With the trade deadline fast approaching, the Philadelphia Phillies will be looking to make some big moves to bolster their roster ahead of a potential deep playoff run. The Phillies have made numerous trade deals at the deadline over the years. Some of them have worked out better than planned, whereas everyone probably wishes other never happened.

In recent times, the trade with the Pittsburgh Pirates that brought Rodolfo Castro to the Phillies in exchange for pitcher Bailey Falter in 2023 could fall under this category. Castro provided all of three hits, two runs and two RBIs in his 14-game stint with the Phillies in 2023. Falter has gone on to become a mainstay in the Pirates rotation, currently sporting a solid 7-5 record with a 3.82 ERA and 1.18 WHIP in 2025.

But of course, that move is likely nothing compared to some of the atrocious deals made at the deadline by Philadelphia in the past. As a result, let’s take a look back at five of the worst trade deadline moves that the Phillies have made in the recent history of the franchise.

5 of the worst trade deadline deals in Philadelphia Phillies history

2000: Phillies trade Curt Schilling to the Arizona Diamondbacks for Omar Daal, Nelson Figueroa, Travis Lee and Vicente Padilla

Philadelphia may have gotten the steal of the century when they acquired future ace Curt Schilling from the Houston Astros for Jason Grimsley. But they sure gave a lot of that away during the summer of 2000. Amidst their seventh consecutive losing season, the Phillies traded away Schilling to the Arizona Diamondbacks for what turned out to be an underwhelming return package.

Right-hander Nelson Figueroa and left-hander Omar Daal would be gone after just one and two seasons, respectively. Former NL Rookie of the Year finalist first baseman/outfielder Travis Lee lasted three solid years with the Phillies, posting a .258 average and .745 OPS with 149 runs scored, 34 home runs and 174 RBIs in 366 games. Finally, right-hander Vicente Padilla at least helped cushion the blow by staying with Philadelphia for six seasons and pitching in the capacity of both a reliever and a starter. In 162 games, Padilla amassed a 49-49 record with a 3.98 ERA and 1.34 WHIP. However, the Phillies failed to make the postseason during all of those years.

On this date back in 2000, the #Dbacks traded for RHP Curt Schilling.

He proceeded to make an unforgettable impact in the desert, earning a spot on the #GenerationDbacks 20th Anniversary Team: https://t.co/ztE5zAC9gV pic.twitter.com/XKJwfBmqHo — Arizona Diamondbacks (@Dbacks) July 26, 2018

As for Schilling, let’s just say he transformed himself into one of the top pitchers in all of baseball during his time with the Diamondbacks. In his four years with Arizona, he went a stunning 58-28 with a 3.14 ERA and 1.03 WHIP, with a whopping 875 strikeouts in 781 2/3 innings. In doing so, Schilling was a two-time All-Star and finished runner-up for the NL Cy Young Award twice.

More importantly, he helped the Diamondbacks to their first and only World Series title in 2001. Just for good measure, Schilling would go on to help the Boston Red Sox to their second World Series win in four years in 2007, proving that he definitely was a winner. Perhaps keeping Schilling could have netted the Phillies with a championship earlier than the one they finally got in 2008.

CHICAGO — The Boeing 757 jet that was supposed to carry the Phillies from New York to Chicago in plenty of time for a fine Sunday night dinner was stuck in Atlanta because of bad weather. So, for six hours, the Phillies were stranded at Yankee Stadium. They played cards. They tried to distract the many children along for the ride on the annual family trip. All they had was time.

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It’s unusual for the club to send its top two executives on the same trip, but Dave Dombrowski and Preston Mattingly are with the team. So they had more time Sunday afternoon to solicit opinions about the upcoming trade deadline. Then, they had time Monday night to watch a potential target, the enigmatic but talented outfielder Luis Robert Jr. He homered and made a diving catch in center during a 6-2 Chicago White Sox win.

There is less time now to make decisions before Thursday’s deadline. The Phillies, according to major-league sources, continue to prioritize a higher-end bullpen addition. They have expressed interest in various hitters, including Robert. But, while there’s been increased trade activity across the league, the Phillies might not find a match until closer to the deadline.

Is there a way to upgrade by Thursday?

“I would think so,” Rob Thomson said.

The Phillies manager has shared his opinions in meetings with the executives.

“I trust other people on that type of stuff,” Thomson said. “They’re the evaluators. I think we’re all on the same page.”

It’s easy to identify the flaws — a missing swing-and-miss reliever for the end of games and a righty power bat. Securing those will require certain sacrifices. There is more demand than supply.

The Phillies have held firm on not wanting to surrender one of their better prospects for a rental player; that stance might have to be altered. Mick Abel has drawn interest from teams, but not as the main piece for a controllable player. He could land the Phillies a good rental, although Abel would qualify as the best prospect Dombrowski has traded for a rental in five years as the Phillies’ president of baseball operations. It is a seller’s market, and everyone knows Dombrowski wants to deal.

He might rather spend the prospect capital on a reliever, but even that would require wading into uncomfortable territory. Shortstop Aidan Miller, a consensus top 50 prospect, has drawn interest. He could be the centerpiece of a major deal.

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Robert, 27, has played in only 13 games this month. He’s had nagging injuries. He has underperformed for two seasons. Contending clubs have viewed him as a buy-low candidate, although the White Sox have larger aspirations.

He has improved his performance in July, perhaps with the hopes of landing in a better situation. His homer, a rare one to come off a Cristopher Sánchez changeup, was the decisive hit Monday night. He hit a hard lineout, then struck out twice. He made the nice grab in center but also allowed Bryce Harper to take an extra base.

He would probably be an upgrade for the Phillies, who scouted the White Sox over the weekend.

“He’s strong,” Thomson said. “He made a heck of a play in the outfield. He’s a strong guy who can really run.”

“He’s a good player,” Sánchez said.

As the market starts to take shape, the lack of righty-hitting outfielders is jarring. The Los Angeles Angels have put a huge price on Taylor Ward, who bashed his 25th homer Monday night. Even if the Phillies liked someone such as the free-swinging but powerful Adolis García, the Texas Rangers now appear to be buyers after a recent hot streak.

It is why Eugenio Suárez, the slugging third baseman for the Arizona Diamondbacks, has drawn so much interest. He is the best available bat.

He is an inelegant fit for the Phillies, and it’s unclear how much interest they have shown. Other contenders have corner infield vacancies Suárez could fill. The Phillies would have to move Kyle Schwarber to left field full-time or have Suárez play third with Alec Bohm at first and Harper in left field.

Harper has said he’s willing to return to the outfield if needed. Schwarber played left field in Sunday’s game at Yankee Stadium. There has not been a conversation about doing it more.

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“I’m open to it,” Schwarber said last week. “I haven’t been asked.”

Thomson said he would be comfortable with a scenario that had Schwarber in left field during the season’s final two months.

“Oh, very,” Thomson said. “I mean, we did that in ’22. It worked out pretty well, and I think he’s moving better now than he did back then.”

Desperation could lead to unconventional solutions. In the last 30 years, three teams have carried three outfielders (minimum 250 plate appearances) with a negative WAR, according to Baseball Reference. They were the 2014 Chicago Cubs, 2012 Houston Astros and 2006 Florida Marlins. The current Phillies would join them.

Though the offense has clicked in July, it’s not because of the outfield. Phillies outfielders have a .566 OPS this month. That ranks 29th in baseball. It’s a .645 OPS since June 1, 28th in baseball. The outfield is 27th in baseball since May 1 with a .666 OPS.

They had a chance to make noise in the sixth inning Monday, down two runs, when Chicago summoned a righty reliever who has a career .932 OPS against lefty hitters to face Max Kepler as the potential tying run. Jordan Leasure needed six pitches, but he coaxed a weak flyout from Kepler.

The Phillies again asked Max Lazar to inherit a sticky situation. He delivered by stranding runners on the corners in the seventh inning. Lazar has inherited 13 runners this season, and none of them has scored. (He permitted a placed runner to score in extra innings last week, but it’s not an earned run.)

Lazar has a 2.96 ERA in 21 appearances. His fastball is sitting 94-95 mph in recent outings. He touched 97 mph last week.

It’s become clear there is a role for Lazar in the post-deadline bullpen, although he’d bump down the depth chart. The Phillies are carrying three other rookies — Daniel Robert, Seth Johnson and Alan Rangel — who have pitched in lopsided or losing situations. The bullpen construction is flexible, even when factoring in the eventual August additions of David Robertson and José Alvarado.

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Robertson, who pitched over the weekend at Triple-A Lehigh Valley, is still on track to join the Phillies on Aug. 5. His fastball was 91-92 mph in that initial outing, a tick better than what the Phillies saw during his showcase for scouts. He averaged 93 mph last season while throwing a career-high 72 innings for Texas.

(Photo of Luis Robert Jr. making a catch in the fourth inning: Justin Casterline / Getty Images)

The Philadelphia Phillies continue a three-game series against the Chicago White Sox on July 29 at Rate Field in Chicago.

What time do the Phillies play today?

The Phillies face the White Sox at 7:40 p.m. on July 29. Left-hander Jesus Luzardo (8-5, 4.58 ERA) will pitch for the Phillies. Right-hander Jonathan Cannon (4-7, 4.48 ERA) will pitch for the White Sox.

What channel is the Phillies game on tonight?

The game will be broadcast on NBCSP. The radio broadcast will be on 94WIP and WDEL 101.7 FM/1150 AM.

Expert MLB daily picks: Unique MLB betting insights only at USA TODAY

How can I livestream the Phillies’ game?

If you live in the Philadelphia television market, NBCSP will stream the game on nbcsportsphiladelphia.com and the NBCSP app. NBCSP is also available on FuboTV, Hulu, Peacock and YouTube TV.

The game will also be available on MLB.TV to those with streaming packages. You can also stream the radio broadcasts with MLB Audio.

How can I watch the Phillies on Apple TV+?

The Phillies will be on Apple TV+ this season, but you’ll need a subscription if you want to watch it. A monthly subscription to Apple TV+ is $9.99. However, Apple TV+ offers a free trial with the requirement of an email or Apple ID.

Here is the remaining date the Phillies will be on Apple TV+.

The Philadelphia Phillies and Chicago White Sox meet Tuesday in MLB action at Rate Field. Here’s a Philadelphia Phillies vs Chicago White Sox Prediction. This article will include a Philadelphia Phillies vs Chicago White Sox Pick.

Philadelphia Phillies Betting Preview

The Philadelphia Phillies are 60-46 on the year and play the Tigers, Orioles, and Rangers next. The Philadelphia Phillies are batting .254 on the season, have a .328 OBP, and a .411 slugging percentage. The Philadelphia Phillies pitching staff has a 3.76 ERA and a 1.26 WHIP. Trea Turner leads the Philadelphia Phillies with 125 hits and 44 RBI, while Nick Castellanos and Kyle Schwarber have combined for 206 hits and 141 RBI.

Jesus Luzardo gets the ball for the Philadelphia Phillies, and he is 8-5 with a 4.58 ERA and 136 strikeouts this season. This will be Luzardo’s first career game against the Chicago White Sox.

Chicago White Sox Betting Preview

The Chicago White Sox are 39-68 on the year and play the Angels, Mariners, and Guardians next. The Chicago White Sox are batting .227 on the season, have a .299 OBP, and a .361 slugging percentage. The Chicago White Sox pitching staff has a 4.08 ERA and a 1.38 WHIP. Lenyn Sosa leads the Chicago White Sox with 87 hits and 38 RBI while Miguel Vargas and Chase Meidroth have combined for 164 hits and 56 RBI.

Jonathan Cannon gets the ball for the Chicago White Sox, and he is 4-7 with a 4.48 ERA and 72 strikeouts this season. This will be Cannon’s first career game against the Philadelphia Phillies.

Why the Chicago White Sox will win

The White Sox have won each of their last three games as home underdogs against NL East opponents.

The Phillies have lost three of their last four games as favorites.

The White Sox have covered the run line in 10 of their last 11 games as underdogs.

The Phillies have failed to cover the run line in four of their last five games against American League opponents that held a losing record.

The White Sox have led after 5 innings in three of their last four home night games.

Why the Philadelphia Phillies will win

The White Sox have lost 20 of their last 22 night games against National League opponents that held a winning record.

The Phillies have won eight of their last 10 night games against American League opponents following a loss.

The White Sox have failed to cover the run line in seven of their last eight games against NL East opponents following a home win.

The Phillies have covered the run line in each of their last seven Tuesday night games against American League opponents.

The White Sox have trailed after 5 innings in three of their last four home games against NL East opponents that held a winning record.

Chicago White Sox Player Prop Facts

Mike Tauchman has hit a home run in three of the White Sox’s last five games against NL opponents.

Josh Rojas has recorded a hit in each of his last seven appearances in night games against NL East teams that held a winning record.

Michael A. Taylor has recorded a Double in five of his last six appearances against NL opponents.

Philadelphia Phillies Player Prop Facts

Kyle Schwarber has hit a home run in three of the Phillies’ last four night games against AL opponents that held a losing record.

Jesus Luzardo has recorded seven strikeouts in five of his last six appearances.

Bryce Harper has recorded at least one Double in each of the Phillies’ last three night games against AL Central opponents that held a losing record.

Alec Bohm has recorded at least one hit in 22 of his last 23 appearances in night games against teams that held a losing record.

Kyle Schwarber ranks T4th in the league in Home Runs (36) this season.

Philadelphia Phillies vs Chicago White Sox Prediction

I’ve faded the White Sox for years, but they’re playing great ball in the second half and are making bettors money hand over fist over the last two weeks. The Phillies are comfortably the better team and Luzardo has above-average stuff, but he’s allowed 18 hits and 15 earned runs in his last 18.2 innings. Cannon has been up and down this season, but the White Sox have won each of his last five starts. I don’t do it often, but I have to give the White Sox the edge in this spot.

Philadelphia (60-46) vs Chicago (39-68) July 29, 2025 at 07:40 PM EDT The Line: Betting Odds: Chicago +1.5 — Over/Under: +8.5 (Get latest betting odds)

Randy Chambers’s Pick: Chicago White Sox

The Cleveland Guardians appear to be sellers ahead of this week’s trade deadline. However, their plans to reshape the roster for next season took a hit Monday when Emmanuel Clase was placed on non-disciplinary paid leave through Aug. 31 as part of MLB’s investigation into sports gambling.

On Monday, former MLB general manager Jim Bowden appeared on “Foul Territory” and said the Philadelphia Phillies had been exploring ways to strengthen their World Series chances by targeting both a reliever and an outfielder from the Guardians before Clase was placed on paid leave.

“We covered and watched Dave Dombrowski win a World Championship with the Florida Marlins and the Boston Red Sox,” Bowden said. “We saw him get the Tigers there, the Phillies there.

“But he really wants to get that World Championship ring with the Phillies. I feel like this is the year that he’s going to absolutely put that accelerator at full blast, get that back-end reliever that he wants. I believe he was in on Clase and [Steven] Kwan.”

“I believe he was in on Clase and Kwan.”@JimBowdenGM feels like this is the year Dave Dombrowski hits the accelerator at full blast. pic.twitter.com/TTCisxAWKo — Foul Territory (@FoulTerritoryTV) July 28, 2025

While the Phillies had their opportunity for a double swoop taken away due to an off-the-field issue, Bowden notes that Philadelphia will turn to other teams in the AL Central.

MORE: How Emmanuel Clase Paid Leave Sets Back Guardians’ Future, per Former MLB GM

“I thought there was a chance he gets both of them. I won’t be surprised, though, if he’s the guy that ends up with [Jhoan] Duran, and he’s the guy that ends up with Louis Robert [Jr.]. That wouldn’t surprise me at all.”

It’ll be interesting to see if the Phillies end up making any deals with the Guardians’ AL Central rivals — and whether the prospects involved eventually become quality major leaguers who might’ve been on Cleveland’s roster if the Clase situation hadn’t happened.