#2 Jamal Crawford
Last season, Crawford was still a free agent at around this time and I wrote about how he will be signed by a team soon. Crawford, who is 39 now, is entering his 19th season in the league. He has played for the Chicago Bulls, New York Knicks, Golden State Warriors, Atlanta Hawks, Portland Trail Blazers, Los Angeles Clippers, Minnesota Timberwolves, and last season he signed with the Phoenix Suns.
Clearly, he has moved around the league plenty of times, but the 2019-20 season could either be his last season or he will call it a day and we will not see him win a championship after all those years.
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Yes, Crawford deserves an NBA championship title after spending years on different teams. But it seems like he simply plays for the love of the game and not to chase a ring, since he could have signed with a contender but chose to sign with the Suns.
He would definitely benefit a young team, being a presence and/or mentor, as well as coming off the bench and scoring once in a while. The 3-time NBA Sixth Man of the Year should hopefully be signed soon, likely after the season starts.