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The 3 teams with the hardest decisions to make at the MLB trade deadline

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Buy? Sell? Something in between? There are dozens of ways these three teams can succeed or fail at the trade deadline, so good luck telling them what to do.

I can't tell if Monday night's game helped or hurt the thesis of this article, tbh.
I can't tell if Monday night's game helped or hurt the thesis of this article, tbh.
Joe Nicholson-USA TODAY Sports

The Yankees were supposed to have the hardest decision to make at the trade deadline. At least, that’s what it looked like in May. All signs, though, are pointing to the Yankees selling, at least when it comes to their pending free agents, like Carlos Beltran and Aroldis Chapman. Their most interesting decision will probably have to do with keeping Andrew Miller, who is under contract for long enough to help the next great Yankees team, in theory.

There are other teams at the crossroads, though. This is an annual occurrence, in no small part because of the expanded wild card and postseason, but it’s not just a wild card phenomenon. Last season, the Blue Jays were .500 on July 18. The Rangers were 43-48 — not too dissimilar from the 2016 Phillies, really. Both the Blue Jays and Rangers stormed back to win their respective divisions.

Guess what? There will be a contender that you’ve already filed away as an also-ran. At least one team will climb out of the tar pits. At least one team should trade for the Troy Tulowitzki or Cole Hamels of 2016 and come with them if they want to live. This team should trade prospects, all of the prospects, to support this newly urgent win-now mode. Their success will rally the fans, and the excitement will spill over into the following season.

I’ve done my job. Your job is to pick the team that will actually do it, being careful not to ruin the futures of the five or six teams that won’t make a miracle surge. So good luck with that. And be careful, this stuff can mess an organization up for a decade.

These are the teams with the hardest decisions to make at the trade deadline, which is ...  in 13 days?

wait how in the hell are we at the deadline already

Seattle Mariners

My pick to win the pennant! DON’T LOOK AT THE OTHER PREDICTIONS. Actually, don’t look at that one, either. Forget this entire article exists, really. Here’s a video of a cat in a shark costume on a Roomba chasing a duckling. Do something productive with your life.

The Mariners are a game over .500, and they’re within spitting distance of the wild card. They’re within ... javelin distance of the division, which isn’t impossible to overcome. But it’s probably best to focus on the wild card and hope more tumblers click into place. The easiest way to do that is to keep the team together and hope for a surge. It’s an uncontroversial strategy, at least.

It doesn’t help that it’s tough to see exactly how the Mariners get better in this trade market. A trade for Josh Reddick would push Nelson Cruz back into the DH role he was born for, with Adam Lind and his .262 on-base percentage losing the bulk of the playing time, but that’s the kind of move a team makes when they’re either leading the division or right behind the leader. This doesn’t have the feel of a team that’s only a rental away from gaining five games on the wild card leaders.

To put their choices in 2015 terms, they can be the Blue Jays (go wild, deal all of the prospects), the Yankees (do nothing, prepare for the next season), or the Tigers (cash the season in for prospects). Being this season’s Blue Jays sounds great! Except it’s a dangerous game to expect that kind of reversal, and it ignores just how historically improbable the 2015 Blue Jays were.

The lesson of the ‘15 Blue Jays and Rangers, then, is to consider the big whopper deals, but make sure that the players are around to help next year. If that means exchanging prospects and flexibility for Julio Teheran and Nick Markakis, go for it. Don’t think of it as a win-now attitude. Think of it as a win-at-some-point-dang-it method to combat frustration.

Chicago White Sox

The White Sox are, quite possibly, a lousy team. Chris Sale and Jose Quintana should start Games 1 and 2 of a World Series in a perfect world, but like the old tautology goes, "When Melky Cabrera is the best hitter on the team, Melky Cabrera is the best hitter on your team." The fast start from Adam Eaton has faded. Todd Frazier is back to his old self, ostensibly, which is a great way to remind everyone that he was only pretty good in the first place. Jose Abreu just might be special again, but that’s not going to carry a lineup. Even considering the upward trend of his last four starts, James Shields isn’t missing bats, and that’s going to be a problem at U.S. Cellular.

According to expected record, the White Sox should be 43-49. Back to that first sentence, then. The White Sox are, quite possibly, a lousy team.

Like I argued before the season, though, it would be silly for the White Sox to demolish the house and start building on the vacant lot. They have Sale and Quintana, which is an otherworldly start to any roster. Trading them for seven prospects who each have about a eight-percent chance of turning into the next Sale and Quintana is like cashing out a 401(k) for a Vegas trip. You might come back with more money! It’s probably smarter to leave it alone and figure out other get-rich-quick schemes, though.

The compromise, then, is to half-rebuild, using the bullpen as trade chips in a bullpen-thin market. I’m not sure if anyone would bite on David Robertson’s contract after his disappointing season, but even with his very, very, very memorable blow-ups, he’s allowed a run in just seven of his 36 appearances. He’s allowed more than one run in just three of them. A team could bite.

We know teams would go for Nate Jones and Zach Duke, though. And while it’s not like the White Sox can guarantee there will be more relievers on the reliever tree this offseason, it’s easier to reload and build a bullpen on the fly than it is to find a new top of the rotation and start all over.

From here, though, just based on the Shields acquisition, it looks like they might be going for it. Again, the Rangers from last year make it hard to issue definitive proclamations about the wisdom of that strategy, but it’s worth remembering that the White Sox are, quite possibly, a lousy team. Splitting the difference makes much more sense for them.

Pittsburgh Pirates

The anti-White Sox, in that I’m pretty sure that the Pirates are, quite possibly, a pretty good team. They just flew too close to the sun on wings made of Ray Searage, and they’re scrambling now. It turns out that an offseason filled with Jon Niese and Ryan Vogelsong is a medium-to-high-risk, low-reward offseason, and if the Pirates thought it was hard to build a rotation without spending last offseason, they’ll find it’s really hard to build a rotation without spending going forward.

The good news is that they’re easing Jameson Taillon and Tyler Glasnow into the picture, giving them a potential big three that could be around for years. Other than David Freese, all of the particulars are young and will be around for a couple of years, at least. They probably have the best argument for a Blue Jays-like splash, going for it against the odds, if only because they’re confident about the true talent level of the 25- and 40-man rosters.

The problem with that is that if the Blue Jays didn’t have much of a margin for error, the Pirates really don’t have a margin for error. They can’t absorb a Tulowitzki-sized contract and laugh it off if it doesn’t work. This is still a low-payroll team in the smallest of markets, and their recent history of success can’t change that.

In another season, with another set of buyers and sellers, I’d suggest the Pirates should target low-cost rentals, then. Give up prospects that might sting later, but keep the financial flexibility intact. They are likely to contend next year, even without doing much of anything in the offseason, so patch this team and look forward to 2017 if it doesn’t work out.

There are no low-cost rentals in this market, though. Every half-decent player will cost the prospect equivalent of a million-billion dollars. The Pirates can’t mess with that, so unless they’re capable of and willing to swing a Drew Pomeranz-type deal for an under-contract pitcher, they should probably take advantage of the upside-down market and consider dealing Mark Melancon, Tony Watson, and Neftali Feliz. The former is almost a given, considering he’s a free agent.

It wouldn’t be a white flag of a deal. It would be an acknowledgement that any success the Pirates will enjoy over the next decade will be predicated on them acquiring and developing young talent. There might never be an organization that will have less business giving away young talent for a low-odds wild card shot.

What do all three teams have in common? They shouldn’t hold an estate sale. They might just want to put a couple items on Craigslist. The Mariners should be somewhat aggressive, the White Sox should avoid a dramatic overhaul, and the Pirates should keep an eye on the 2017 season, no matter what they do. And yet all three teams should at least consider dumping any pending free agents or overvalued relievers.

These are the teams with the hardest decisions to make at the deadline. It looks so easy from here, but the Blue Jays and Rangers reminded us last year that baseball exists only to make people with keyboards look stupid, always and forever. One of these teams will be relevant in the last week of the season. Your job is to figure out which one and mortgage the future accordingly.

Good luck.