Complex sentence: As his streak continued deeper into the 21st season, Jennings was inching closer and closer to Olmstead's record, which he ultimately topped with his 65th consecutive win, finishing the day with $45,099 and a new cumulative total of $2,197,000.
Split into simpler sentences: As his streak continued deeper into the 21st season, Jennings was inching closer and closer to Olmstead's record. Jennings topped Olmstead's "Millionaire" winnings with his 65th consecutive win, finishing the day with $45,099 and a new cumulative total of $2,197,000.