Matt Klentak has been the general manager of the Philadelphia Phillies for nearly two years. He was hired in late October of 2015, and has been at the helm for the last year and a half of the Phils’ long rebuild back to contention.

He inherited a team that had a lot of problems, but started off his tenure aggressively, surprising everyone by trading young closer Ken Giles to the Houston Astros for Vince Velasquez, Tom Eshelman, Brett Oberholtzer and Mark Appel. (Actually, the initial move was reported to involve outfield prospect Derek Fisher and not Appel, but the two were reportedly swapped out over concerns regarding Velasquez’ medical history).

It was a bold stroke by the new GM and seemed to indicate he would not be shy in moving on from core members of the team if the right deal came along.

Since then, he’s mostly fiddled around the edges, adding veterans on one-year deals to act as bridges to the many prospects on the farm. Some of those deals have worked, others have not.

The Phillies have gotten a decent season and a half of Jeremy Hellickson, a valuable thing even if they haven’t been able to trade him like they originally planned. Charlie Morton and Clay Buchholz were injury busts. Michael Saunders was simply awful, while Howie Kendrick has been good when not on the disabled list and Pat Neshek has turned in an All-Star performance this year. Other vets like Joaquin Benoit and Peter Bourjos provided mixed results.

Klentak has approached the last two off-seasons with the approach of a doctor - “Do no harm.” And no, the Phillies haven’t been tanking these last two years, they’ve been trying to maintain roster flexibility so that, when guys like Nick Williams, Aaron Altherr, Dylan Cozens, Roman Quinn, J.P. Crawford, Rhys Hoskins, Scott Kingery and others were/are ready to go, they can join the big club with little hassle.

However, with the trade deadline upon us and youngsters like Hoskins, Kingery and potentially Crawford knocking on the big league door, it’s time for Klentak to make some decisions. None of them are easy.

At first base, he has to figure out what to do with Tommy Joseph. A trade for the young first baseman would be ideal, as everyone in the organization recognizes Hoskins is ready for a promotion and probably has the higher ceiling of the two. But there is a glut of potential first basemen on the market, including Miami’s Justin Bour, Oakland’s Yonder Alonso, Toronto’s Justin Smoak, and Atlanta’s Matt Adams, among others. There may not be enough teams with a need at 1B/DH to accommodate Joseph.

What happens on August 1 if Joseph isn’t traded? Does the status quo remain? Does Joseph get demoted? Released? Benched? Does Hoskins simply stay in Lehigh Valley all year and the issue gets punted to 2018?

Decisions at second base and shortstop are more likely to be made this winter. If Cesar Hernandez comes back from his oblique injury and plays well, Klentak will have to decide if Hernandez is his second baseman of the future, or if it is going to be Kingery. And whatever he decides, a trade of the other is most likely necessary, unless they feel Kingery or Hernandez can move across the diamond and play third base.

Of course, if the Phillies move one or the other to third, what happens with Maikel Franco? Still just 24, his season has been a struggle, with a -0.5 fWAR this season that is tied for 158th out of 166 qualified MLB players. Nick Cafardo of the Boston Globe recently reported the Phils were willing to listen to offers for him. It’s likely they’d have to be overwhelmed to deal him, but what if moving Franco is the only way to keep Hernandez and Kingery?

And then there is the shortstop position. Freddy Galvis has stepped up and taken a true leadership role on this team. He also provides Gold Glove defense and ample pop for a shortstop, all things manager Pete Mackanin and bench coach Larry Bowa have raved about in recent days. He’s even been called “the most underrated player” in the league.

Whether you believe that or not, it’s clear the team values Galvis. J.P. Crawford, long the team’s top prospect, has struggled offensively during his year-long stint in AAA, although he has a slash line of .260/.372/.548, with an OPS of .920, a 15.1% BB-rate and a 15.1% strikeout rate, all while playing good defense.

With Galvis under team control through next year, the Phillies have time to let that situation play out. But at some point in the near future, a decision will have to be made there, too.

And what about the outfield? Aaron Altherr sure seems like a building block, and Nick Williams has looked good in his brief time with the Phillies. It seems like those two are locks to be starters in 2018. Odubel Herrera is signed through 2023, so you would think the outfield is set moving forward. But Herrera has struggled to the tune of a .256/.292/.396 slash line this season, and lapses in concentration could have Klentak questioning his long-term viability. Might he look to deal the former All-Star?

And what about the persistent reporting from Cafardo who, for the second time, is pushing the Phils as potential trade partners for Giancarlo Stanton and Christian Yelich? Is there any fire to this smoke? And if so, which prospects would get dealt in order to make a deal like that happen?

How are the Phillies going to get an ace-quality starting pitcher on this team? Perhaps Aaron Nola is turning into that guy, but most have his upside pegged as a No. 2 starter on a really good team. Should Klentak be in the free agent market looking at starting pitchers Yu Darvish or Johnny Cueto? How about after 2018 when Dallas Keuchel and Clayton Kershaw likely become free agents?

Doing so would fly in the face of the stated goal of the front office to buy the bats and develop the arms.

Klentak could use his deep farm system to swing a trade for a controllable young starter like Sonny Gray, Chris Archer, Jose Quintana, or any of the other young, top-of-the-rotation arms that could become available over the next few months. And Klentak also has to build a bullpen. Does he do that with Velasquez closing games?

A general manager’s biggest mistakes are often picking the wrong player. Klentak has a lot of those specific decisions to make over the next year and a half, and what he decides will go a long way in determining whether this rebuild truly is going to take a long time or whether the Phillies can return to contention in the next year or two.

Matt Klentak has clearly had difficult decisions to make already. This is not to say he hasn’t been doing anything or that he’s been just hanging around the club twiddling his thumbs.

But we’re now getting to crunch time with this rebuild, and although he’s been the team’s general manager for nearly two years now, it feels as if the heavy lifting for Klentak is only now just beginning.

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