3 of the best Cubs trade deadline deals in franchise history and 2 of the worst

July is fast approaching and with it inevitably comes the flying of trade rumors. The Chicago Cubs still aren't solidified in where they'll land this year - at three games below .500 and behind two NL Central competitors, they're not in the best position for a run. At only three games behind the Brewers and Reds who are tied at the top, however, it would be easy for Jed Hoyer and company to make an excuse to do some light buying this year.

Trade deadlines have been a touchy subject for Cubs fans over the past two years. 2021 and 2022 saw major sell-offs that sent franchise faces and valuable pieces to greener pastures as the team built for the future. Whether as buyers or sellers, however, the Cubs have a long history of shaking it up with midseason deals. Some of these have vastly improved the team's fortunes and brought franchise favorites to town, while others are still sources of derision today.

As we head toward an uncertain 2023 trade season, let's take a look back at three of the best, and two of the worst, deal the Cubs have made at and around the trade deadline.

#1 Best: Cubs acquire Jake Arrieta and Pedro Strop from Baltimore for Scott Feldman

It's hard to find a better trade season deal than landing both a rotation and relief ace in a total steal. That's what the Cubs accomplished in 2013 when they picked up both Jake Arrieta and Pedro Strop for the low low price of Scott Feldman in an early July swap with Baltimore.

From the Orioles' side of things, it's a disaster deal in hindsight. After posting a 3.46 ERA in Chicago, his ERA rose to a mediocre 4.27 in Baltimore. He would also only stick around for the second half of that season before walking and signing with the Astros. The Cubs, meanwhile, would get years of valuable service out of Arrieta and Strop. Arrieta would become the team's ace, winning a Cy Young in 2015 and posting a 2.67 ERA in his four full seasons with the team. Strop, meanwhile, would become a bullpen stalwart with a 2.90 ERA in his six full seasons after 2013.

Of course, both pitchers would be key pieces to the 2016 World Series roster, helping the Cubs form a deadly pitching staff that would be the envy of the league. Both were solid in their appearances against Cleveland, playing their part in breaking the 108-year championship drought.

#1 Worst: Cubs Acquire Ernie Broglio from St. Louis for Lou Brock

There's a reason why we keep beating this dead horse. Lou Brock for Ernie Broglio is so infamously bad it has its own Wikipedia page dedicated to it. It still haunts the Cubs in many ways to this day. While there were other players involved in this deal, it was only Broglio and Brock that truly mattered in the grand scheme of things.

Before the 1964 deadline, the Cubs would make the ultimate blunder by trading for Broglio and sending Brock along with two other players in the package deal. It seemed like a steal at the time since Broglio had come off multiple successful seasons in St. Louis. As it was later revealed, however, Broglio had dealt with a shoulder injury in 1963 that eventually required more work in November of 1964. He'd post a pedestrian 4.04 ERA in the 100 1/3 innings after the deal, but after that, the wheels would fully come off as he'd only pitch two more seasons and post a 6.61 ERA across only 113 innings.

Brock, meanwhile, could have his own chapter in the Cardinals' history book. In St. Louis, he'd eclipse 3,000 hits, become the all-time stolen base leader (until Rickey Henderson came along), make the NL All-Star team six times, make the Hall of Fame, and help the Redbirds to not one, but two World Series wins including 1964. For two and a half miserable years of Broglio, they received 15 1/2 incredible years of Brock. It was clear the Cubs weren't utilizing Brock's skills correctly, but the results of this trade are mind-bogglingly bad nonetheless.

#2 Worst: Cubs acquire Jose Quintana from White Sox for Eloy Jimenez and Dylan Cease

The Cubs gave a gift to their crosstown rivals in 2017 with a trade that gets worse by the day. In need of an excellent starting pitcher to bolster their rotation, they linked up with the White Sox to bring Jose Quintana over to Wrigley Field. He seemed like a potential ace at the time, coming off of three straight years of sub-3.50 ERA baseball while remaining incredibly durable, eclipsing the 200-inning mark in every year beyond his rookie campaign.

A player of that caliber, understandably, required a high price. The Cubs sent two of their top prospects, Eloy Jimenez and Dylan Cease to the South Side to reel in Quintana. Both prospects seemed redundant for the Cubs. They lacked a true spot for Jimenez with no DH and, since they were acquiring Quintana and already had Jon Lester and Kyle Hendricks around for a while, they could deal with losing Cease.

Unfortunately, Quintana wasn't the pitcher they hoped for at all. After pitching to a respectable 3.79 ERA the rest of the way with the Cubs in 2017, he'd struggle against the Dodgers in the postseason and never had an ERA below four again. Meanwhile, Jimenez would become an All-Star caliber bat with the White Sox, even if injuries would become an issue, and Cease would blossom into a Cy Young caliber arm, finishing second for the award in 2022. Oh, and he, too, is very durable. In an era where the Cubs needed an ace, they had to watch their former prospect become one in real time.

What makes this one all the more painful is who they COULD have had. Fans are well aware that Justin Verlander was on the market and had a desire to play on the North side. It's hard to blame the Cubs at the time for choosing the young, controllable pitcher, but it stung to see Verlander go on to post a 1.06 ERA in an Astros uniform and propel the team to their first, if tainted, World Series. He'd continue to age like a fine win in Houston too, winning two more Cy Youngs in 2019 and 2022.

Even if it meant losing Cease and Jimenez, having Verlander instead of Quintana for those few years after would've been a major consolation. Quintana was perfectly ok, but very far from what the team paid for.

#3 Best: Cubs Acquire Kenny Lofton and Aramis Ramirez from Pittsburgh

Back in 2003, the Cubs would swing a deal that would bolster their chances in the playoffs significantly and add a pair of fan favorites. Although not remembered quite like the highway robbery that was Brock for Broglio or Strop and Arrieta for Feldman, nabbing Aramis Ramirez and Kenny Lofton from the Pirates was arguably the most lopsided trade in the Cubs' favor.

For the cost of only Mike Bruback, Jose Hernandez, and Bobby Hill - all of whom would be out of Pittsburgh by 2005 - the Cubs got their answer at third base for the next eight years along with a stellar veteran who was crucial to their postseason success. Ramirez began well enough with a 106 wRC+ in 2003, but he'd blossom afterward with a .297/.359/.533 slash line and a 128 wRC+ from 2004 through 2011 with a pair of All-Star nods and a Silver Slugger.

Lofton, who's also a brutal Hall of Fame snub, was excellent in his half-season on the North side with a .327/.381/.471 line, good for a 121 wRC+ at age 36. He wouldn't lose much steam in the postseason either with a .308/.368/.346 slash line across the team's run. Even if he didn't stay beyond 2003, he still made an impact as one of the Cubs' best rentals in their history.

Though the Cubs didn't get their World Series in 2003, the pickup of Ramirez and Lofton hit the perfect blend of short term value while setting up for the future. This team has had several deals blow up in their faces, but when they've gotten them right as they did here, they've prospered well beyond that year's trade deadline.