Prior to the beginning of the 2022 season, Judge had also set a deadline for negotiating a contract extension. If it didn't happen before the start of the regular season, then he was going to become a free agent.
Sure enough, the deadline came and went without a deal, and Judge cut off talks. He then went on to have one of the best years in modern memories.
When JJudge officially entered free agency, there was a feeding frenzy. Although rumours abounded that he might leave New York and sign with the Giants, Judge ultimately re-signed a nine year, $360MM deal with the Yankees.
The Blue Jays find themselves in a similar situation with Vladimir Guerrero Jr. After no deal on an extension was reached before Tuesday's deadline, Guerrero heads in 2025 without a guaranteed contract beyond October.
While many are concerned that this will be his last year in a Blue Jays uniform, others aren't so sure, and point to Judge as evidence.
And while contracts have soared substantially in the years Judge signed, many are optimistic that a reunion between Vladdy and the Blue Jays is still possible.
Many analysts have opined that Vladdy simply wants to feel the feeling of being a free agent and being wanted by other teams.
From a Blue Jays perspective, a Guerrero free agency would be a good test of the market and good gauge of other teams valuations versus their own.
Either way, Vladdy is still a Blue Jay for a least a little while longer.