Martin, who was killed in a car accident on Christmas Day 1989, was a longtime Yankees manager and had a 1,253-1,013 career record. Showalter said he was made aware that he was closing in on Martin by his daughter, Allie.
"She knows what Billy meant to me, so from that standpoint I actually find it a little sad," Showalter said of the prospect of tying Martin for 36th on baseball's all-time win list. "It's like one of those things -- I'd like to give him a few so he can go back up there where he should be."
Showalter often quotes Martin, who took him under his wing when Showalter was a coach in the Yankees' Minor League system. He said he's been texting some with Martin's son, Billy Jr.
"He had time for me. And I still don't know why," Showalter said of Martin. "He made time for me. When you were with him those mornings, about 11 o'clock on the back fields in Fort Lauderdale, [Fla.] He would always bring all the Minor League managers in. We'd walk behind him like little chickadees and he'd stop at every drill and talk about this and talk about that, and, 'This is how you need to do this, and this is why.'
"People looked at Billy as some roughneck cartoon character who argued with umpires, but he was brilliant. He had such a feel for the game."
The most important lesson Showalter said he took with him from Martin was to trust your gut and never let numbers and advanced metrics solely dictate your opinion on a player. He was delighted to share the story of Martin, working as a scout in his last year, asking for Showalter's Double-A reports from Albany, a compliment that resonated with Showalter.
"That was pretty cool when I hung up," Showalter said. "If you ask me about Billy, I can talk forever. But he wasn't perfect.
"There's a lot of things you remember in your life, I remember when I got the news that he had been in the car accident. He was one of those guys you felt like he could take yours and beat his and take his and beat yours."
Brittany Ghiroli is a reporter for MLB.com. Read her blog, Britt's Bird Watch, and follow her on Facebook and Twitter @britt_ghiroli. This story was not subject to the approval of Major League Baseball or its clubs.