Back in 2010, the White Sox catcher suited up for what could have been his last game with the organization with free agency looming. That season finale happened to be at home, unlike Sunday's contest against the Rays, which will be followed by three more this week in Cleveland.
With Pierzynski's two-year extension coming to an end after the season, the veteran backstop once again faced the prospect of playing his last game for the White Sox at U.S. Cellular Field during Sunday's 6-2 loss to the Rays.
"There's definitely a chance it could be," Pierzynski said. "You know, it's kind of bittersweet. On the one hand, obviously we would like to be in a better position than where we are at. But hopefully, we'll find a way to win these last four games and come back and have a couple more home games."
The White Sox exited Sunday's series finale with the Rays trailing the Tigers by three games with three to play, so their postseason prospects look all but completely wiped away. The fact that his team stayed in contention until the final days of the regular season hasn't given Pierzynski much time to think about the future.
Pierzynski has stated on numerous occasions that he would like to stay with Chicago. In 2010, Pierzynski was close to signing a new deal with the Dodgers before the White Sox came in at the 11th hour with a two-year, $8 million extension he couldn't refuse.
Tyler Flowers waits in the wings as possibly the next in line behind the plate. So while Pierzynski has loved his time in Chicago as much as the fans have enjoyed having him, he's ready to move on if the situation dictates.
"Like I said earlier in the season, I packed my house up once, I packed it up for a second time. It's becoming old hat now," said Pierzynski, whose wife and two children flew in for what could be his final home game with the White Sox. "I would love to come back and finish my career here, but at the same time, I know how baseball works.
"Maybe we can work something out. If not, I'll always look back fondly on my time here and appreciate it. I love the city of Chicago. I love the fans here. I love the people here. I love the organization, and you'll never hear me say anything bad about them.
"Everything comes to an end at a certain time. I hope it's not the end, but if it is, I'll look back fondly and with great memories and hold my head high, because I know I gave everything I could to the White Sox organization. I hope people remember that."
If this is Pierzynski's last of his eight years with the White Sox, he went out on a high note. Not only did he work with 10 rookie pitchers this season, but he also set a career high in home runs (27) along with 76 RBIs.
"I'm very grateful for that. Very thankful for that," said Pierzynski of his White Sox tenure. "[General manager] Kenny [Williams] kind of took a flyer on me in the '05 season and we went on to win the World Series, and I've been here ever since. It's been great. It's been a great run. Hopefully, it will continue."