Tim Dierkes at MLBTR has the official Super Two cut-off for this year, and it’s two years and 116 days – meaning players with at least that much service time, but shy of three years, will qualify for arbitration this offseason. They’ll get four turns through arbitration, rather than just three.
For the Cubs, this news confirms that newly-acquired outfielder Harold Ramirez will be a Super Two, though that was expected even as of the time of the trade (two years and 124 days). He’s projected by MLBTR to get a bump to $1.6 million in arbitration, which is a healthy amount for a guy on whom the Cubs are taking a flyer as a 4th outfielder. But, again, they knew this was likely when they acquired him from the Guardians, so either they’re cool with the price tag, or they were planning to try to sign him before the tender deadline in three days. If the Cubs retain Ramirez, they’ll have him for the next four seasons via arbitration. Assuming the arbitration system doesn’t fundamentally change in the CBA, of course.
Falling just short of Super Two status, though, is reliever Rowan Wick (two years and 114 days). Given his missed time, it’s possible he wouldn’t have gotten THAT much more in arbitration than he’s going to get as a pre-arb player (the Cubs give raises along the way), but it still has to be a blow to learn he was just two days short of getting a bump (and subsequent bumps in his next three arb turns). Wick will still be under team control for four more seasons, with the latter three being via arbitration.
Alec Mills would’ve been the next closest, at two years and 97 days.