As the trade deadline nears Jed Hoyer faces new harsh reality

The MLB trade deadline is on August 3rd at 6 pm EST. The Chicago Cubs find themselves in a very tough spot. Many Cubs fans still remember how President of Baseball Operations Jed Hoyer did not go all-in during last year’s trade deadline. How can anyone forget Hoyer acquired lower-cost depth pieces. These included reliever Andrew Kittredge, starter Michael Soroka, lefty reliever Taylor Rogers, and utility man Willi Castro. Players felt the front office’s caution. As a result, the team’s momentum stalled.

As the Cubs are in the Wild Card race again this season, their needs are obvious: pitching, pitching, and more pitching. However, the market has changed dramatically in recent weeks.

The Boston Red Sox recently ripped off 15 straight wins, tying the franchise record. They have vaulted themselves into playoff contention. Starter Sonny Gray? Off the table. Closer Aroldis Chapman, a former Cub who won the World Series with them in 2016? Off the table. Boston does not look like a seller anymore.

That alone shrinks the pitching market. But the Cubs’ challenge doesn’t end there.

Across town, the Chicago White Sox — improbably leading the AL Central — also need pitching as the Cubs do. If both Chicago teams are bidding on the same pitchers, the Cubs are not in a favorable position. While they have indicated they are not going to deal their top 10 prospects, their system still has more high-end talent and still can offer better prospect packages than the Cubs.

What if the Cubs were outbid for the same pitcher the White Sox were after? That will not sit well with many Cubs fans.

After another poor outing by Jamison Taillon against the Pittsburgh Pirates on Sunday, manager Craig Counsell has indicated his spot in the rotation might be in serious jeopardy. Counsell may have finally run out of patience with Taillon. Notably, Javier Assad, who pitched three shutout innings on Saturday to earn his first career save, could replace Taillon in the rotation. But outside reinforcements are still needed.

If he lands impact pitching, he can galvanize the Cubs in their hopes of making a deep playoff run. If he settles for marginal moves again while waiting for pitchers who are on the IL to return, the Cubs are risking another early playoff exit as well as destroying the morale inside the clubhouse again.

Every executive has a moment where his reputation and philosophy are being put to the test. For Jed Hoyer, judgment day is on August 3rd. With a potential lockout looming next season, and so many veteran players expected to become free agents after this season, the stakes are very high.

With fans’ patience running thin and the deadline coming fast, Hoyer can cement both his reputation and legacy in the upcoming trade deadline.

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