The Longest Flirtation In Baseball

For those who love the will-they-won’t-they back-and-forth of a classic rom-com, Major League Baseball has a story for you. The Chicago White Sox and lefty hurler Gio Gonzalez are drawn to each other. There’s no denying the connection. They’re the Ross and Rachel of the MLB (or Jim and Pam, or whatever reference is relevant these days). Though they’ve never stayed together long, these would-be soulmates are on the verge of finally making it work. Should baseball return in 2020, their long-standing flirtation should finally consummate with Gonzalez in black-and-white, taking the hill in front of the Southside faithful.

Gonzalez, 34, has long been a productive pitcher in the bigs, but he hasn’t gotten the respect he deserves of late. Though Gonzalez is aging, he certainly pitched well enough to prove himself a viable rotation candidate. And yet, following the 2018 season, Gonzalez languished on the free-agent market. He eventually accepted a minor league deal with the Yankees, but he never made an appearance for their big-league team. He found his way back to Milwaukee where he went 3-2 with a 3.50 ERA/4.04 FIP across 87 1/3 innings (17 starts). Again, solid numbers for Gonzalez, but again there wasn’t much buzz around him as he returned to free agency.

Fear not, for an old friend came to the rescue. The White Sox signed Gonzalez to a $5MM guarantee just before Christmas with plans of slotting him into the rotation. The White Sox are a team on the rise with a young rotation in need of guaranteed, quality innings. Lucas Giolito and Dallas Keuchel are set to front the rotation with less proven assets like Reynaldo Lopez and Dylan Cease likely to follow. Gonzalez should help the young arms take their time and weather the storm, should there be one.

Regardless of fit, we know the White Sox like Gonzalez. This was, after all, the third time they’d acquired him. The White Sox first drafted Gonzalez 38th overall in the 2004 June Draft. But he didn’t last long in their system, as the Sox traded Gonzalez to the Phillies after the 2005 season (with Aaron Rowand and Daniel Haigwood) for Jim Thome.

Just a year later, Gonzalez found himself headed back to Chicago. The White Sox and Phillies connected on a new deal wherein the Phils acquired Freddy Garcia for Gonzalez and Gavin Floyd. Garcia made just 11 starts for the Phillies before leaving as a free agent after 2007. Floyd found his sea legs in Chicago after struggling to make good on his top draft pick status in Philly. He ended up playing seven seasons with the White Sox, going 63-65 with a 4.22 ERA/4.20 FIP in that time, settling in as a decent rotation piece.

Gonzalez’s second stint with the White Sox lasted barely longer than the first. He did, however, begin to flourish. Upon his return, Gonzalez quickly became a top arm in their system, topping out of as their number one ranked prospect by Baseball America in 2008 (#26 overall in the majors).

Still, they traded him – again – this time to the Oakland Athletics (along with Fautino De Los Santos and Ryan Sweeney) in exchange for Nick Swisher. Swisher was a personality match with the White Sox, a spiritual successor to Rowand and other hard-nosed dirt dogs to play on the grass in Chicago – but he only lasted one season (.219/.332/.410 with 24 home runs).

Gonzalez became the gem of that deal for Oakland, making his debut in 2008 as a 22-year-old. It took Gonzalez a couple seasons to find his footing, but by the end of 2011, Gonzalez was an established pro. He put together back-to-back 200-inning seasons for the A’s, amassing 8.3 rWAR/6.5 fWAR across 2010 and 2011 before Oakland shipped him to Washington.

At this point, Gonzalez was entering his age-26 season with some runway to finally settle in after being traded four times already. Gonzalez became a rotation stalwart for the Nationals from 2012 to 2018, a two-time All-Star, and a 124-game winner.

His best season was his first in Washington. The 26-year-old Gonzalez led the league in wins going 21-8 with a 2.89 ERA/2.82 FIP across 199 1/3 innings. As the Nats’ nominal ace, Gonzalez led them to their first-ever postseason appearance. Of course, this was the season the Nationals famously withheld Stephen Strasburg from the playoffs to ensure his long-term health. An undercurrent of that story, however, was Gonzalez, whose dominance that year made such a bold move possible. Gio started games one and five of the NLDS, pitching well but lasting just five innings in both outings – a common thread for Gonzalez. The Nats went 1-1 in those games but ultimately lost the series to the Cardinals.

Gonzalez never put up another season quite like his 2012, but he nonetheless gave the Nats solid work for 6+ seasons. Regardless, there wasn’t a ton of interest when the Nats shopped him during the 2018 season. Gonzalez was eventually traded to the Brewers, for whom he pitched well in five late-season starts. He even got a pair of postseason starts, though he went just two innings in the first outing and left due to injury one inning into his second.

Eight seasons after arriving in Washington and 16 years after Chicago selected him in the first round, Gonzalez may finally have the opportunity to pitch for the White Sox. Of course, a lot stands in the way of Gonzalez making his debut in Chicago, but that’s nothing new. Now in his third stint in the organization, the White Sox hope Gonzalez will help lead this young team.

Of course, if they don’t make the leap many expect, Chicago could embark on one last selloff of veterans before making a run at contention again in 2021. If that happens, Gonzalez could find his name in the trade papers once again. But for now, as before, Gio Gonzalez is a member of the Chicago White Sox.