The Chicago Cubs enter Thursday on a nine-game losing streak. Entering the final two weeks of June, the Cubs are fourth in the division, only a half-game ahead of the Reds. It was unlikely that the team would compete for a playoff spot in 2022, but the start to the season and the possibility the Cubs might finish with one of the worst records in baseball is disappointing.

Last summer saw a difficult trade deadline where most of the key players from the 2016 World Series team were traded. The next few weeks will likely be similar to last year, with Jed Hoyer and the front office again trading away multiple players.

The Best Potential Trade Partners for Willson Contreras

Willson Contreras has been one of the best catchers in baseball during his time as a Chicago Cub. However, the 30-year-old is in the last year of his contract, and there has been no major news or progress on a contract extension.

As a result, Contreras will almost certainly be traded in the next couple of weeks and finds himself in the same position Kris Bryant, Javier Baez, and Anthony Rizzo were at this time last season. The only question remaining is which team the Cubs will trade Contreras to.

The Mets seem like the perfect fit. The franchise has been looking for improved offense at the position, with Tomas Nido recording an OPS of .536 so far this season and James McCann dealing with an injury. New York’s top prospect, and the No.7 prospect overall, Francisco Alvarez is a catcher, which means Contreras’ expiring contract status probably wouldn’t be an issue.

One obstacle to a trade may be last season’s Javier Baez trade between the Mets and Cubs. Pete Crow-Armstrong, the prospect the Cubs got in return for Baez, has already been promoted from Myrtle Beach to High-A South Bend this season and has become a Top 100 prospect.

Last year’s deal may discourage a similar trade this summer, but the Mets are a team determined to do everything they can to win this season after signing Max Scherzer, Mark Canha, and Starling Marte, along with trading for Chris Bassitt.

Interestingly, one of the other logical trade partners in a potential Contreras deal is another team the Cubs made a trade with last summer, the San Francisco Giants. The retirement of Buster Posey left last season’s NL West Champions looking to Joey Bart, a former top prospect, to be their primary catcher. Unfortunately, things haven’t gone as expected for Bart or the Giants, with the catcher being sent down to the minors earlier this month.

As a result, the Giants will be looking at finding improved production at the position this trade deadline, as it is possibly the area they could improve the most in the second half of the season. San Francisco has a deep and talented minor league system which could result in another trade deadline deal between the Cubs and the Giants.

In the American League, the Tampa Bay Rays could be a potential fit for Contreras. The Rays are caught in the toughest division in baseball this season and need offensive help after a series of injuries have affected the roster. At catcher, Mike Zunino is currently injured, and Francisco Mejia is at his best in a platoon role.

The Rays have one of the best farm systems in the entire MLB, which would help the two teams work out a trade. In addition, Contreras would add a veteran presence with extensive playoff experience behind the plate to help out a young pitching staff.

No matter where Contreras is traded it will represent the end of an era in Chicago. After the trade deadline, almost the entire roster from the 2016 World Series team will have moved on from their time with the Cubs.

Trading Ian Happ

Outside of Contreras, there are some other obvious trade candidates; David Robertson, Wade Miley, Drew Smyly, and several other players on expiring contracts are likely to leave Chicago. One player that could also be traded is Ian Happ.

Happ isn’t a free agent until after 2023, and his performance to start 2022 has been incredible. The left fielder is having the best season of his career and has shown dramatic improvement in drawing walks and avoiding strikeouts. Most notably, Happ appears to have taken a dramatic developmental step forward with his right-handed swing to add to his already excellent production from his left-handed swing.

As a result, trading Happ has entered the discussion in recent weeks. Happ will have just turned 29 when he becomes a free agent in 2023 and could be a perfect candidate for an extension. However, with the Cubs rebuild looking like an increasingly long-term project it is possible that Happ’s prime years of his MLB career won’t overlap with the Cubs’ next opportunity to contend.

This presents a dilemma for the front office. If Jed Hoyer and Carter Hawkins feel that their timeline to rebuild into a contending roster doesn’t overlap with Happ’s best seasons, then they should trade Happ this summer to maximize a potential trade return. The issue is that trading Happ would dramatically decrease the odds of the Cubs contending next season, or the year after if an agreement on an extension could be reached.

As a result, if Happ is traded this summer it will likely show that the Cubs’ leadership thinks it is unlikely that the team will compete for a playoff spot next year. While Hoyer and Tom Ricketts have been adamant that the Cubs are not in a rebuild, an Ian Happ trade would make it hard to believe the franchise isn’t in a long-term rebuilding project.