Phillies Matt Klentak throwing his hat into Executive of the Year race

The Phillies aggressiveness could land Matt Klentak some hardware next offseason, but it depends on if he can finish it off this year.

Fans and analysts knew the Phillies were going to be aggressive going into the 2019 season. Some expected a completely different lineup going into opening day with players such as Cesar Hernandez, Maikel Franco, Odubel Herrera, and Carlos Santana on the trade block.

General Manager Matt Klentak had a lot of pressure thrown on him early with owner John Middleton’s “stupid money” comments. Those comments added with superstars being available in free agency and the fan’s expectations to turn over the roster made Klentak’s job even tougher than anticipated.

In his fourth offseason with the Phillies Klentak has made an array of moves both in free agency and on the trade market. He voided the Phillies of Santana’s contract and upgraded from J.P. Crawford with the Seattle trade that brought over Jean Segura, James Pazos, and Juan Nicasio.

Getting rid of Santana’s contract, upgrading at shortstop, improving the bullpen, and moving Rhys Hoskins back to first base made this deal, on the surface, a fantastic one to start the offseason.

Klentak quietly added another bullpen arm when he swapped pitcher Luis Garcia to the Angels for lefty Jose Alvarez, who replaces Luis Avilan. Garcia is an inconsistent mess and this deal makes little sense on the surface for Los Angeles.

In free agency, the Phillies brought in David Robertson, one of the most consistent relievers in baseball, and Andrew McCutchen, a former MVP who brings leadership and a winning culture into the young clubhouse.

The Robertson deal, which was negotiated by Robertson himself, for two-years $23 million looks like an absolute steal at this moment given his success and versatility in the back of the bullpen.

Giving McCutchen three years might have been a bit much, but he’s an important player who gives the lineup credibility. If a prospect like Adam Haseley or Mickey Moniak comes up at some point and outperforms McCutchen then the Phillies could swap the former MVP for another piece down the road.

On Thursday, Klentak added another big move to his resume by going all in with J.T. Realmuto, arguably the best catcher in baseball. While the organization was forced to give up top prospect Sixto Sanchez and two promising young players in Jorge Alfaro and Will Stewart, Realmuto instantly makes Philadelphia better.

In four months Klentak has added four All-Stars, and he isn’t anywhere close to being done yet.

The organization is expected to sign either Bryce Harper or Manny Machado this offseason, and getting a deal done with either one will automatically launch Klentak atop the leaderboard for Executive of the Year.

In addition, the Phillies could still sign pitchers Dallas Keuchel and/or Craig Kimbrel. Adding either to the roster would launch the Phillies into a pennant discussion regardless of what happens with Harper and Machado.

If Klentak can’t make a deal for a superstar, there will be mass disappointment across the city and his credibility will take a hit as a GM who can’t sign big-time players despite having stupid money after failing to bring over J.A. Happ and Patrick Corbin.

As the Phillies roster stands right now Klentak looks like the clear-cut candidate to win Executive of the Year, but he still has a ways to go this offseason to make this team better.