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The Phillies have a pivotal offseason ahead of them, as the club is still seeking its first playoff berth since 2011 despite a concerted effort to emerge from a multi-year rebuilding process. With manager Gabe Kapler dismissed in favor of veteran Joe Girardi, the pressure on the front office is mounting to put together a winning unit.

Guaranteed Contracts

  • Bryce Harper, OF: $300MM through 2031
  • Jean Segura, SS: $43.75MM through 2022 (including $1MM buyout of 2023 option)
  • Andrew McCutchen, OF: $40MM through 2021 (including $3MM buyout of 2022 option)
  • Aaron Nola, RHP: $39MM through 2022 (including $4.25MM buyout of 2023 option)
  • Scott Kingery, INF/OF: $20.5MM through 2023 (including $1MM buyout for 2024)
  • Jake Arrieta, RHP: $20MM through 2020
  • Odubel Herrera, OF: $19.5MM through 2021 (including $2.5MM buyout of 2022 option)
  • David Robertson, RP: $13MM through 2020 (including $2MM buyout for 2021)
  • Jay Bruce, OF: $13MM through 2020 (Mariners are paying $11.625MM)

Arbitration-Eligible Players (projections via MLBTR contributor Matt Swartz)

Option Decisions

  • Jason Vargas, LHP: Phillies declined $8MM option in favor of $2MM buyout
  • Pat Neshek, RP: Phillies declined $7MM option in favor of $750K buyout
  • Jared Hughes, RP: Phillies declined $3MM option in favor of $250K buyout

Free Agents

Over the past two winters, the Phils have added the likes of Bryce Harper, Andrew McCutchen, Jake Arrieta and David Robertson via free-agent deals while swinging high-profile trades to acquire J.T. Realmuto and Jean Segura (among others). The directive from ownership and the front office alike has been clear: bring playoff baseball back to Philadelphia. Hard as it may be to believe, the Phillies haven’t played a postseason game since 2011, when their roster featured the dominant trio of Cliff Lee, Cole Hamels, and the late Roy Halladay. (Roy Oswalt wasn’t exactly a shabby fourth starter, either.)

Aggressive as they’ve been, however, the Phillies simply haven’t been able to sustain a season’s worth of winning ways. The 2018 and 2019 Phillies each had clear talent, as both iterations of the team enjoyed a lengthy run in first place in the NL East. However, those two most recent versions of the Phils also faceplanted in stunning fashion late in the season and were left at or just shy of the .500 mark. Now, fourth-year GM Matt Klentak is feeling more pressure to construct a winner than ever before.

The clearest area for improvement is on the pitching staff, where Philadelphia hurlers were a nearly across-the-board disappointment — so much so that pitching coach Chris Young was jettisoned after just one year on the job. Bryan Price, who like Girardi is a seasoned dugout veteran, will step into Young’s place and work to improve upon a Phillies rotation that posted a lowly 4.64 ERA (4.91 FIP) and a bullpen that wasn’t much better (4.38 ERA, 4.84 FIP).

In the rotation, Aaron Nola is really the Phillies’ only surefire bet to be an above-average starter. The 2019 season certainly wasn’t Nola’s best, but the 26-year-old has cemented himself as a quality workhorse upon whom the club can rely. Jake Arrieta was once described similarly, but he struggled in 2019 while pitching through a bone spur in his elbow and ultimately succumbed to season-ending surgery. At 34 years of age in March, the former Cy Young winner is somewhat of a wild card in the rotation.

The 2019 Phillies opted to forgo veteran rotation additions and instead leaned heavily on Zach Eflin, Nick Pivetta and Vince Velasquez, entrusting the balance of its Opening Day rotation spots to that young trio. Of the three, only Eflin delivered useful results — and even he briefly lost his grip on a rotation spot and found himself sojourned to the bullpen. Through 163 1/3 innings, the 25-year-old notched a 4.13 ERA with 7.1 K/9, 2.6 BB/9 and a 44.6 percent ground-ball rate. Eflin’s 1.54 HR/9 mark was higher than one would like (hence his 4.85 FIP), but his bottom-line results were plenty serviceable. The same can’t be said for the 26-year-old Pivetta or the 27-year-old Velasquez. Pivetta logged a brutal 5.74 ERA as a starter, while Velasquez was only a bit better (4.96 ERA in the rotation).

It can be argued that the Phillies should have a greater sense of urgency than any other team in MLB when it comes to adding to the rotation (particularly now that Jake Odorizzi accepted a qualifying offer in Minnesota, giving the rotation-needy Twins a bit more stability). Fortunately, it’s a deep class of starting pitching headlined by a pair of bona fide, franchise-altering aces in the form of Gerrit Cole and Stephen Strasburg. But, while the Phillies have been as aggressive as anyone on the open market in recent seasons, Klentak has suddenly offered a more measured approach with regard to free agency.

“One of the things we’ve got to try to do, if we can, is to not forfeit draft picks, and that’s hard when you’re fishing in the deep end of the free-agent pond,” Klentak said in a recent appearance on the 94 WIP Midday ShowBut we lost our second-round pick last year and our second and third the year before. That doesn’t sound like a lot, but that’s where Scott Kingery comes from. That’s where Spencer Howard comes from. That’s where Connor Seabold comes from. … We’ve got to try to hang onto that as much as we can.”

Perhaps Klentak was merely doing everything in his power to avoid doubling down on owner John Middleton’s “stupid money” decree a year ago this time, but those comments don’t sound like a portent for a run at Cole or Strasburg. Middleton could, of course, take matters into his own hands, but Klentak’s recent sentiment is surely of note.

If the organizational preference is indeed to add rotation help — and Klentak did plainly state a need to address the starting staff in that same interview — then the top names on the Phillies’ radar would likely be Hyun-Jin Ryu and old friend Cole Hamels, who has already expressed interest in a return to the Phils. Other notable names lacking a qualifying offer include Dallas Keuchel, Michael Pineda, Rick Porcello, Tanner Roark, Julio Teheran and Kyle Gibson. While no one from that bunch is of the same caliber as the Cole or Strasburg — Ryu may not be far off, but his durability is a perennial question mark — the Phils do have options to round out the rotation if they prefer to hang onto their draft choices.

As always, the trade market will present innumerable alternatives. Corey Kluber, Matthew Boyd, Chris Archer, Jon Gray, Robbie Ray, Marco Gonzales and (depending on the direction the Red Sox go) Eduardo Rodriguez are all, at the very least, plausible winter trade candidates. Other, less-expected names will surely surface as well.

There’s also reason to believe the Phillies will work to improve their relief corps. The club’s relief unit — like those of the rest of the NL East teams — was not a strength in 2019. Closer Hector Neris is a solid performer at the back of the unit. Pitchers such as Jose Alvarez, Seranthony Dominguez, and Ranger Suarez showed some promise. Victor Arano could be a big asset if he can return to health. But there’s obviously room for improvement. Klentak could consider any and all remaining open-market options, though he’d need to hit the trade market if he prefers to pursue a tried-and-true closer type.

Looking at the team’s lineup, there are nearly as many questions as answers. J.T. Realmuto will once again be the team’s primary catcher in 2020 — and perhaps for years to come if the two sides can come to terms on an extension, which is another key winter priority for Klentak and his staff. Bryce Harper is now entrenched in right field, and a healthy Andrew McCutchen will return from an ACL tear to man the other outfield corner. On the infield, first baseman Rhys Hoskins will look to rebound from a terrible second half, and Jean Segura is signed through 2022. Scott Kingery will be in the mix somewhere, but his ability to play third base, second base, shortstop and the outfield gives the Phils quite a bit of flexibility.

They’ll need it, particularly with the possibility of non-tendering Maikel Franco and Cesar Hernandez. The latter of the two has generally been a solid second baseman but could see his arbitration price climb north of $11MM in 2020, which is an untenable financial arrangement, especially with a free agent market loaded with veteran alternatives. The former, meanwhile, has struggled immensely and never fully delivered on his once ballyhooed prospect status. And then there’s center fielder Odubel Herrera, who was suspended 85 games under MLB’s domestic violence policy and isn’t guaranteed a place in the organization moving forward. (And even before that ban, Herrera wasn’t producing at the plate.)

The Phillies, then, could explore the market for third basemen, second basemen and/or center fielders depending on how they want to play their cards. The infield offers ample possibilities, with Anthony Rendon, Josh Donaldson and Mike Moustakas all available in free agency and a host of serviceable (but unspectacular) second basemen on the market as well. Rendon and Donaldson have qualifying offers attached to them, so if the Phillies are indeed avoiding such free agents, they’d likely look to Moustakas as the headlining free-agent option. A pursuit of Didi Gregorius may not be an immediately obvious fit, but Segura could move to either second or third base to facilitate that type of deal. (And on cue, there’s now reporting to suggest this could indeed be a consideration.)

The center field market is rather thin, with only Brett Gardner and Shogo Akiyama representing viable regulars in free agency. But the trade market offers a natural fit in Pirates center fielder Starling Marte. The Phillies could also line up with the Red Sox on a Jackie Bradley Jr. deal.

The Phillies, though, have the financial means and the urgency needed to go searching for a bigger fish. If the Red Sox truly are going to explore moving Mookie Betts, he’d look mighty fine roaming center field in Philly for the 2020 season (if not beyond). There’s been plenty of speculation about the possibility of the Cubs moving Kris Bryant this winter, and the Phils have a need at the hot corner. Francisco Lindor‘s name is out there, too; clearing the way for him at short would easily be worth the trouble. The Phillies don’t have the deepest of farm systems, but there’s every reason for Klentak to push the envelope and try to bring a winner to Citizens Bank Park.

Some may question whether the Phillies can plausibly afford to spend much after last year’s free-agent bonanza, but on an annual basis, Harper’s record deal isn’t really that cumbersome. The Phillies have about $167MM on the 2020 books — if you include all of the projected arbitration salaries. Jettisoning Hernandez and Franco, for instance, would trim $18.5MM from that sum.

In terms of luxury tax considerations, the club is at a manageable $186MM (including Hernandez and Franco). At this point, it’s hard to justify drawing a hard line at that $208MM barrier. The Phillies were extremely aggressive last winter, are trying to extend Realmuto and have no designs on going back into rebuild mode at any point in the near future. Treating the luxury threshold as a salary cap would be a suddenly weak-hearted change of course to what has been an aggressive pursuit — particularly given the fact that as a first-time offender, the only real penalty they’d face would be a 20 percent overage fee on their first $20MM. That’s a $4MM slap on the wrist even if they cross the plane by as much as $20MM. And with Arrieta, Robertson and several arbitration players off the books next winter, dipping back beneath the line shouldn’t be that difficult.

The Phillies may have a tough road to contention given the strength of their division rivals, particularly those in Atlanta and D.C., but their direction remains obvious. We’re talking about a big-market, high-payroll club that hasn’t been to the playoffs in nearly a decade, has a GM entering his fifth season, and is only nine months removed from signing a player to the largest free-agent contract the sport has ever seen. The Phillies should and will aggressively add to the roster this winter.

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