not getting anything in return just yet. Shortly before the Kimbrel deal, the Red Sox sent Wade Miley and Jonathan Aro to Seattle for Carson Smith and Roenis Elias. When this deal happened, I literally said there’s no way the Red Sox are getting Smith back in this deal, so don’t get excited. They got Smith about two minutes later. Now, the reliever hasn’t pitched yet for the Red Sox (well, he’s thrown 2 ²⁄₃ innings but that doesn’t count), but Miley has ranged from average to bad — and he’s been bad much more often — since leaving and Aro hasn’t done anything. I’m still confident this was a good trade for Dombrowski, even if it’s turned out to be much more risky than we thought.

Brad Ziegler

Along those same lines, this is likely the best trade Dombrowski has made with the Red Sox in terms of straight-up value. To get Brad Ziegler from the Diamondbacks he only had to send Luis Alejandro Basabe. The common explanation is that the Diamondbacks accidentally asked for the wrong Basabe brother, and I 100 percent believe that to be the case. Either way, this was an absolute heist getting a very talented reliever who could be trusted down the stretch in high-leverage situations for a fringe prospect. This is easily not an overpay.

Drew Pomeranz

Here, we have one of the more controversial trades of the Dombrowski era, or really any recent era of Red Sox baseball. At the time of the trade, I found it fascinating but my initial reaction was that sending Anderson Espinoza for Drew Pomeranz was a bit of an overpay. I understood the merits, as the Red Sox were getting a talented pitcher who was under control for multiple seasons. Now, Pomeranz was in the midst of his one good season, so there was risk this was a fluke. That said, there were tangible reasons for his breakout and reason to believe it could continue. In the end, this was a fascinating trade where Dombrowski traded one talented but risky prospect for one player rather than a package. It seemed like a slight overpay at the time, but the executive has been redeemed to some extent this year. We won’t know how this trade truly turned out for a few years, at least.

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Chris Sale

Here is the ultimate Dombrowski deal. There’s no doubt he gave up a ton in this deal, sending Yoan Moncada, Michael Kopech, Luis Alexander Basabe and Victor Diaz. Moncada, of course, is arguably the top prospect in all of baseball and has an absurdly high ceiling. Kopech is one of the more exciting pitching prospects in the game. Basabe is still raw, but he has an underrated ceiling if everything clicks. With all of that being said, the Red Sox got one of the best pitchers in the entire league on one of the most team-friendly deals around. They were always going to have to give up a lot for Sale, and if anything this seemed a little light at the time of the trade. If you recall, when these rumors started popping up last summer the White Sox reportedly wanted both Moncada and Benintendi. Just sending Moncada with some talented but high-risk (many still see Kopech as a future reliever) prospects was a win for Dombrowski.

Tyler Thornburg

So, uh, yeah. This is the one that is hard to defend. To get Thornburg, the Red Sox sent Travis Shaw, Mauricio Dubon and Josh Pennington to the Brewers. Since then, they’ve also shipped Yeison Cocoa to Milwaukee as a player to be named later. At the time, I understood where they were coming from but it still seemed like too much for me. To be fair, I am also higher on Dubon than literally anyone else on Earth. Still, this was a shaky deal at the time and it’s only gotten infinitely worse since then. If you are one to bash Dombrowski, this is the trade on which to hang your hat.

Examining the possibility of the Red Sox trading for a catcher

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Should they be targeting players behind the plate?

In the end, I don’t think Dombrowski has earned his “overpaying” reputation, at least not since he’s joined the Red Sox. It’s true that he’s sent some major prospects to other organizations, but he’s usually gotten elite talent in return. You could argue that Pomeranz isn’t an elite talent (he isn’t) but he’s still very good, doesn’t cost the team much money and is under control for multiple seasons. That is a valuable player for an organization. The other thing I would point out based on his entire career — not just his time with Boston — is that he has generally done a good job of trading prospects that don’t pan out. There’s no reason to blindly trust every deal Dombrowski makes — where’s the fun in that? — but don’t freak out about what he’ll do this summer. Generally speaking, he knows what he’s doing. Just....just don’t do the Thornburg thing again.