With Phillies nearing luxury tax, Matt Klentak needs to prove he’s a good GM | Scott Lauber

Halfway through the fifth offseason of a rebuilding project that they hoped would be completed by now, the Phillies have a dirty little secret: Their greatest asset has been the owners' cash.

No team outspent the Phillies over the last two winters, and they flexed their financial muscles again the other day, agreeing on a five-year, $118 million contract with free-agent pitcher Zack Wheeler. Terrific. Kudos to John Middleton and the Buck family for repeatedly putting their money where Middleton’s mouth was all those years ago when he pined for his darn World Series trophy back.

Now, though, the time has come for Matt Klentak to prove he's a good general manager.

All of that spending — $75 million over three years for Jake Arrieta; $50 million over three years for Andrew McCutchen; $23 million over two years for David Robertson; a four-year, $45 million extension for Aaron Nola; $330 million over 13 years for Bryce Harper; and, now, $23.6 million annually through 2024 for Wheeler — has pushed the Phillies' payroll to within sniffing distance of competitive-balance tax territory.

Problem is, their win total topped out at 81 this past season, and it will take more than the additions of Wheeler and new manager Joe Girardi to chase the 90 to 92 victories that likely will net a National League wild-card spot.

The Phillies’ reimagined roster still lacks a third baseman or shortstop and, at a minimum, one more starting pitcher and two or three relievers. They can’t throw money at each of those needs, either. Eventually, that well runs dry or gets capped when the meter hits $208 million, the tax threshold that Middleton has said he’s willing to exceed only if the Phillies have a real chance to win the World Series.

Not even Middleton can believe that they’re close to that level yet.

So, with the winter meetings set to begin Sunday night in San Diego, the directive to Klentak is perfectly clear: Get creative.

Payroll estimates tend to vary depending on the source. Once Wheeler passes his physical and his contract becomes official, the Phillies will have roughly $189 million committed against the competitive-balance tax in 2020, according to Cot’s Baseball Contracts, leaving them about $19 million to address their myriad needs.

(An aside: It could be argued that Middleton should green-light going over the tax threshold for the first time in franchise history. The penalty for first-time offenders — a 20% tax on every dollar spent up to $228 million — is relatively minor, and with Arrieta and Robertson coming off the books after next season, the Phillies should easily get back below the bar in 2021. Still, shouldn’t $208 million be enough for Klentak to build a playoff team?)

It’s imperative that the Phillies’ most highly touted young players — right-hander Spencer Howard and power-hitting Alec Bohm, who Klentak insists the Phillies still believe can play third base — graduate to the majors.

It would help, too, if Adam Haseley proves capable of being the everyday center fielder and joins Nola, Scott Kingery, and Rhys Hoskins in the group of relatively cost-controlled homegrown regulars on the roster.

But Klentak needs to find a few bargains, too. Who will be this winter’s versions of infielder D.J. LeMahieu and pitcher Lance Lynn, free agents a year ago who outperformed their contracts in the first season with their new teams?

With so many innings-gobbling mid-rotation and back-end starters on the market (Wade Miley, Rick Porcello, Tanner Roark, Julio Teheran, and on and on), some are bound to slip through the cracks and sign a below-market deal.

Better still, the Phillies might have to pull off a trade or two without the benefit of a deep farm system. Klentak packaged prized pitching prospect Sixto Sanchez to the Miami Marlins in the J.T. Realmuto trade. But the Phillies are rightfully intent on keeping Howard and Bohm, which means identifying a player who is undervalued by his current organization and working out a deal that doesn’t include high-end minor-league talent.

One of Klentak’s first trades as a general manager still ranks as one of his best. In December 2015, he sent minor-league pitcher David Whitehead to the Pittsburgh Pirates for right-hander Charlie Morton, a swap that qualifies as a steal even though Morton made only four starts for the Phillies in 2016 before injuring his hamstring and going on to late-career stardom the following year with the Houston Astros.

There needs to be more where the Morton trade came from.

Didi Gregorius is a primary target to fill the Phillies’ infield vacancy. The free-agent shortstop played for Girardi with the New York Yankees and remains one of the manager’s favorites. He made $11.75 million this year and may fit within the Phillies’ budget, especially because of the apparent paucity of contending teams that are looking for a shortstop. The Cincinnati Reds, one of the more aggressive teams this winter, are believed to have interest.

“I think there are a lot of different directions we can go,” Klentak said recently. “Obviously, that’s a balancing act. Any resources we devote to the offensive side will take away the resources we have to spend on the pitching side. So we have to balance that as well as we can.”

Indeed, even if the Phillies land Gregorius, they will need to hit on a few players, specifically pitchers, who fit into the “buy-low” bin where Pat Gillick once turned up Jayson Werth, J.C. Romero, and Chad Durbin.

Klentak hasn’t had enough of those finds since taking over as general manager after the 2015 season. The rest of this winter might be a referendum on whether or not he’s able to do more than merely spend the owners’ money.