The last time Clayton Kershaw was approaching free agency, in 2018, I wrote a number of times (summed up here) about the likelihood that he would remain with the Dodgers. Because of his unique history in Los Angeles, there was no other team that could sign him for which he could offer more value.
Kershaw will be a free agent again in two months, but the question hasn’t come up as much, because of the 33-year-old’s more advanced age and injury issues. Nevertheless, it’s worth noting that as long as he wants to pitch, it continues to make the most sense for him to stay with the Dodgers. While he shouldn’t command the same salary of his last contract, no contender is better equipped to pay him the dollars he will end up earning.