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Matt Shaw trade destinations: Where Cubs should look for a starting pitching upgrade

With Chicago in need of healthier arms, their former top prospect becomes an invaluable trade chip.
Matt Shaw - Chicago Cubs
Matt Shaw - Chicago Cubs | Raymond Carlin III-Imagn Images

Key Points

Bullet point summary by AI

  • The Cubs need pitching depth with multiple starters on the IL and rehabbing from surgery.
  • Trading Matt Shaw is seen as the easiest path to upgrading their rotation this season.
  • Several teams could offer valuable pitching returns, but each comes with different risks and timelines for impact.

After winning 10 straight between late April and early May, the Chicago Cubs have hit a skid, dropping three straight series against Texas, Atlanta and the crosstown White Sox, losing six of their last nine games.

Cubs fans needn't panic, but it is clear Jed Hoyer and the front office have work to do to round out a World Series-caliber roster. That starts with the pitching staff. Matthew Boyd and Cade Horton are both on the IL, while Justin Steele is still rehabbing from elbow surgery. The Cubs' easiest path to a critical pitching upgrade is probably trading Matt Shaw, their former No. 1 prospect who is currently blocked from the everyday lineup by Alex Bregman.

These teams could be interested in helping the Cubs out if Shaw is made available:

New York Yankees

Luis Gil - New York Yankees
Luis Gil - New York Yankees | David Butler II-Imagn Images

Ryan McMahon continues to strike out at an unsustainable rate, and New York could use more functional, full-time right-handed bats. Anthony Volpe is stuck in a downward spiral at shortstop, while Amed Rosario and Max Schuemann — despite their early-season production — are not viewed as long-term investments. Jazz Chisholm Jr. is also an upcoming free agent, lest we forget.

There's a path for Shaw to play early and often in New York while hopefully developing into the next cornerstone of their infield. The Yankees are snakebitten on the injury front right now, not unlike Chicago, but there are plenty of depth options to work into a trade. Carlos Lagrange, New York's No. 4 prospect per MLB Pipeline, has unicorn velocity and major upside. He'd probably be the ideal return piece.

In reality, the Cubs are probably looking at a mix of Luis Gil and/or Chase Hampton, the latter of whom is on New York's 40-man roster but in the final stages of Tommy John recovery. Carlos Rodón profiles as a potentially interesting buy-low candidate after a rough start, but his contract probably precludes him from Shaw talks specifically.

Pittsburgh Pirates

Mitch Keller - Pittsburgh Pirates
Mitch Keller - Pittsburgh Pirates | Justin Berl-Imagn Images

If the Cubs are willing to trade Shaw within the division, Pittsburgh has the right mix of pitching depth and offensive need to strike up a conversation. Veteran workhorse Mitch Keller has been a staple in trade rumors for a couple years now, while minor-league arms like Hunter Barco, Antwone Kelly and Thomas Harrington could all hold appeal for New York as developmental bets.

Pittsburgh does not offer Shaw the most immediate path to everyday reps, but unlike Chicago, there is not a years-long bar at every major infield (or outfield) position. Brandon Lowe was a rental and there's no guarantee Pittsburgh can afford to re-sign him. Nick Gonzales, meanwhile, is producing well above expectations, but he won't maintain his current sky-high contact rate.

Shaw can fill holes across the positional spectrum, much like he is currently in Chicago, with hopes of breaking through as a regular at second or third base in 2027.

Tampa Bay Rays

Nick Martinez - Tampa Bay Rays
Nick Martinez - Tampa Bay Rays | Philip G. Pavely-Imagn Images

Very few teams manage assets on the margins more successfully than Tampa Bay. The Rays win seemingly every trade and know exactly how to extract maximum value from a situation, whether it's buying low or selling high, all while spending considerably less money than the bulk of their opponents.

Tampa is red-hot right now, with the best record in the American League. The Rays are loaded with solid, fundamental hitters and a deep reserve of quality pitchers. Their rotation has already survived multiple early-season injuries, not skipping a beat with both Ryan Pepiot and Steven Matz on the IL.

Nick Martinez has a plainly unsustainable 1.51 ERA through nine starts. Tampa would be wise to sell high once the rotation approaches full strength. Chicago is probably aiming higher than a 35-year-old rental when it comes to a potential Shaw trade, however, so it could take a prospect or two on Tampa's end to grease the wheels. Or, we could see the Cubs aim higher for a Pepiot or even a Shane McClanahan, with the latter due for free agency in less than two years.

Boston Red Sox

Jake Bennett - Boston Red Sox
Jake Bennett - Boston Red Sox | Brian Fluharty-Imagn Images

Boston still has a stockpile of intriguing arms, despite trading several quality pitchers in the offseason and dealing with an early onslaught of injuries. Unfortunately, the Red Sox are not on a winning path currently, which could mean Craig Breslow is more open to shaking things up and further trading from their pitching reservoir, even if it leaves Boston compromised in the short term.

And, make no mistake, the Red Sox also need righty bats, with third base in particular shaping up as their foremost position of need. Caleb Durbin has a .491 OPS and is one of the worst qualified hitters in MLB right now. That trade (and the decision to not re-sign Alex Bregman) has aged poorly thus far. It would be ironic, but not unreasonable, for their long-term Bregman replacement to be the up-and-comer whom Bregman replaced in Chicago.

Jake Bennett, a 25-year-old lefty, has already made his major-league debut this season amid Boston's injury spiral. He was acquired in a straight prospect swap in the offseason and could help the Cubs sooner than later. Tyler Uberstine, another talented pitching prospect, is also on the MLB doorstep.

If the Cubs want to aim higher, Sonny Gray is sure to be available, and even asking about Ranger Suárez wouldn't be the craziest thing in the world, although his long-term deal probably keeps him tethered to the Red Sox for a while, regardless of how this season plays out.

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