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3 Chicago Cubs trade scenarios to help expedite rebuild in the Windy City

Vincent Frank

Following Sunday’s win over the Philadelphia Phillies, the Chicago Cubs find themselves at 38-57 and completely out of the National League Playoff race.

It’s led to widespread speculation that front office head Jed Hoyer could sell off some veteran assets ahead of the Aug. 2 MLB trade deadline.

Stuck between a long-term rebuild and complete irrelevance, the Cubs must add to a farm system that ranks 18th in baseball right now. With a ton of valuable veteran players potentially on the market, Chicago must use the next several days to do just that. Below, we look at three Chicago Cubs trades to help expedite their rebuild.

Related: Updated MLB Playoff and World Series predictions

Chicago Cubs send multiple pitchers to Toronto Blue Jays

chicago cubs trade drew smyly to the toronto blue jays
Eric Hartline-USA TODAY Sports

Chicago has a trio of veteran pitchers who could be of interest to contending teams. Each one comes in pretty cheap. That includes veteran starter Drew Smyly and reliever Mychal Givens.

Smyly, 33, is currently playing under a one-year, $5.25 million contract. He’s also been a decent bottom-end of the rotation guy, pitching to a 4.22 ERA thus far this season. As for Givens, the veteran reliever has posted a 2.87 ERA while striking out 46 batters in 37.2 innings this season.

Looking to contend with the Tampa Bay Rays for second place in the American League East moving forward, Toronto needs to add depth to its pitching staff. Hyun Jin Ryu is out for the season. Fellow starter Yusei Kikuchi has joined him on the injured list. There’s also a need in the pen.

  • Chicago Cubs trade: Drew Smyly, Mychal Givens
  • Toronto Blue Jays trade: Hayden Juenger, Tanner Morris

Chicago can’t expect a ton in return for two mid-tier veteran rentals. Here, it dips into Toronto’s 21st-ranked farm system by adding two top-30 prospects in Juenger and Morris. Juenger, 21, is the most interesting of the two prospects in that he’s struck out 67 batters in 56 innings in 20 games (17) starts for Double-A New Hampshire while sporting a 4.02 ERA.

As for Morris, the infielder hit .345 in his final season at Virginia before the former fifth-round pick moved on to the minors. He hit .312 with an .898 OPS at Double-A before a promotion to Triple-A this season. Morris could be ready to take on a utility role as early as this summer.

Related: Chicago Cubs standing in our latest MLB power rankings

Cubs trade Ian Happ to the Houston Astros

chicago cubs trade ian happ to the houston astros
Jayne Kamin-Oncea-USA TODAY Sports

A first-time All-Star this season, Happ will be a highly sought-after option on the trade market should Chicago make him available. Defensively, he has the ability to play all three outfield positions. Happ has also seen time at second and third in his career. That type of flexibility can’t go unnoticed.

  • Ian Happ stats (2022): .280 average, 9 HR, 44 RBI, .811 OPS

While the 27-year-old Happ has seen his power numbers dip from a season ago, he’s still a darn good consistent bat. That’s something Houston will need if it is going to compete with the New York Yankees in the American League Playoffs.

Michael Brantley is currently on the injured list. Jose Siri (.178 average) and Chas McCormick (.230) have both struggled at the plate this season. Happ would be an obvious upgrade over the pair.

  • Chicago Cubs trade: Ian Happ
  • Houston Astros trade: Hunter Brown, Yainer Diaz

Per MLB.com, Houston boasts the second-worst farm system in baseball. In order for it to pull off a trade with the Chicago Cubs, giving up top prospect Hunter Brown would have to be in the cards. Brown, 22, was a fifth-round pick of the Astros back in 2019. He’s deen dominant in Triple-A Sugar Land this season — pitching to a 6-3 record with a 2.62 ERA and 1.15 WHIP while striking out 101 batters in 75.2 innings. Brown would immediately join the Cubs’ rotation.

As for Diaz, the 23-year-old is also currently at Triple-A. The Dominican native has played both corner outfield spots as well as first base and catcher in 57 games. He’s also hitting a robust .316 with nine homers, 48 RBI and a stellar .871 OPS.

Related: Updated MLB trade rumors heading into Aug. 2 deadline

Chicago Cubs trade Willson Contreras, veteran pitcher to the New York Mets

MLB: Boston Red Sox at Chicago Cubs
Quinn Harris-USA TODAY Sports

New York just pulled off a trade for a depth option at catcher. In no way does this mean the team doesn’t need a true upgrade over Tom├ís Nido. It’s not brain surgery. Considered one of the better catchers in the game, Contreras continues to perform well at the plate and behind the backstop.

Willson Contreras stats (2022): .258 average, 14 HR, 37 RBI, .844 OPS

Despite his status as a pending free agent, New York has the payroll to re-sign Contreras. He wouldn’t necessarily be a rental.

The Mets also add to their bullpen with a formerly dominant David Robertson who has returned to form in 2022. The veteran is pitching to a 1.88 ERA and 0.97 WHIP while striking out 49 batters in 38.1 innings.

  • Chicago Cubs trade: Willson Contreras, David Robertson
  • New York Mets trade: Dominic Hamel, Carlos Cortes, JT Schwartz, Carlos Rincon

In lieu of requesting one of the Mets’ top prospects, Chicago opts to go with depth here. That includes No. 9 prospect Dominic Hamel. He’s considered a four-pitch hurler who relies on an above-average fastball and slider. The former third-round pick has also performed well in lower-level ball this season, pitching to a 3.72 ERA while striking out 93 in 77.1 innings.

Cortez, 25, is a former third-round pick out of South Carolina. He’s struggled a bit since being promoted to Triple-A, but is one year removed from hitting 14 homers. Schwartz and Rincon add more depth with the former projcting as a first basemen and the latter potentially set for a cup of coffee in the majors after hitting 22 homers a season ago.