Cubs’ worst trade fears might be saved by an unlikely ex-crosstown rival

Chicago's ambitious deadline plans are a double-edged sword — one that an unlikely trade candidate could save them from.
May 27, 2025; Chicago, Illinois, USA; Chicago Cubs players complete a mound visit with pitcher Chris Flexen (77) during the eleventh inning against the Colorado Rockies at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images
May 27, 2025; Chicago, Illinois, USA; Chicago Cubs players complete a mound visit with pitcher Chris Flexen (77) during the eleventh inning against the Colorado Rockies at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images | Patrick Gorski-Imagn Images

The Chicago Cubs are known to be scouring the market for pitching help ahead of the July 31 trade deadline. With Jameson Taillon now joining Justin Steele and Javier Assad on the IL, the pressure to find a stable rotation arm is mounting. The Cubs need someone other than Matthew Boyd and Shōta Imanaga who can be trusted in the playoffs.

While a trade feels like the obvious (and perhaps likely) solution, the Cubs need to tread carefully. This is a team with a notoriously cheap front office relative to their market size. Chicago cannot afford to splurge on pricey target targets without the intent of keeping them long-term. That is especially true given Kyle Tucker's impending free agency. The Cubs are about to commit all their financial resources to trying to re-sign Tucker, and there's a good chance they won't succeed. If Chicago takes a step back next season without Tucker, they will come to regret mortgaging significant assets for a pitching rental.

So how about the in-house solution? The Cubs should explore the trade market, but odds are Chicago can't — or won't — add a true ace with postseason bonafides. They will need someone to step up internally as well. Look no further than Chris Flexen, a former rival from the South Side.

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.

Cubs can stretch Chris Flexen to starter as pitching woes mount

Flexen spent last season with the Chicago White Sox, starting in 30 of 33 appearances and logging a 4.95 ERA across 160.0 innings. That number is slightly inflated relative to Flexen's career ERA of 4.76 and it's hard to hold him 100 percent accountable when the clubhouse around him was such a dumpster fire. Before stints with Colorado and Chicago (x2), Flexen put a couple of strong seasons together with the Seattle Mariners in 2021 and '22 (3.66 ERA, 317.1 IP, 220 K in 64 games).

Now we are seeing Flexen get back to his winning ways. He is 5-0 through 16 appearances and 29.0 innings out of the bullpen this season, with a 0.62 ERA and 0.83 WHIP. Pound for pound, very few relievers have operated at Flexen's level this season. It's not the largest sample size for the most high-leverage of roles, but the 31-year-old is generating tons of soft contact. He has been a bit lucky per Baseball Savant, but even Flexen's expected ERA of 2.98 is among the best in baseball.

Projected Cubs rotation with Chris Flexen as a starter

Flexen is "a candidate to be stretched out as a starter," per Patrick Mooney of The Athletic. So this is very possibly happening. Chicago only has six games left until the All-Star break, so it's a sprint — or a slow, injury-hampered crawl — the the finish line. Or in this case, a few days off. Matthew Boyd might be in the All-Star game, but the rest of Chicago's staff should get the added days of rest, while the front office can take its time evaluating potential trade options.

In the meantime, here's generally how the rotation would shape up with Flexen in Taillon's place.

Order

Name

1

Matthew Boyd

2

Shōta Imanaga

3

Cade Horton

4

Colin Rea

5

Chris Flexen

This feels like a simple, effective solution to a long-gestating problem in Chicago. The Taillon injury certainly exacerbates things, but we've known the Cubs need another impact arm for months now. Perhaps the answer to the question of 'who?' has been staring them in the face this whole time.