Since returning to Major League Soccer, Parkhurst has missed one start with the Black & Gold over the last two years. His 20 games of playoff experience help on a fairly young team seeking a championship, but that is the one thing that has eluded Parkhurst.
The center defender went to three consecutive MLS Cup Finals with the Revolution in his first three years in the league, but lost each time.
On Sunday, Parkhurst makes his fourth appearance in the league's championship game, this time with Crew SC.
"I've had my opportunities and I'm glad I did when I was young," he said on Wednesday. "I didn't take it for granted back then, but of course you never know when you'll get another shot, if you'll get another shot."
The most excruciating thing for the Columbus captain is how he lost in the championship games. The Finals have not been kind to Parkhurst, who came so close to winning in each of his three appearances.
"I think a lot of guys know how close I've been," he said. "Seven minutes away in one Cup and having the lead in two Cups.
"I still remember all three games vividly."
In 2005, the East-best New England went to overtime with the LA Galaxy after 90 minutes of scoreless soccer only to see Galaxy midfielder Guillermo Ramírez scored the winner in the 107th minute. The following year, the Revolution again went to overtime at 0-0, but scored first in the extra period before the Houston Dynamo equalized a minute later and won the game 4-3 on penalty kicks.
In his last MLS Cup match, the Revs again took the lead, this time early in the match before Houston scored two second half goals to win back-to-back titles and make New England the Buffalo Bills of the MLS.
Those three losses are fresh in Parkhurst's mind this week and something he's using as motivation as he prepares to face the Portland Timbers on Sunday.
"It's definitely a driving factor personally," he admitted. "To know what it feels like to walk off the field and go into that locker room and hear the celebrations going on next door. The season's over, being dejected. It's not a feeling I want any of these guys to endure, especially this year. So it's definitely a driving factor."
This time around, Parkhurst is with a new team, a different team, and he hopes that will change his MLS Cup fortunes.
"It's definitely different. I think it's tougher now, I really do. It's tougher to make the playoffs, it's tougher to make a run in the playoffs," Parkhurst said.
"Obviously the team that we have is a little younger than those New England teams that I was on. We had a lot of veteran guys and a lot of guys that had played in MLS Cup prior to me even making it. This is different and it's sweet definitely."
While Parkhurst has been unfortunate not to win an MLS Cup, he is blessed to have played in three Finals. At 31-years old, Parkhurst wants to make sure he takes care of business this time as it could be the last opportunity he gets.
"Now that I'm a little bit older, who knows? Maybe this is my last shot," he said. "Hopefully not. Hopefully we make a thing of it and we're here for the next few years, but soccer's weird, you never know. I definitely want to make the most of it. I think all the guys in the locker room understand that. There's no givens. No one knows what the future holds. This could be everyone's only MLS Cup chance so we definitely want to take advantage of it."
As Crew SC captain and one of the few players who have been in this position before, Parkhurst will be relied on this week to help ensure his team prepared. Will he address his losses with his teammates as a cautionary tale?
"I haven't spoken yet about it," he said. "Maybe I will at the right time, but I haven't yet."