3 Jed Hoyer trade deadline regrets that will cost Cubs in October

The Chicago Cubs needed to swing big at the trade deadline. Kyle Tucker’s contract expires after the season, which means this could very be a one-and-done situation. Genuine opportunities to win the World Series are rare and the Cubs are a big-market franchise with plenty of cash. It’s a shame that ownership and the front office don’t always seem willing to spend it.

Rather than a big swing, the front office took more of a metaphorical bunt. Jed Hoyer, fresh off of signing an extension as president of baseball operations, swung three noteworthy trades, acquiring RHP Michael Soroka from Washington, LHP Taylor Rogers from Pittsburgh and UTL Willi Castro from Minnesota.

Castro helps them at third base and gives Chicago a utility glove to move around the diamond. Fine. Rogers is a solid bullpen arm enjoying his best season to date. Good! Soroka is, well… he starts on the mound every fifth day. That’s something the Cubs need. Fans are just left wanting more.

Here are a few mistakes Hoyer won’t be able to live down if Chicago flames out in October.

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3. Cubs missed on the truly elite relievers like Jhoan Durán and Mason Miller

Chicago definitely strengthened its bullpen with the Taylor Rogers trade and the subsequent Ryan Pressly DFA, but the Cubs’ bullpen has been one of their greatest weaknesses ever since Craig Counsell’s arrival. Daniel Palencia has taken well to the closing role this season, but Chicago could’ve used another lights-out option to finish games.

Jhoan Durán and Mason Miller are two of the very best closers in the sport, both with multiple years left on their contracts. And both were moved at the deadline. It seems like Durán was probably a more realistic target — I’m not sure we can condone San Diego trading the No. 3 prospect in all of baseball for a closer — but the Cubs have a deep farm system and a reason to go all-in. Either Durán or Miller would have meaningfully improved their chances.

Even if the Cubs didn’t want to pay top dollar, other great closers, such as Ryan Helsley, Shelby Miller (who went to division leader Milwaukee) and Camilo Doval were all traded on Thursday. Just getting one more high-leverage arm in addition to Rogers would’ve made fans a lot happier.

2. Cubs needed to capitalize on the starting pitching market

With all due respect to Michael Soroka, he hasn’t been on a very promising trajectory these last five years. He just became the worst starter in a weak rotation, which stands out as Chicago’s foremost concern moving toward October. Matthew Boyd and Shōta Imanaga are All-Stars, but how well the Cubs’ depth holds up beyond them remains to be seen.

Chicago is sure to scour the free agent and waiver markets in the coming weeks, while internal promotions are always a possibility, but a lot of quality starting pitchers heard their names pop up in trade rumors. Even if the Cubs couldn’t land a controllable talent like Sandy Alcántara or Edward Cabrera in Miami, we saw several top-notch rentals — Merrill Kelly, Charlie Morton, Shane Bieber — change teams. Other more prominent names, like Zac Gallen or Dylan Cease, could’ve been had for the right price.

This Cubs farm system is deep and the pressure is on right now. Soroka is not a starter once the playoffs roll around. Hell, if his production doesn’t improve, but might not even be on the postseason roster. Chicago not doing better on this front in particular was easily the most inexplicable and egregious of Hoyer’s deadline fumbles.

1. Cubs will come to regret Eugenio Suárez whiff

This applies to several contenders, but Eugenio Suárez was a dream target for the Cubs. It’s not hard to understand why this didn’t happen — Jed Hoyer is practical to a fault and Suárez, like Kyle Tucker, hits free agency in a few months — but Chicago should be throwing caution to the wind. Suárez has been one of the best hitters in the National League this season, posting a .248 average with an .895 OPS and 36 home runs.

Instead, he goes to the Seattle Mariners, a smaller-market club with even less hope of re-signing Suárez next winter. His 143 wRC+ is the second-highest on Seattle’s roster, trailing only MVP frontrunner Cal Raleigh (167 wRC+). Suddenly, the M’s feel like a real threat to win the American League. The Cubs, meanwhile, are sliding down the NL power rankings after active deadlines from San Diego, New York, Philadelphia and others.

The biggest weak point in Chicago’s lineup all season has been third base. Former top prospect Matt Shaw has found his groove in recent weeks, but he’s sitting at a .644 OPS with six home runs in 246 at-bats. Willi Castro should help at the hot corner, but replacing a below-average bat with one of the very best power swings in MLB would’ve put the Cubs much closer to that elusive World Series.

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