Is this the year the Phillies can sidestep their flaws and return to the postseason? Buying at the deadline would help, but as badly as everyone wants them to, the risks may not outweigh the rewards. (AP Photo/Chris Szagola)

The Phillies currently have the second-longest active postseason drought in baseball and the longest in the NL, and this fact has been ingrained in the minds of fans over the last three seasons. Each has come both so close and yet so far from ending the latest dismal stretch in a franchise known for them. Management has operated with this drought in mind, of course, but the dry spell seems to be bugging them now more than ever.

Each of the last three years, the Phillies have bought in bulk at the trade deadline, but few of the players they have acquired have provided significant value. 2018? Wilson Ramos was fun for about a week. Asdrúbal Cabrera had an exciting walk-off home-run once. But acquiring both threw off the clubhouse chemistry and pushed out the young talent that defined that team. 2019? Corey Dickerson was decent but, through little to no fault of his own, failed to move the needle. Every other addition was extremely forgettable at best. As for last year, you could make the argument the biggest reason the Phillies missed the Postseason in 2020 was the trade that brought Brandon Workman and Heath Hembree to Philadelphia. They combined for -0.9 WAR in their month or so as Phillies.

Dave Dombrowski has bought at almost every single trade deadline of his career when his team is within sniffing range of the postseason. A weak NL East is the only reason the Phillies fit that profile, as they are eight games behind the Padres for the second wild-card spot and would be buried in any division except their current one. Dombrowski’s track record of buying and winning is what brought him to Philadelphia. It kept the Phillies from shedding massive amounts of payroll in the offseason and it may result in the team crossing the luxury tax for the first time since it was added in 1997.

The Phillies have been hesitant to cross the threshold not just because of the financial penalty for doing so, but because of uncertainty that doing so would actually benefit the club. Owner John Middleton stated he would not surpass the tax just for a better shot at being the second Wild Card team but technically, the Phillies have a better shot at winning their division than securing a Wild Card slot. Regardless, their odds of winning a postseason series would likely be slimmer than either of the NL’s Wild Card teams, even when accounting for the slightly easier path the Phillies would face as a division winner.

If the Phillies buy, their needs are obvious: pitching, pitching, and more pitching. Maybe center field, too, but that seems to be less of a priority. Zach Eflin’s injury throws a massive wrench in the plans. Every team’s top three starting pitchers are important, but the Phillies have relied on theirs more than most. Both Eflin and the team expressed optimism regarding his status for the rest of the season, but any long-term injury would make buying a poor decision.

Assuming Eflin’s injury doesn’t make the decision for Philly, Dombrowski sounds adamant about acquiring at least one or two pitchers to help his club’s postseason pursuit. John Heyman reported the Phillies are interested in Cubs closer Craig Kimbrel, a former acquisition of Dombrowski’s when he was the GM in Boston. Kimbrel would give the Phillies their first proven non-Héctor Neris closer since Jonathan Papelbon. The Cubs have two other relievers in Ryan Tepera and Andrew Chafin (a lefty) who could also fit. Staying in the NL Central, Pittsburgh closer Richard Rodriguez would provide the same ninth inning stability as Kimbrel. Twins lefty Taylor Rodgers is in the same story.

If the demand is too high for Philadelphia’s depleted farm system to match, more reasonable options like Texas’ Ian Kennedy or Washington’s Daniel Hudson could be available. Making a run at one of the top starters on the block like the Rangers’ Kyle Gibson or Colorado’s Jon Gray seems very unlikely, but no pitching addition is too big for the 2021 Phillies.

The problem with buying is that the Phillies bullpen is so flawed that adding one or even two relievers seems unlikely to have a dramatic impact. That being said, the potential trickle-down effect is intriguing. Lefties Ranger Suarez and Bailey Falter have been surprisingly solid in late-inning roles, with Suarez recently becoming closer. Acquiring another reliever could decrease their responsibilities and improve balance, or it could allow a reverse 2007 Brett Myers move from the bullpen to the rotation, where both players began the year in the Minors.

Considering how bad Vince Velasquez has been against non-Marlins opponents and how bad Matt Moore has been against, well, everyone, it is an intriguing proposition. But again, even if that happens and Eflin returns in soon, one would still remain in the rotation. It is not a matter of figuring out how to plug all of the holes; rather, predicting the damage that will come from leaving each unfilled and acting accordingly.

After a second straight month where a strong start (four straight series wins) has been followed by another step back (a 3-4 week with embarrassing defeats abound), the merits of buying should be called into question. Even if the Phillies can fix their pitching woes to a reasonable extent, it may not be enough. The defense will still remain below average and the offense may not get back to its pre-All-Star break July form. Maybe COVID-19 will break the Phillies’ back this time around. The Phillies are a team that can lose in many different ways, and an active deadline approach only solves one, maybe two of them. The others will need to be addressed by largely the same group that has failed to do so for three straight seasons.

If the Phillies want to maximize their chances of reaching the postseason this year or next, selling seems to be the best option. Trading a combination of Andrew McCutchen, Archie Bradley, Brad Miller, and other soon-to-be free agents would help restock the prospect cupboard. The prospects that players like those would bring in could be reinvested in more practical and/or long-term solutions in the next twelve months, or they could stay to help out the Phillies further in the future.

But it is hard to justify selling with 28-year old Bryce Harper, 30-year old J.T. Realmuto, and 31-year old Zack Wheeler combining for about $72 million against the luxury tax. You only get so many chances with players at such a high level of play. Selling this week to invest in 2022 sounds smart, but what if 2022 is not worth an investment at all? Then again, having a second chance to invest the $11 million tied up in Moore, Chase Anderson, Matt Joyce, and Brandon Kintzler could make buying worthwhile; maybe even a luxury. This is the debate Dave Dombrowski and his staff will be having for the next five days.

The Phillies know some of the things they are and are not willing to do before the July 30 trade deadline. They are willing to acquire rentals if the price is right. They are not willing to part with Bryson Stott, Mick Abel, or Andrew Painter, their three most recent first-round picks. Perhaps most importantly, they are able to exceed the luxury tax if need be. Management wants to buy because ownership has finally given their blessing, and the excitement surrounding that choice is understandable, but the defensive gaffs and pitching meltdowns still provide some understandable reasons to be cautious.

The Phillies’ overall level of play really does not warrant buying, but between a potential lockout this offseason and the NL East Standings, there are outside factors making buying a more attractive option. Only a massive collapse over the next week feels like it would prevent Dombrowski from pulling the trigger on at least one meaningful trade. Could such a stretch be good in the long run? Perhaps, but the organization knows that even if that is the case, some fans may not be willing to see in through. Attendance and morale are low, and the cost to buy will likely be high.

PLEASE let this age poorly. For all of Philadelphia’s sake.

The Phillies can not afford to buy and be actively wrong for the fourth straight year. Each of the last three years, the Phillies have been like a greedy child at the mall in December. They know what they want Santa to bring them but have an imperfect idea of how to convince him to provide it. Their approach must be different this year, even if it looks similar on the outside. When the lights turn off following baseball’s Christmas in July, the Phillies organization must be in a better place, plain and simple.

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