Late in my Knothole (Little League) career my team acquired another pitcher. Let me call him “Lefty”. I was a little apprehensive about his joining the team at first since it might cut into my innings on the mound. We soon became great friends and teammates. We were a one-two punch; he was lefthanded and I was righthanded. Often, we would each pitch 3-4 innings in a game which would put our opponents on their heels. Lefty was more of a power pitcher; my out pitch was a curveball. Lefty though had one big advantage over me. He had a tremendous pick off move, something that many lefthanded pitchers love to exploit.

From a pitcher’s perspective, there are several reasons to execute a pickoff attempt. The obvious one is to actually pick off the baserunner and record an out. That’s not always so easy, especially with alert baserunners. Sometimes, the reputation of having a good pickoff throw holds the baserunner closer to the bag and prevents a steal attempt. In situations late in games when the offense may be attempting a bunt, it’s often good for a pitcher to attempt a pickoff to see if the batter will show his hand by squaring for a bunt. And then there’s the old delay tactic, a signal from the dugout to try a pickoff to buy more time for a reliever to warm up.

The big advantage lefthanded pitchers have is in the mechanics. With a runner on first, a righthanded pitcher must first step with his left, non-pivot foot toward the base. A lefty can make the attempt as part of his regular pitching motion, and simply needs to be careful not to cross his right leg beyond his left one. It can be really deceptive. With a runner on second base, the mechanics are not so different for right and lefthanded pitchers. You can either use a “spin move”, where you spin 180 degrees toward second, or an “inside move” where you try and mimic your normal leg kick to the plate. With runners on first and third base, righties with moderate success used to step off the rubber, fake a throw to third, and then peg a throw to first. MLB made that technique illegal about ten years ago.

Pickoff records are kind of imprecise since they are not an official, MLB statistic. Historically, box scores did not make a distinction between being picked off and caught stealing. A more reknown “Lefty” is hall of famer Steve Carlton, who leads MLB with 145 career pickoffs during his 23-year career. Carlton’s overall stats include a 329-244 win-loss record, an ERA of 3.22, and 4,136 strikeouts. He was a ten-time All-Star and two-time World Series champion. In addition to his career wins and strikeouts at the top of the MLB all-time leaders, Steve was the first pitcher to win four Cy Young awards. One last record to go along with his career pickoffs is that Carlton committed the most career balks of any pitcher with 90. Sometimes that lefty deception went a little too far.

There have been other top lefthanded MLB pitchers quite good with the pickoff move. Andy Pettitte, who spent his 16-year career on the hill mostly with the Yankees, is an example. Pettitte won five World Series as a New Yorker and is MLB’s all-time postseason leader with 19 wins. He had an excellent pickoff move, recording 101 of them in his stellar career. Another includes Mark Buehrle, who starred on the mound for the Chicago White Sox.

Two active MLB lefties are also noteworthy. Clayton Kershaw of the Dodgers, who many consider one of the greatest of all time, has an unbelievable 214-94 record with a 2.51 ERA, and is the on the verge of topping the 3,000 strikeout mark. His pickoff move is widely regarded as one of the best in the game. A somewhat lesser known star, Max Fried, is now pitching for the Yankees after eight years with the Braves. His record is sterling at 82-38, and a lot of the reason for it is his Gold Gloves on the mound (three so far), including his control of baserunners and exceptional pickoff move. Don’t stray too far with Max on the rubber!

Matthew Boyd of the Cubs and his remarkable pickoff move may hold one of the keys to Chicago’s success this season. With the starting staff decimated by the season-ending injury to Justin Steele and seven-week absence of Shota Imanaga, Boyd and Jamison Taillon have been asked to shoulder the load. Boyd’s first half finds him at 6-3 with a 2.84 ERA. In his second to last start, he picked off a baserunner for the third straight game and has done so already six times in 2025! According to Boyd, he developed his move at age 9 when he was at a baseball camp. His instructor at the time apparently joked “if you don’t like someone, you hit him and then pick him off”. The HBP is not in Boyd’s repertoire at the big league level.

Picking off a baserunner has become harder with the new MLB rules. Pitchers are only allowed two pickoff attempts per plate appearance before a balk is called. With unlimited pickoff attempts, pitchers used to have the ability to disrupt a baserunner’s timing by showing different moves. Today, the limit on attempts includes “disengagements”, for example, simply stepping off the rubber. With the advent of the pitch clock, a baserunner can see how much time a pitcher has left to throw to the plate or to the base. Holding a baserunner by not going into a throwing motion is indeed impacted as well.

My friend Lefty and I saw each other at a team gathering a few years ago and reminisced about our pitching days together. Lefty went on to play in college. He was an accomplished hitter too. He told me about an embarrassing moment during his freshman year. You see, he led off an inning by lining a base hit into the gap in right center field. An upperclassman shortstop on the opposing team signaled for him to slow down since it had been ruled a ground rule double. In fact, there had been no such call. As Lefty nonchalantly stepped toward the bag, the shortstop applied the tag. Lefty was picked off. Sometimes, even the best ones are.

Until next Monday,

your Baseball Bench Coach