Jaylen Brown is becoming the richest player in NBA history with his new $304 million extension. But Brown is really just the first of a parade of players who will be making history with their contracts. John Karalis of Boston Sports Journal and Tom Westerholm discuss Brown's new deal, the pressure he'll face to live up to it both from himself and from the outside, and how this impacts his future in Boston. Support Us By Supporting Our Sponsors! PrizePicks First time users can receive a 100% instant deposit match up to $100 with promo code LOCKEDON. That’s PrizePicks.com – promo code; LOCKEDON FanDuel Make Every Moment More. Don’t miss the chance to get your No Sweat First Bet up to TWO HUNDRED DOLLARS in Bonus Bets when you go FanDuel.com/LOCKEDON. FANDUEL DISCLAIMER: 21+ in select states. First online real money wager only. Bonus issued as nonwithdrawable free bets that expires in 14 days. Restrictions apply. See terms at sportsbook.fanduel.com. Gambling Problem? Call 1-800-GAMBLER or visit FanDuel.com/RG (CO, IA, MD, MI, NJ, PA, IL, VA, WV), 1-800-NEXT-STEP or text NEXTSTEP to 53342 (AZ), 1-888-789-7777 or visit ccpg.org/chat (CT), 1-800-9-WITH-IT (IN), 1-800-522-4700 (WY, KS) or visit ksgamblinghelp.com (KS), 1-877-770-STOP (LA), 1-877-8-HOPENY or text HOPENY (467369) (NY), TN REDLINE 1-800-889-9789 (TN) Learn more about your ad choices. Visit podcastchoices.com/adchoices