The Chicago Cubs have reached the Last Dance stage with their core roster, and a reckoning awaits.
The Boston Red Sox are entering the Middle School Dance phase of their rebuild, shyly inching towards the center of the gym in the hopes of finding a partner.
Could the two clubs be a match before the Aug. 31 trade deadline? They sure could, and here's the player who should most pique Chicago's interest: Brandon Workman.
Four years after ending a century-long World Series drought, the Cubs are rolling. They're 10-3 and have the most wins in the National League (though not technically the best record, since the Miami Marlins are somehow 6-1).
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They feature the best starting pitching in the National League (9-3, 2.83), and the Ian Happ-led offense ranks fourth in runs and second in homers.
They are, however, a contender with one glaring weakness: their bullpen. Cubs relievers own a 7.30 ERA, and their problems are particularly acute at the back of the 'pen, where closer Craig Kimbrel is pitching himself right out of a job. In four appearances covering 2.2 innings, Kimbrel has allowed seven runs on six hits and five walks, as well as two home runs. Perhaps most shockingly, he has struck out only two of 20 batters faced. Coming on the heels of an 0-4, 6.53 debut last season, Kimbrel claims he is working through his issues. However, he's starting to look like a lost cause.
Boston Red Sox
The Cubs badly need a bullpen upgrade, and the Red Sox know they're probably going to lose Workman in free agency this winter. A trade to Chicago makes sense on multiple levels.
First, and most obviously, the Cubs need a reliable arm at the back end. Workman saved 16 games while going 10-1 last year, and he's got two saves so far this year. His mix of a dominant curveball and 95 mph fastball gives him the stuff to pitch in the late innings, and his makeup and demeanor lend him an air of unflappability that can play in the most intense glare of October, as he proved during the 2013 World Series.
So from a purely baseball perspective, Workman represents a clear upgrade. But there's a personal connection, too, because Cubs president Theo Epstein drafted Workman out of Texas in the second round of the 2010 MLB Draft before signing him to an $800,000 bonus. Epstein oversaw Workman's first professional season in 2011, when he went 6-7 as a starter at Class-A Greenville, and Epstein took pride from afar in the contributions that his former farmhands made to the 2013 crown.
Furthermore, Cubs manager David Ross caught Workman that year, including his scoreless eighth inning in Game 6 of the World Series clincher vs. the St. Louis Cardinals. Ross has seen Workman's mental toughness up close, such as during the 2014 season, when Workman went 1-10 before undergoing Tommy John surgery that ended up sidelining him for two full seasons.
In addition to those personal connections, there's also the big picture. Chicago's championship core of first baseman Anthony Rizzo, third baseman Kris Bryant, shortstop Javier Baez, left-hander Jon Lester, and outfielder Kyle Schwarber will hit free agency either this winter or next. Since winning it all, the group has lost an NLCS and a Wild Card game, and last year it missed the playoffs entirely.
The Cubs' window is closing, but the early returns on 2020 suggest they could be poised to make one last run. Their farm system isn't what it used to be, and the Red Sox need to be realistic about what kind of return they can expect for a relief rental in a season that has already been shortened by a pandemic, but perhaps there's a deal to be made for a second-tier prospect like right-hander Keegan Thompson or left-hander Jack Patterson.