5 absolutely wild Chicago Cubs trade possibilities from Jim Bowden

Man, Jim Bowden ponders trade deadline possibilities and hot stove wheeling and dealing the same way I run a franchise on MLB The Show. No holds barred, anything goes. To say he didn’t disappoint in his latest piece is putting it mildly because there are some possibilities here that will undoubtedly make Chicago Cubs fans pull out their hair.

That’s not to say they’re all far-fetched, because there’s not. Some actually just reiterate reports we’ve heard for weeks on-end now. But without further ado, let’s just dive right in and talk through some of these scenarios Bowden speculated on in The Athletic (subscription required):

Chicago Cubs Rumors: A return to Boston for Craig Kimbrel and Anthony Rizzo

The Red Sox have surprised the baseball world, entering play Wednesday 19 games above .500 and in first place in the American League East. Manager Alex Cora has returned from his one-year suspension to emerge as a potential AL Manager of the Year finalist, but his team likely needs reinforcements if it’s to hold off the likes of Tampa Bay, Toronto and New York.

Enter Bowden’s first potential trade deadline move – one he described as a ‘dream’ scenario for the Red Sox: Chicago sending not only Craig Kimbrel to Boston, but also including Anthony Rizzo, in a homecoming of sorts for the two players.

Of course, the Sox initially drafted Rizzo in the sixth round way back in 2007. That started the career-long relationship between the three-time All-Star and Theo Epstein and Jed Hoyer that wound up with his arrival in the Windy City and a World Series championship. Boston has a glaring need at first and Rizzo brings not only Gold Glove-caliber defense, but a winning pedigree and postseason experience.

Kimbrel spent from 2016 to 2018 with the Red Sox, playing a key role in the team’s 2018 World Series title, notching 42 saves before foraying into free agency, where he wound up signing with the Cubs halfway through the 2019 campaign. Adding a future Hall of Fame closer certainly improves Boston’s chances come October – and there’s familiarity on both sides of the equation.

Chicago Cubs Rumors: Javier Baez joins Tim Anderson on the South Side

With Nick Madrigal sidelined for the rest of the year, the Chicago White Sox have a glaring hole at second base. This team looks like it’s on cruise control with October set in the GPS, but come October, such a weakness could prove costly.

What better way to quash the Tim Anderson-Javier Baez comparison than having them team up down the stretch with one united goal: bringing a World Series championship to the South Side.

I’m not here to tell you this is a wholly unrealistic proposal. The Sox still have some young talent that the Cubs might like to get their hands on and, if Chicago can’t work out a long-term extension with its shortstop ahead of July 30, you know Baez would love to stay in the Windy City – even if that might mean playing for the other team.

Whether or not he truly wants $200 million in his next deal, Baez undoubtedly has the potential to make his presence felt in a huge way. We saw that back in 2018, when he put the Cubs on his back en route to a runner-up finish in NL MVP voting.

This is one of those ideas that makes sense logically, but, like I said, will rub folks who love their Cubs the wrong way if for no other reason than because it involves the White Sox.

Chicago Cubs Rumors: Milwaukee Brewers pursue Kris Bryant or Anthony Rizzo

Boy, I mean, if you’re taking a swing, it might as well be a daddy hack.

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In recent years, the Brewers and Cubs have developed a pretty heated rivalry. For some time, it didn’t really mean all that much when they went head-to-head, but that’s all changed. Milwaukee came into Wrigley Field in 2018 and won Game 163 at Wrigley Field, sending Chicago to a prompt postseason exit at the hands of the Rockies in the Wild Card Game shortly thereafter.

Armed with a three-headed monster atop the rotation in Corbin Burnes, Brandon Woodruff and Freddy Peralta and a dynamic duo of Devin Williams and Josh Hader in the late innings, Milwaukee has the arms to make that deep postseason run. But it needs more offense – and that’s something Anthony Rizzo and Kris Bryant have experience delivering.

To be clear, Bowden doesn’t say the Brew Crew will go out and land both of these guys. He calls Bryant a ‘realistic target’ and says that both Boston and Milwaukee ‘make sense’ for Rizzo.

I’m not saying it won’t happen, but I am saying that Cubs ownership and the front office is running low on political capital with fans right now and trading any one of the two beloved Chicago superstars to a division rival would be the straw that breaks the camel’s back for a lot of folks.

Chicago Cubs Rumors: Yet more Cubs wind up heading to the Nationals

Seriously, if you have a favorite Cub from the last few years and aren’t sure where he’s playing now, there’s a good bet it’s Washington, D.C. Jon Lester, Kyle Schwarber and Starlin Castro all call D.C. home now – and they’re managed by Joe Maddon’s former bench coach, Dave Martinez.

The team’s historic 2019 World Series run was sparked by a second-half surge, so it’s hard for GM Mike Rizzo to ever fathom selling, regardless of his team’s place in the standings. Right now, the Nationals are four games under .500 and five games back in the NL East. As Cubs fans know full well after the last month, that’s hardly an insurmountable gap.

Bowden mentions two Cubs specifically who could fit in Washington. Of course, I don’t even need to tell you this first: Kris Bryant. Bryant makes so much sense for the Nats it’s not even funny. The other is Zach Davies who is very clearly not the guy who starts a key postseason game, but can give you some quality at the back end of a rotation.

If the two were paired up in a deal, that might sweeten the pot a bit in terms of what’s coming back to Chicago – but if I were a betting man, I’d say the Mets probably have a leg up on their division rival in the Kris Bryant sweepstakes at this point.