The Best & Worst Trades at the MLB Trade Deadline in Cubs History

The Best & Worst Trades at the MLB Trade Deadline in Cubs History

The 2022 MLB Trade Deadline is Tuesday, and the Illinois sports betting marketplace clearly expects the 41-60 Chicago Cubs to be sellers this year. 

The club is almost 16 games behind the division leading Milwaukee Brewers and well out of playoff contention. Illinois betting apps have clearly taken notice of the Cubs poor outlook for the rest of the season, as they are tied for last on the World Series odds board at DraftKings Sportsbook and can be found at +80000 to stage a miracle finish and win the National League Central Division.

Just as they were last year, the main trade pieces for the Cubs are a trio of relievers, with David Robertson and Mychal Givens on the block and likely to join Chris Martin as ex-Chicago Cubs after Martin was traded to the Los Angeles Dodgers on Saturday. 

As sellers this year, it will take a few years to tell if any of the trades they make this deadline pay dividends or make management look foolish.

Chicago is a team with a storied past, both in good ways and bad, and its trade history also tells the same tale.

In recent years, the Cubs best trades are the ones that shaped the 2016 World Series championship squad.

Acquiring Aroldis Chapman from the New York Yankees around the deadline that summer was a huge move, as the closer was a key member of their championship team. They acquired him at the deadline for a package of youth, including shortstop Gleyber Torres, who has predictably turned into an exceptional player for the Yankees. 

Despite this, the Cubs would make the trade again in a heartbeat as it led to the aforementioned championship.

Another key trade that molded that championship roster was at the 2012 deadline, when the Cubs were in a selling position, similar to this year. 

They acquired Kyle Hendricks when the pitcher was still pitching in High-A ball, but in 2016 he ended up pitching the clinching game in the NLCS and started the clinching game of the World Series as well.

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Best Trade in Cubs MLB Trade Deadline History

July 2, 2013 Trade Total WAR of Acquisitions
⚾️ Cubs receive P Jake Arrieta & P Pedro Strop 27.0
⚾️ Orioles receive P Scott Feldman & C Steve Clevenger1.2

Best Cubs Deadline Trade Broken Down

While those trades were exceptional, the best deadline deal the Cubs have made has to be the acquisition of Jake Arrieta and Pedro Strop from the Baltimore Orioles for starter Scott Feldman and catcher Steve Clevenger in the summer of 2013. 

Arrieta could never get his game together in Baltimore, but he transformed into one of the best pitchers in the league in his time in Chicago, winning a Cy Young as well as the World Series with the Cubs. 

Not to be outdone, Strop turned into one of the best relievers in Cubs history and his 411 appearances with the team rank sixth all time. 

The Wins Above Replacement (WAR) value of this trade for the Cubs over the players' time with the team was 27.0, compared to a measly 1.2 WAR for Feldman and Clevenger in Baltimore. 

WAR is an analytical measure that compares players to the theoretical performance of the average replacement player in the same position. The website was utilized to find these statistics.

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Worst Trade in Cubs MLB Trade Deadline History

June 15, 1964 Trade Total WAR of Acquisitions
⚾️ Cubs receive P Ernie Broglio, P Bobby Shantz, OF Doug Clemens -1.1
⚾️ Cardinals receive OF Lou Brock, P Jack Spring, P Paul Toth42.8

A Look at the Brock for Broglio Deal

Not all trades turn out well, and Chicago certainly has been on the wrong side of them before, most infamously with the ‘Brock for Broglio’ swap in 1964. 

Lou Brock was traded from Chicago to St. Louis in July of that year in a three for three swap, with Ernie Broglio the main piece coming back. Broglio, who later was found to be hiding an elbow injury before the trade, had a 4.04 ERA in limited appearances with the Cubs and by 1966 was out of the league entirely. 

Brock was fantastic for the Cardinals, leading them to the World Series in 1964 and 1967 and becoming a no-doubt hall of famer. 

The total WAR acquired by St. Louis in this trade was 42.8, while Chicago actually got negative value from their end of the trade with a WAR of -1.1.

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Illinois Sportsbooks Expect Cubs To Be Sellers This Year

No trade can be graded immediately, especially for teams in the selling position of the 2022 Chicago Cubs. 

Over at BetMGM Illinois Sportsbook, the Cubs are a whopping +250000 to win the National League, odds that make it all but certain the team will shed talent in the coming days for future potential. 

After acquiring some decent futures pieces last year, the management team will be looking to find the next Kyle Hendricks or Jake Arrieta and hoping not to repeat the mistake of the 1964 deadline from years past.

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Cecil Peters
Senior Betting Analyst

Cecil Peters is a Senior Betting Analyst for A professional sports bettor in Canada, Cecil specializes in analyzing the latest odds impacting professional sports, particularly MLB and the NHL. He will be providing insight throughout the baseball season.

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