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  • Writer's pictureJack Vita

Who will the Chicago Cubs trade at the 2022 MLB trade deadline?

One year removed from a trade deadline massacre that fans on the north side are still recovering from, the Cubs are just two weeks away from likely shipping away even more talent.

Willson Contreras, Ian Happ, Kyle Hendricks, Marcus Stroman and David Robertson are among the club's biggest names that have had their names floated in trade rumors. So who will stay, and who will go? Before answering that pressing question, it's important to be realistic and understand just where the Cubs are at. The Cubs are 35-57, a half game better than the basement-dwelling Cincinnati Reds, in the MLB division with the worst cumulative winning percentage. Prior to winning on Sunday, they had lost 9 straight. The club dropped 10 straight a month earlier. Even playing in the worst division in the National League and perhaps the worst division in baseball, the Cubs have failed to capitalize and pile up wins.

Though the Cubs have a handful of promising young players already at the big league level such as Nico Hoerner, Seiya Suzuki, Christopher Morel and Keegan Thompson, the future of the Cubs lies in their farm system. The Cubs have three outfielders on's top 100 prospects list, and it's highly unlikely that any of them will reach the big league level this season. Brennen Davis (no. 28) hasn't played in nearly three months and is recovering from back surgery. Pete Crow-Armstrong (no. 77) and Kevin Alcántara (no. 96), who the Cubs acquired for Javier Baez and Anthony Rizzo last year respectively, have each climbed into's top 100, but both are currently in A ball, and it's unlikely either reaches the majors until 2024 at the earliest. The Cubs' other top 100 prospect, shortstop Cristian Hernandez (no. 67) is still in rookie ball and is on track for a 2025 debut.

A major league executive texted me earlier this week saying that, "The reason that the Cubs couldn't sustain their success is because there wasn't enough coming up through their farm system."

Last year's trade deadline began the process of reloading their farm system, and I expect to see the next stages of Extreme Makeover: Cubs Edition over the next two weeks.

Even when they had Kris Bryant, Anthony Rizzo, Javier Baez, Kyle Schwarber and others, the Cubs were stuck. The Cubs had a top three highest payroll in the National League from 2018 through 2020, and won zero playoff games during that stretch. Last year they bottomed out, and after failing to extend Baez, Bryant and Rizzo, the Cubs kicked off their rebuild, shipping away each player and adding a pile of prospects in their place.

Both Baez and Rizzo ended up settling for less money than the Cubs offered to them in extensions. Buster Olney reported that the Cubs offered Baez an extension "somewhere in the range of $180 million" prior to the start of the 2020 season. He signed for six years, $140 million last winter, losing out on $40 million. After his poor first half, Jon Heyman dubbed him the "Least Valuable Player" in his 2022 mid-season awards selections. Last spring, Rizzo rejected a 5-year, $70 million extension; he resigned with the Yankees this past winter for 2 years, $32 million, a $38 million loss. Meanwhile Bryant has played just 33 games this year, dealing with a back injury.

As they did ten years ago, the Cubs need to continue to build through their farm system. It's how they built a winner in 2016, and it's what needs to happen in order for the Cubs to once again raise the Commissioner's Trophy.

With one of the worst records in baseball, despite playing in arguably the sport's weakest division, I don't think the Cubs are close to competing. I think they're at least two more years away from being interesting. The team won't be competitive until 2024 at the earliest, and that's a best-case scenario.

So what happens in the meantime? The Cubs need to make decisions based around what will set their club up best for 2024 and beyond.

2022 is a lost season. The best thing the Cubs can do for the remainder of the summer is give young players regular repetitions and auditions for future roles. The Cubs have several interesting young pieces already at the big league level, and they need to figure out who is going to stick and be a part of the club's long-term plans.

As for position players, Nico Hoerner and Seiya Suzuki need to be playing everyday. Hoerner leads NL shortstops in Defensive Runs Saved (10) and is batting a team-best .307. In my opinion, he's been the Cubs' best and most consistent player in 2022, contributing on both ends, and on the base paths. Suzuki is one of the NL's best rookies, and with a great second half, could win Rookie of the Year.

Once Nick Madrigal returns from his groin strain, he should be the club's everyday second baseman. This would likely keep Morel in center field. If the Cubs plan to keep outfielder Nelson Velazquez at the big league level, I'd like to give him a chance to play everyday. This is where the Cubs should be kicking the tires to find out what they've got in players like him, Madrigal and Morel, while allowing for Suzuki and Hoerner to continue to develop. Chances are, not all of these guys are going to pan out and become cornerstone franchise players, but you need to identify which ones are. Which brings us to...

The Cubs should trade Ian Happ. If you want to sell high on a player, you have a prime opportunity to do so here. On August 11 of last season, he had a dismal slash line of .175/.284/.602 while playing minus-defense (-2 DRS).

The last two non-Covid seasons weren't pretty for him either. He slashed .233/.353/.761 in 2018, and after a poor showing at spring training, began the 2019 season in AAA, where he hit .242 through 99 games. Had it not been for a hot three-week stretch in September, Happ would have finished 2019 with an MLB slash line of .206/.297/.710.

This year has been a different story. Happ turned in a first half that earned him his first all-star nod, and with a year and a half left of club control before hitting free agency, the Cubs are at a crossroads. They have to make a decision on whether they extend Happ, or trade him. Happ has stated that he'd like to be a "Cub for life", but well, so would I. Happ's having a career year, but is there really anything all that special about a left fielder slashing .274/.364/.808 with 9 home runs at his very best? I would think a Happ extension would be in the ballpark of what Chris Taylor got from the Dodgers' last offseason: four years, $60 million. Maybe a little more considering inflation. Taylor has more versatility and can play several positions, though. Happ struggles to read fly balls off the bat, takes unconventional routes to fly balls, is a defensive liability and is limited to just left field and DH.

Typically left field is a spot for a bigger bat. Furthermore, the Cubs have several promising outfielders coming up through their system. I can't see Happ being a key piece for a Cubs' championship team and he's prone to regression. There's little reason to extend him and inadvertently block a higher-ceiling outfielder.

With Major League Baseball expanding its postseason to now include 12 teams, this deadline is a seller's market. There are more playoff spots available, and teams in the middle are more incentivized to buy than they are to sell, which means in theory, there should be less options available at the deadline. With less teams selling, the Cubs could capitalize on a seller's market and further max out on a player's value.

Andrew Benintendi was unable to enter Canada last week for the Royals' series in Toronto last week due to his vaccination status. Benintendi was previously seen as the best available outfield option for teams at the deadline, but now AL teams will be hesitant to trade for him, as he might not be available for what could be pivotal games in a playoff series in Toronto. This makes Happ — assuming he is in fact vaccinated more desirable to teams in need of outfield help that aren't willing to spend big on Juan Soto.

As for other Cubs' outfielders, well, I think Jason Heyward's days are numbered. When he comes back from his DL stint, his playing time would come at the expense of Morel and Velazquez. Heyward could take a bench role if he wants to stay in Chicago, but I'd imagine he'd rather get a chance to play regularly on another team, or play the role of fourth outfielder on a contending team. Heyward is owed another $22 million next year, the last of his eight-year contract. I don't think he's tradeable. The Cubs could package his contract along with one of the team's more desirable pieces, but then they wouldn't be able to pick up a nice prospect package. Whether the Cubs pay Heyward $22 million next year or not, isn't going to have a dramatic impact on their payroll or roster construction. My prediction is that Heyward will be designated for assignment, clear waivers, and eventually get picked up by another team on the Cubs' dime. The Cubs will pay the remainder of his contract. A change of scenery could benefit him. He could add leadership to a contending team or he could get a chance to play on a non-contending team. If he were to bounce-back, that team could trade him at next year's deadline.

Willson Contreras feels like the 2022 version of Bryant, Rizzo and Baez. His contract is up at the end of the season, and he and the Cubs haven't agreed to an extension. If the Cubs were keeping him, they'd have extended him by now.

Contreras will be entering his age-31 season and hoping to bank a deal similar to the one J.T. Realmuto received last winter with the Phillies (5 years/$155.5 million). Contreras doesn't fit the Cubs' timeline.

The Cubs probably should have have moved him at last year's deadline; he would have had more trade value at that time, with another year of club control. The Cubs probably hoped to resign him, but clearly don't value him the way Contreras and his agent do, otherwise an extension would have happened by now.

Though Contreras is a minus-glove and weak pitch-framer behind the plate, he could add a lot to a contender in need of a big bat. Contreras has played some outfield for the Cubs and I actually like him out there. He's athletic, reads fly balls well and has a great arm. So he could be an option for teams looking for a corner outfielder, too.

Last winter, executive Jed Hoyer once again did a nice job of adding veteran relievers he'll be able to flip at the deadline. Last year he cashed in on Ryan Tepera and Andrew Chafin, and this year he will likely do the same with David Robertson (1.93 ERA), Mychal Givens (2.92) and Scott Effross (2.93). No team can ever have too many quality relievers in their arm barn. I'd expect each of those three dealt by the deadline.

As for starting pitching, Kyle Hendricks and Marcus Stroman could really go either way. Hendricks is having a down year and Stroman just got back from a shoulder injury, but the starting pitching market is rather thin past Luis Castillo and Frankie Montas. Teams like the Cardinals that are in dire need of starting pitching could be in play for either Hendricks or Stroman. Both guys are under contract through 2024, so the Cubs don't have to trade either now. Perhaps both guys pitch better next year and the Cubs can sell higher on them then (which is what I think happens). It will depend on what the trade market looks like, and what kind of offers the Cubs receive. With Hendricks on the DL and not throwing, a trade involving him seems rather unlikely. Stroman just came back from a shoulder injury and has struggled to pitch deep into games, so my gut says he stays for now.

Drew Smyly is on a one year contract, so if a club calls wanting a fourth or fifth-starter, he's gone. Moving Smyly would make room for prospect Caleb Kilian to join the rotation for the remainder of the season, once scouts deem him ready.

The only other significant player that could get moved is Patrick Wisdom. Wisdom is a power bat (17 home runs) and quality defender. He'd add value to a contending team, but I don't think the return on him would be anything significant. The Cubs don't have many other options to play third base at this time either. Besides, somebody has to be in the Carshield commercials! I think he stays.

Perhaps other players, like Rafael Ortega and Yan Gomes, are throw-ins in other trades, but that's about it.

In the second half, at its healthiest, I think the most common Cubs' lineup and pitching rotation you'll see will look like: C P.J. Higgins

1B Alfonso Rivas

2B Nick Madrigal

SS Nico Hoerner

3B Patrick Wisdom

LF Nelson Velazquez

CF Christopher Morel

RF Seiya Suzuki

DH Frank Schwindel

SP Kyle Hendricks

SP Marcus Stroman

SP Keegan Thompson

SP Justin Steele

SP Caleb Kilian

For more MLB analysis, catch the latest episode of the Jack Vita Show, where Jack talks MLB All-Star snubs, Home Run Derby, Mid-Season awards, first-half surprises and disappointments, and bold predictions for the second half with Tabitha Bingham!

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For more sports and entertainment analysis, follow me on Twitter @JackVitaShow, and subscribe to the Jack Vita Show on iTunes or wherever podcasts are found. You can also find me on Facebook and Instagram.

(Image via Armando L. Sanchez/Chicago Tribune)


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