Hi Ryan,

Thank you for contacting Mearto with your appraisal inquiry.
John Kennedy's graceful bronze sculptures began to be sold at auction in 2014 and, since then, about a dozen works have been offered, bringing prices between $325 and $1800.
No other Lifetime Achievement Awards have been offered, and that this belonged to Sean Connery, all adds to the value, though that's somewhat difficult to quantify.
If you have documentation (letters, photographs) confirming the provenance to Sean Connery, that will help this bring what could be a new auction record for the artist, if you were to sell it at auction.
Based on the photos and information provided, and subject to examination, this is:

John Kennedy (California, 1931 - 2004)
Lifetime Achievement Award given to actor Sean Connery
1995, awarded in 2001
The stylized jester figure standing on one leg on a domed base signed "J. Kennedy 95", on a circular base.
21 inches high, base 6 inches high
CONDITION: appears to be in good condition
PROVENANCE: gift from actor Sean Connery.
$3,000-5,000*
*represents a fair-market value for auction purposes; retail or asking price may vary.

Please let us know if you have additional items to appraise, and thank you again for using Mearto.