Perrotto: How Will Ben Cherington Approach Trade Deadline?

There is only one way the Pittsburgh Pirates should approach the trade deadline next month.

With a 29-45 record, the Pirates are already 16 games behind the National League Central-leading Chicago Cubs. The Pirates are also 11.5 games out in the race for the third and final NL wild card.

The Pirates have about as much chance of making the playoffs this season as I do of walking on the moon. It just isn’t going to happen, regardless of them playing much more respectably since bench coach Don Kelly was promoted to replace manager Derek Shelton on May 9.

Disturbingly, the Pirates don’t look any more like a contending team than when general manager Ben Cherington replaced Neal Huntington after the 2019 season. The Pirates can’t score runs, and there aren’t any quick fixes for the offense in the farm system.

The Pirates need to shake things up between now and July 31. They need to go into rebuild mode yet again because this rebuild hasn’t gotten off the ground after more than five seasons.

However, it is not so clear that the Pirates will be big-time sellers at the deadline. Cherington’s tenuous job status clouds the situation.

The general sentiment among the Pirates is that a strong finish to the season is necessary for Cherington to be considered for a return in 2026.

Yet it would be difficult to imagine the Pirates having a strong finish if they traded too many of their veterans. It wouldn’t be self-preserving for Cherington to make a lot of deals for prospects and watch the Pirates potentially finish with 100 losses for the third time in his tenure.

So that leaves Cherington facing a difficult decision on how to handle the deadline.

If he trades too many veterans, the Pirates will struggle over the final two months of the season, therefore lessening Cherington’s chances of keeping his job. Yet if the Pirates don’t start another rebuild, or at least a significant retool, then the franchise will continue to be stuck in baseball purgatory with little hope of contending anytime soon.

Does Cherington do what’s best for him or the franchise? Tough call.

The Pirates told teams that they are willing to listen to trade proposals for any players except right-hander Paul Skenes and center fielder Oneil Cruz.

A case can be made that the Pirates should consider offers for both players, even though they are franchise cornerstones. Skenes and Cruz could generate the type of return that would infuse more high-end young talent, something the Pirates need.

Trading either player, though, would likely be career suicide for Cherington. It’s difficult to imagine owner Bob Nutting signing off on dealing key players with low salaries.

And would Cherington consider dumping the contracts of right-hander Mitch Keller, third baseman Ke’Bryan Hayes, and right fielder Bryan Reynolds? Cherington struck each of those three deals, and he’d have to swallow hard to admit that none of them are turning out the way the Pirates hoped.

The Pirates have other tradeable commodities — left-handed starters Bailey Falter and Andrew Heaney, lefty reliever Caleb Ferguson, right-handed bullpen arms David Bednar and Dennis Santan,a and shortstop Isiah Kiner-Falefa.

It is doubtful that Cherington can make a blockbuster trade with any of those players. However, he should be able to get something decent in return for them.

The Pirates need to overhaul their roster. The question is whether a perceived lame-duck GM can do it.