It might happen this week, or the next week, or the next. Soon enough, Kathleen O’Connell will be the all-time winningest female trainer in North American racing history. O’Connell began this week with 2,382 career wins, just three behind Kim Hammond, who is winding down her career. Both women have been training for more than 40 years. “It’s an honor, but it’s not something I set out to do,” O’Connell said recently from her Tampa Bay Downs base. “It basically puts a number on a lifetime. It’s what I do every day.” O’Connell, 64, splits her time between Tampa and Gulfstream Park in the winter and spring before moving to Monmouth Park (while also maintaining a string at Gulfstream) for the summer and fall. It’s been the type of hectic routine she has followed since she ran her first winner at the old Detroit Race Course in 1981. She left her native Michigan for Florida for good a few years after that, having learned the ropes under several mentors, with much of her expertise being self-taught. Among the stakes winners trained by O’Connell were Blazing Sword, Ivanavinalot, Watch Me Go, Stormy Embrace, and Well Defined. Ivanavinalot went on to become the dam of Songbird. O’Connell still climbs aboard her pony every day for morning training. “I don’t know when I’ll retire,” she said. “There are some things happening right now that are making the game more difficult than it should be. I guess I’ll know when it’s time.” :: Bet the races on DRF Bets! Sign up with code WINNING to get a $250 Deposit Match, $10 Free Bet, and FREE DRF Formulator.  Hammond, 65, has won 2,385 races since she began training in 1980, mostly at smaller tracks in Illinois, Indiana, and surrounding states. She said last weekend from her Indiana farm that although she still has about 30 horses in her care, some at Turfway Park in Kentucky, she intends to retire by the end of 2023. “It’s time,” she said. As for the results of her four-plus decades in racing, “I’m tickled pink. It was bound to happen that someone would pass me, and I’m fine with it. Tell Kathleen to keep going strong.” Linda Rice follows Hammond and O’Connell on the all-time list with 2,264 winners through Sunday. Rice, based in New York, is by far the leader in career stable earnings with more than $95 million. The next two on the wins list, Christine Janks and Stephanie Beattie, both have retired. Janks ran her last starter in 2015 and Beattie in 2017. Steve Asmussen is the all-time wins leader in North America, having reached the 10,000 mark on Feb. 20. Gai Waterhouse of Australia is widely acknowledged as the leading female trainer in the world with more than 7,000 wins. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.