{"numbering":"no_numbering","slides":[{"title":"Jeremy Hellickson for Sam McWilliams","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Hellickson_J_Getty_817156954.jpg","credit":"Getty Images","published":1602118661,"caption":"

Less than a month after he was hired as Phillies GM, Klentak's first trade was with Arizona for Hellickson. It was a good trade, as the minor-leaguer the Phillies gave up has made only 11 appearances above Double A, while Hellickson was effective here.

In 52 starts with the Phillies, Hellickson went 18-15 with a 4.09 ERA and 1.19 WHIP.

It's not a good thing, however, that until Zack Wheeler arrived, Hellickson was the Phillies' second-best starting pitcher during the Klentak era, behind Aaron Nola.

The Phillies traded Hellickson to Baltimore ahead of the 2017 deadline for Hyun-Soo Kim and Garrett Cleavinger. Cleavinger made his Phillies debut this summer, his lone appearance, and allowed a home run to the first batter he faced, Robinson Cano.

"},{"title":"Charlie Morton for David Whitehead","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Morton_C_Getty_523569074.jpg","credit":"Getty Images","published":1602119337,"caption":"

We recently wrote about Morton when the Phillies' season ended in Tampa. His start against Vince Velasquez in the first game of that series was symbolic of the lack of viable starting pitching Klentak built.

The Phillies had Morton for one season and he made four starts before tearing his hamstring while running out a sacrifice bunt. The Phillies let him walk after the season and he's since signed a pair of team-friendly two-year deals.

In 97 starts since leaving the Phils, Morton is 47-18 with a 3.34 ERA and 100 more strikeouts than innings pitched. In nine playoff starts, he's 5-2 with a 3.50 ERA.

This was a very good trade by Klentak, but he didn't have the foresight to keep Morton in the fold. If he did and Morton succeeded here in 2017 as he did in Houston, maybe the Phillies never sign Jake Arrieta.

"},{"title":"Ken Giles for Vince Velasquez, 4 others","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Giles_K_Getty_959985154.jpg","credit":"Getty Images","published":1602119365,"caption":"

Trading Giles was logical in 2015 because the Phillies were so far away from contention but had a 24-year-old flamethrowing closer with a 1.56 ERA in 113 appearances. Giles was also at his cheapest so his value was never going to be higher.

The problem is the Phillies brought back five players in the trade with the Astros and none of them panned out. Vince Velasquez has a 4.72 ERA as a Phillie and has not seized a role as a starter or reliever despite opportunity after opportunity.

The other players the Phillies brought back were former first overall pick Mark Appel, Tom Eshelman, Brett Oberholtzer and Harold Arauz, all pitchers. Appel's pro career ended quickly, Eshelman was traded to Baltimore for practically nothing, Oberholtzer lasted a half-season and Arauz is now playing overseas.

"},{"title":"Jesse Biddle for Yoervis Medina","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Biddle_J_Getty_578704618.jpg","credit":"Getty Images","published":1602119387,"caption":"

The Phillies did not feel that Biddle, their first-round pick in 2010, could help the big-league team and traded him to Pittsburgh for reliever Yoervis Medina.

Medina had a 2.82 ERA with the Mariners in his first two big-league seasons but never pitched for the Phillies and has not appeared in the majors since 2015.

Biddle never appeared in the majors for the Phillies either. He's pitched for four teams over the last three seasons: the Braves, Mariners, Rangers and Reds.

"},{"title":"Jimmy Paredes","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Paredes_J_Getty_607556950.jpg","credit":"Getty Images","published":1602119420,"caption":"

Not much to say about this one. The Phillies acquired the utilityman Paredes for cash from Toronto in 2016 and he hit .217 in 150 plate appearances.

"},{"title":"Carlos Ruiz traded to Dodgers","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Ruiz_C_Getty_606085926.jpg","credit":"Getty Images","published":1602119434,"caption":"

As weird as pictures like this still look, Chooch was no longer vital to the Phillies at this point. He had 193 decent plate appearances with the 2016 Phils before they traded him to the Dodgers for veteran catcher A.J. Ellis and pitcher Tommy Bergjans, who last appeared in 2018 with the Reds' Single A affiliate.

"},{"title":"Pat Neshek","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Neshek_P_Getty_1145308971.jpg","credit":"Getty Images","published":1602119451,"caption":"

It was an interesting three years with Neshek. The Phillies acquired him for cash from the Astros in November 2016. Neshek was then awesome here in 2017, posting a 1.12 ERA in 43 appearances before being traded to the Rockies for three minor-leaguers: pitchers J.D. Hammer and Alejandro Requena and infielder Jose Gomez.

Hammer made 20 appearances with the 2019 Phillies and pitched OK, but he was lit up when he went back down to Triple A. Requena and Gomez last appeared at Single A Clearwater in 2019.

The Rockies had Neshek for two months and then the Phillies re-signed him in free agency to a two-year, $16.25 million contract. And that's when things went south. Neshek made just 50 combined appearances in those two seasons because of injuries and limitations to his workload. He sure never saw eye to eye with previous Phils manager Gabe Kapler.

"},{"title":"Howie Kendrick for Darin Ruf","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Kendrick_H_Getty_801569194.jpg","credit":"Getty Images","published":1602119505,"caption":"

Klentak and the Phillies had the right idea acquiring Kendrick from the Dodgers for Darin Ruf and Darnell Sweeney. Kendrick is a productive, dangerous hitter. But he doesn't serve much of a purpose on a non-contender.

The Phillies traded for him in November 2016, then dealt him to the Nationals in July 2017 for minor-league lefty McKenzie Mills.

Kendrick hit .340 with the Phillies and has hit .320 since 2017, winning a world series in D.C.

"},{"title":"Clay Buchholz","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Buchholz_C_Getty_667815720.jpg","credit":"Getty Images","published":1602119519,"caption":"

Emblematic of Klentak's faulty decision-making and bad luck with starting pitchers.

The Phillies traded for Buchholz's $13.5 million salary after a poor year in Boston. Buchholz made two starts here, allowed 10 runs and was done for the season with a forearm/elbow injury.

Buchholz made nearly as much in that one year as Morton received in his two-year deal from the Astros ($14M guaranteed).

"},{"title":"Ty Kelly","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Kelly_T_Getty_854921870.jpg","credit":"Getty Images","published":1602119537,"caption":"

Utilityman acquired for cash. Maybe the funniest former player on Twitter. Kelly appeared in 69 games with the Phillies and even had a walk-off hit on July 29, 2017 against the Braves.

"},{"title":"Joaquin Benoit for Seth McGarry","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Benoit_J_Getty_824370874.jpg","credit":"Getty Images","published":1602119552,"caption":"

The Phillies' offseason ahead of 2017 was dreadful. They committed $29 million to Buchholz, Michael Saunders and veteran reliever Joaquin Benoit.

Buchholz made two starts, Benoit was traded eight months later and Saunders hit .205 in 61 games before being let go.

Benoit was traded to Pittsburgh for right-hander Seth McGarry. Now 26, McGarry is essentially an organizational depth piece. He had a 6.15 ERA in 20 appearances at Triple A last year.

"},{"title":"Juan Nicasio","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Nicasio_J_Getty_1171229342.jpg","credit":"Getty Images","published":1602119565,"caption":"

The Phillies actually acquired Nicasio two years in a row. They traded minor-league utility infielder Eliezer Alvarez for Nicasio in September 2017 and he made two appearances here before reaching free agency.

Nicasio then signed with the Mariners, who traded him to the Phillies in the Jean Segura deal we will get to later. Nicasio was bad with the Phillies and allowed six runs in 1⅓ innings this season with the Rangers. His big-league days may be over.

"},{"title":"Freddy Galvis for Enyel De Los Santos","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Galvis_F_Getty_854895138.jpg","credit":"Getty Images","published":1602119579,"caption":"

A defensive whiz at shortstop and a true iron man. From 2015-18, Galvis played 633 of a possible 648 games, including all 162 in 2017 and '18.

Galvis has never hit for a high average or high OBP, but he's surprisingly developed power as a major-leaguer. Galvis hit 68 home runs in his last four full seasons and went deep seven times this summer.

The Phillies traded Galvis in December 2017 to the Padres for right-handed pitcher Enyel De Los Santos, who appeared 12 times with the Phillies in 2018 and '19 but didn't seem to instill much confidence in Phillies decision-makers, who bypassed him repeatedly when they had needs in the rotation and bullpen.

"},{"title":"Asdrubal Cabrera for Franklyn Kilome","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Cabrera_A_Getty_1040647858.jpg","credit":"Getty Images","published":1602119594,"caption":"

Kilome was at one point an intriguing Phillies pitching prospect. He was ranked 10th in their system by MLB.com when he was traded to the Mets for Asdrubal Cabrera.

One of the Phillies' many marginal pickups around the 2018 trade deadline, Cabrera had a forgettable two months here.

Kilome, 25, had Tommy John surgery and missed all of 2019. He made his MLB debut this summer with the Mets and allowed 14 earned runs in 11⅓ innings.

"},{"title":"PTBNL for Wilson Ramos","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Ramos_W_Getty_1034434530.jpg","credit":"Getty Images","published":1602119610,"caption":"

Offensively, Ramos was awesome here in a small sample, hitting .337 in 101 plate appearances. But by the time he got here he could barely catch and has only become more of a liability the last two years with the Mets.

This was a good deal for the Phillies, though, who were starting an unproven Jorge Alfaro at that point. They didn't have to give up anything to get Ramos.

"},{"title":"Aaron Loup for Jacob Waguespack","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Loup_A_Getty_1027228662.jpg","credit":"Getty Images","published":1602119632,"caption":"

The Louper! The lefty specialist made nine appearances here before departing in free agency.

He resurfaced with the Rays this season and was excellent with a 2.52 ERA in 25 innings.

To acquire Loup from Toronto in July 2018, the Phillies traded former 37th-round pitcher Jacob Waguespack. Improbably, Waguespack advanced all the way to the majors by 2019. He has a 5.08 ERA in 27 games.

"},{"title":"Justin Bour for McKenzie Mills","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Bour_J_Getty_1064407824.jpg","credit":"Getty Images","published":1602119765,"caption":"

The Phillies traded lefty minor-league McKenzie Mills, acquired from the Nats for Howie Kendrick, to the Marlins for Justin Bour in August 2018. They looked at Bour then as a player capable of filling the power-bat-off-the-bench role they eventually acquired Jay Bruce to play.

Bour strained his oblique early in his Phillies run and ended up going just 11 for 49 (.224) with one homer. He was granted free agency after the season.

"},{"title":"Luis Avilan for Felix Paulino","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Avilan_L_Getty_1036245664.jpg","credit":"Getty Images","published":1602119791,"caption":"

Acquired as an extra lefty down the stretch for the 2018 Phillies. Avilan was OK as a rental. Nothing special. He made 12 appearances but pitched just 5⅔ innings in the days before the three-batter rule.

Paulino has made 14 appearances above Single A.

"},{"title":"Jose Bautista","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Bautista_J_Getty_1065285608.jpg","credit":"Getty Images","published":1602119832,"caption":"

Acquired for nothing from the Mets. All of these moves late in 2018 were for veteran rentals who could maybe luck into an effective couple of games that key wins. Obviously, the Phillies needed more to stay in the hunt.

This was Bautista's last major-league stop. He hit .244/.404/.467 in 57 plate appearances with two homers.

"},{"title":"Jean Segura for Carlos Santana & J.P. Crawford","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Segura_J_Getty_1277397730.jpg","credit":"Getty Images","published":1602119855,"caption":"

The Phillies unnecessarily boxed themselves into a corner by signing Santana and unsuccessfully trying to play Rhys Hoskins in left field.

Then this deal materialized, solving that logjam while also upgrading the Phillies at shortstop. The evaluation of this trade really depends on how you view Segura and Crawford. I have never seen Crawford as a Top 20 shortstop. He's never proven he can hit.

Segura has his flaws too. A year after the trade, the Phillies moved him off of shortstop. There's no denying that he can hit. He's hit .298 with runners in scoring position in each year as a Phillie.

The 2019 and 2020 Phillies cared more about making the playoffs and Segura gave them a better chance than Crawford would have over the same span.

"},{"title":"Jose Alvarez for Luis Garcia","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Alvarez_J_Getty_1269203090.jpg","credit":"Getty Images","published":1602119880,"caption":"

One of Klentak's best trades as Phillies GM. He flipped mediocre-but-hard-throwing right-handed reliever Luis Garcia to the Angels for lefty specialist Jose Alvarez.

Alvarez had a 3.17 ERA here in 75 appearances across two seasons and is worth looking into bringing back.

Garcia has a 4.73 ERA over that span, also in 75 appearances.

"},{"title":"J.T. Realmuto for Sixto Sanchez, Jorge Alfaro, Will Stewart","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Realmuto_J_Getty_1271930550.jpg","credit":"Getty Images","published":1602119902,"caption":"

Obviously the most-discussed trade of Klentak's five-year run as Phillies GM. The Phillies traded their top prospect Sixto Sanchez (at a point when Sanchez's value was decreasing because he was injured and out of shape) along with catcher Jorge Alfaro and pitcher Will Stewart to Miami for the best catcher in baseball.

Realmuto has been very good here, even better than he was in Miami. Sanchez bounced back from that rocky period and debuted this summer with the Fish. He looked like an ace in the making.

If the Phillies can't re-sign Realmuto, especially after failing to finish with a winning record either year he was here, this trade will go down as a big fail. Especially with Sixto looking so far ahead of the Phillies' top pitching prospect, Spencer Howard.

At the time the Phillies made this trade, Howard had equal value to Sanchez, maybe more.

"},{"title":"Jay Bruce for almost nothing","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Bruce_J_Getty_1153922057.jpg","credit":"Getty Images","published":1602119925,"caption":"

The Phillies acquired Bruce to be their first bat off the bench just before Andrew McCutchen tore his ACL in San Diego, thrusting Bruce into everyday duty.

Bruce had a huge first month with the Phillies and has been an impactful power bat when healthy. He just hasn't been healthy enough.

There was $21.3 million remaining on Bruce's contract when the Phillies acquired him but they had to pay just $2.75 million of that.

Maybe Klentak's best trade, which isn't saying much.

"},{"title":"Brad Miller","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Miller_B_Getty_1178215047.jpg","credit":"Getty Images","published":1602119952,"caption":"

The Yankees traded Miller to the Phillies for cash and he proceeded to slug .610 here and hit 12 homers in 130 plate appearances.

Keeping him would have been ideal but Miller wanted more of a role elsewhere. He found it with the Cardinals this season as their everyday DH and cleanup hitter. He hit .232 with an .807 OPS, though he slumped late.

"},{"title":"Mike Morin","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Morin_M_Getty_1174930327.jpg","credit":"Getty Images","published":1602120044,"caption":"

Blah. The Phillies needed more bullpen help than Klentak found them at the 2019 trade deadline. The Phillies went the clearance route, bringing in guys like Morin, Blake Parker and Jared Hughes for free.

Morin had a 5.79 ERA in 29 appearances.

"},{"title":"Jason Vargas","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Vargas_J_Getty_1171576443.jpg","credit":"Getty Images","published":1602120070,"caption":"

You sure couldn't blame Phillies fans for being disappointed with this trade since Vargas was the only starting pitcher the starting pitching-needy Phillies added at the 2019 deadline.

He went 1-4 with a 5.37 ERA in 11 starts as a Phillie. Truthfully, though, he kept them in games. He allowed two earned runs or fewer in six of his 11 starts. The Phillies just needed more — way more.

"},{"title":"Corey Dickerson","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Dickerson_C_Getty_1174001564.jpg","credit":"Getty Images","published":1602120106,"caption":"

If the Bruce acquisition was Klentak's best trade, this would be 1B. But, again, we are talking about a short-term acquisition of a role player, so that's an indictment in a way.

Dickerson has always been a quality left-handed hitter with a line-drive approach. It was a skill set the Phillies needed in 2019 and could have used again in 2020 had they known the NL would be adopting the designated hitter for the shortened season.

The Phillies landed Dickerson from a fledgling Pirates team for international bonus money. Dickerson hit .293 with an .886 OPS in 137 plate appearances as a Phillie, driving in 34 runs in 34 games.

Without an everyday spot here, he signed a two-year, $17.5 million contract with the Marlins. That's the richest contract on Miami's books. He had a disappointing two months with career-lows in batting average (.258), slugging (.402) and OPS (.713).

"},{"title":"Kyle Garlick for Tyler Gilbert","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Garlick_K_Getty_1271430894.jpg","credit":"Getty Images","published":1602120378,"caption":"

The Dodgers had so much talent on their 40-man roster that Garlick, despite a minor-league track record of hitting for power (especially against lefties) became a casualty.

The Phillies acquired Garlick on February 15 for lefty reliever Tyler Gilbert, who had a 2.83 ERA with nearly a strikeout per inning in 36 games with Triple A Lehigh Valley last season. He was behind a handful of lefties on the Phillies' depth chart.

Garlick went just 3 for 22 this season with one double, no homers, no walks and seven strikeouts. He strained his oblique in mid-September, which hurt the Phillies as outfield injuries mounted.

"},{"title":"Edgar Garcia to Tampa","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Garcia_E_Getty_1227685108.jpg","credit":"Getty Images","published":1602120469,"caption":"

The Rays seemingly turn every reliever into the best possible version of himself. If that happens with Garcia, who the Phillies sent to Tampa for nothing but a PTBNL ...

"},{"title":"David Hale for Addison Russ","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Hale_D_Getty_1228659587.jpg","credit":"Getty Images","published":1602120510,"caption":"

This trade was criticized because Hale is a mediocre long-man and Russ had a 2.54 ERA with 12.9 strikeouts per nine at Double A last year.

There is fine print, though. The Phillies would have had to add Russ, a 26-year-old former 18th-round pick, to their 40-man roster this winter or risk losing him for nothing in the Rule 5 draft. If they weren't going to do that, trading him made sense.

Hale had almost no impact on the Phillies, who were desperate for any form of bullpen help. He appeared in six games, started two bullpen games and allowed five runs on 16 hits in 11 innings.

If Russ does end up positively affecting a major-league bullpen over the next few seasons, this will go down as a whiff.

"},{"title":"Brandon Workman, Heath Hembree for Nick Pivetta, Connor Seabold","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Workman_B_Getty_1271854029.jpg","credit":"Getty Images","published":1602120545,"caption":"

The Phillies had the worst bullpen in baseball when the "reinforcements" arrived from Boston. Those reinforcements were worse than any Phillies incumbent.

Workman and Hembree, in 25 combined appearances as Phillies, had a 9.27 ERA and 2.42 WHIP. Unimaginably bad.

Workman is a free agent and Hembree is a non-tender candidate.

Pivetta left here with the highest ERA in Phillies history by any Phillie who pitched as many innings as he did. Seabold was one of their better pitching prospects.

This trade will go down as a total disaster if either Pivetta or Seabold sticks in the Red Sox rotation.

"},{"title":"Austin Davis","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Davis_A_Getty_1270511088.jpg","credit":"Getty Images","published":1602120590,"caption":"

It's shocking the Phillies got anything for Davis, a below-average lefty who doesn't do a good job of retiring lefties or righties. Davis had a 5.66 ERA here in 50 appearances.

The Phillies traded him to Pittsburgh for minor-league righty Joel Cesar, a hard thrower with some promise.

"},{"title":"David Phelps","image":"https://www.nbcsports.com/sites/rsnunited/files/slide/image/Phelps_D_Getty_1276808486.jpg","credit":"Getty Images","published":1602120645,"caption":"

This was a good deal by Klentak despite how poorly Phelps pitched in the month after he was acquired. Phelps had a 2.85 ERA from 2016 until the day he was traded to the Phillies.

It was strange that Milwaukee even traded Phelps, who at that point had a 2.77 ERA with 20 strikeouts and two walks in 13 innings.

The Phillies sent three low-level pitchers to Milwaukee to complete the trade: Brandon Ramey, Juan Geraldo and Israel Puello.

Phelps was baaaaad in September but his track record means more than a few weeks here. His stuff was not worse than it was in Milwaukee. He has a 2021 club option for $4.5 million, a fair price to retain him.

"}]}

Matt Klentak's complete trade history as Phillies GM