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Yankees Trade Partner History: Chicago Cubs

Two of baseball’s oldest franchises have made a number of interesting deals.

World Series - Chicago Cubs v Cleveland Indians - Game Seven Photo by Ezra Shaw/Getty Images

A solid formula for a trade partner is a franchise your age or older, and one in the other league. This ensures plenty of seasons for deals to be made, and lower risk of a deal biting you in the butt given the relative rarity of interleague play. In the last 110 years, the Yankees and Cubs have been involved in some 40 transactions, giving us plenty of possible swaps to look through.

In the last decade or so, the two clubs have been especially active, mirroring each others’ competitive window in a way that allowed each to take advantage of the other’s cycle. Of the nine trades going back to the 2013 season, one of them will almost certainly be included in every retrospective of Brian Cashman’s tenure.

Best Trade

July 25, 2016: The Yankees trade Aroldis Chapman to the Cubs for Rashad Crawford, Billy McKinney, Gleyber Torres, and Adam Warren.

It’s hard to say there’s a real loser in this trade. The one thing Theo Epstein needed to make those 2016 Cubs fully loaded to bear was a shutdown closer, and Chapman boasted a 216 ERA+ and 20 saves for a pretty mediocre Yankee team come deadline day. A good chunk of Yankee fans felt a whole lot of unease given the discount Chapman was acquired at due to his impending domestic violence suggestion, so he was an easy piece to be happy about leaving town.

Epstein got his closer, Chapman had a 418 (!) ERA+ down the stretch to get the Cubs into the postseason, and although he did blow three saves in the playoff run — looking absolutely gassed by the now-legendary Game 7 — he got the ring. More importantly, the Cubs got their rings. We’ll get into what the Cubs gave up in a moment, but perhaps no other trade in history so obviously supports the “flags fly forever” mantra.

On the pure numbers side, the Cubs got 1.3 fWAR out of Chapman, which Torres bested in his first MLB season, 2018. He’s contributed 13.8 wins in total with the Yankees ahead of his final season under team control, and been a 126 wRC+ hitter in 129 postseason PAs, being a reliable contributor in Octobers where we’ve seen the lineup go cold all too often.

He may not be the MVP candidate we thought he might be in the upper minors, but a pair of All-Star appearances and consistent, quality offensive contributions are worth more than many fans think. As a headline, that’s a trade you take every single day. Adding oft-Yankee Adam Warren, who put up a 2.67 ERA in 117.2 innings before being dealt to the Mariners in 2018, was a cherry on the top of the sundae.

Most Overlooked Trade

July 21, 2000: The Yankee trade Ben Ford and Oswaldo Mairena to the Cubs for Glenallen Hill.

In need of some extra punch in the midst of a (for them) mediocre 2000 season, the dynasty Yankees landed a veteran bat who either benefitted from the change of scenery or was due for a dead cat bounce regardless. A .797 OPS in the Senior Circuit became a 1.112 mark in pinstripes, just the depth the team needed in pursuit of their third consecutive World Series crown.

More to the point about this deal is just how little Brian Cashman gave up for that veteran presence. Hill hit more home runs down the stretch — 16 — than both relievers threw combined innings in the 2000 season. Mairena and Ford wouldn’t get regular work in the bigs until 2002 and 2004 respectively.

Worst Trade

July 13, 1987: The Yankees trade Rich Scheid, Bob Tewksbury and Dean Wilkins to the Cubs for Steve Trout.

“I just won you the pennant. I got you Steve Trout.” - George M. Steinbrenner III, to then-manager Lou Piniella

If you’re looking for bad trades, it’s usually a good idea to look in the Peak George era. I wasn’t around in 1987 so it’s hard to see the appeal of Steve Trout, besides him being 6-3 with a 3.00 ERA to open the season. While those numbers were fine enough on their own, he was coming off a dreadful 1986 season and was clearly in the twilight of his career.

Still, George is gonna George, and the big pay here was Mr. Tewksbury. Tewks was in a bit of a sophomore slump following a solid rookie season, but a trade for a youngster to get back a roughly equivalent veteran was the order of the day. In spite of the Boss’ above optimism, Trout did not deliver a pennant, with a 6.60 ERA and unsightly 37 walks in 46.1 innings between the rotation and the ‘pen.

The silver lining is this deal isn’t quite on the Crime Dog level because neither Schneid nor Wilkins turned out to be much of anything. Bob Tewksbury, meanwhile, would have a solid career all the way to 1998, making an All-Star Game and four straight 110 ERA+ seasons as a member of the Cardinals.

Weirdest Trade

July 25, 2016: The Yankees trade Aroldis Chapman to the Cubs for Rashad Crawford, Billy McKinney, Gleyber Torres, and Adam Warren.

Yep, we’re back to this one. In terms of true trade value this is obviously the best deal, but the departure and return of Adam Warren makes this one wonky. The Yankees had sent Warren to the Cubs in December 2015 as part of the Starlin Castro deal, but New York clearly had some seller’s remorse and the North Siders soured on him in a hurry anyway. Warren threw just 35 innings for the Cubs in 2016 before finding himself right back in the Bronx.

Other Trades of Note

August 1, 2022: The Yankees trade Hayden Wesneski to the Cubs for Scott Effross.

We’re still waiting to see where this falls in the scheme of things. Effross has an intriguing profile and is under team control through the end of the 2027 season. He is also rehabbing from Tommy John surgery, and how he returns will say a lot about how we view this deal. Wesneski has been unimpressive so far for the Cubs, with 0.4 fWAR across 122.1 innings.

December 8, 2015: The Cubs trade Starlin Castro to the Yankees for a player to be named later and Adam Warren. The Yankees sent Brendan Ryan (December 17, 2015) to the Cubs to complete the trade.

Starlin and Didi Gregorius made for a deeply entertaining double-play combo, even if the total production from the two left a little something to be desired. Castro was an All-Star in 2017, but is perhaps most important for being part of the Giancarlo Stanton deal in December 2018.

July 26, 2013: The Cubs trade Alfonso Soriano and cash to the Yankees for Corey Black.

Who says you can’t come home again?

The second time Soriano was a Yankee was a little more of a salary dump for the then-tanking Cubbies, but he was still a solid enough contributor at the MLB level. He posted a 118 OPS+ in 2012, and a return to Yankee Stadium seemed to inject a little bit of restorative power in his stick. Sori’s OPS jumped 96 points after being dealt back to New York, and although his next, final season would be a bit of a letdown, 2013 was a lovely continuum for the Top 100 Yankee.

Previously in the Trade Partner History series

Toronto Blue Jays
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