This season has been an tumultuous one for the Tampa Bay Rays, who are playing in the New York Yankees’ spring training facility this season while Tropicana Field undergoes repairs following damage sustained during Hurricane Milton. But the Rays have had a successful season, sitting just five and a half games behind the Toronto Blue Jays for first place in a hotly-contested AL East. They currently trail the Seattle Mariners by 1.5 games for the final Wild Card spot.
Tampa Bay hasn’t had a player lead all of the major leagues in any hitting stat category since Carl Crawford hit 19 triples in 2004. Thankfully for Rays fans, that streak is likely to end this season; at the All-Star break, José Caballero leads all of the majors with 31 steals, and his teammate Chandler Simpson has 26 in just 53 games. Simpson is a +140 favorite to finish with the most steals at DraftKings Sportsbook, with Caballero right behind him at +340. The non-Ray with the shortest odds is the Cincinnati Reds’ Elly De La Cruz, who led all of baseball with 67 steals last season.
Best Bet: Chandler Simpson Most Regular Season Stolen Bases (+140)
While Caballero currently has more steals than Simpson, getting the rookie at plus odds is a steal (pun intended). Not only does the 24-year-old have the eighth-fastest average sprint speed in all of baseball — a category in which Caballero ranks just 168th — he also has a .340 OBP, which would rank 64th in the league if he’d had enough plate appearances to qualify. He should have more base-stealing opportunities than Caballero, whose OBP is just .313, Oneil Cruz (.319), or Pete Crow-Armstrong (.302). Plus, since he has no power — his bat speed would be the fifth-slowest in the majors if he’d had enough plate appearances to qualify and he has just seven extra-base hits all season — every time he gets on base, it’s first base.
Simpson has only played 53 games because Tampa Bay sent him back down to Triple-A, where he slashed .333/.370/.396 with 19 stolen bases in 33 games. The extra seasoning worked: since returning to the majors, he has slashed .355/.388/.419, with seven stolen bases in 18 games, and he hasn’t had a hitless game yet in July. Unless the Rays are seriously concerned about his lackluster fielding, he should be an everyday starter, and his elite contact tools should make him a valuable asset.
Caballero, meanwhile, is in the middle of a slump. Over his last 17 games, he’s only gotten on base 15 times, slashing .167/.274/.185 across that span. He’s only played seven games in July, while Simpson has played in all but one game this month, so while it’s unlikely that Tampa Bay sends the 28-year-old down or releases him, especially thanks to his above-average fielding, his spot in the lineup is clearly more tenuous than Simpson’s. Even at +340 odds, momentum is clearly not in his favor.
Of the non-Rays, De La Cruz has the best shot, though he’s recorded fewer steals than Simpson has while playing nearly twice as many games. The 23-year-old is getting on base at a higher rate than Simpson is this season, but he’s been less aggressive on the base paths this season than he was in 2024. Ramírez’s 29 steals already represent the third-highest total of his career, and he gets on base more frequently than Simpson does, but more of his times on base are extra-base hits. Cruz and Crow-Armstrong simply don’t get on base enough. Simpson will run away with this one as long as he continues to get regular playing time.
