By Tim Kelly, Sports Talk Philly editor 
The Philadelphia Phillies' connections to the Baltimore Orioles are something you are likely to hear about quite frequently over the course of the next few years.
Three of the Phillies' top decision-makers have connections to the Orioles. President of baseball operations Andy MacPhail served in the same role for the Orioles from June 2007 until the end of the 2011 season. During MacPhail's tenure with the team, current Phillies general manager Matt Klentak was named the team's director of baseball operations, a role he held from 2008-2011. Assistant general manager Ned Rice joined the Phillies front-office after the 2015 season, leaving his role as the Orioles' director of administration.
These connections have caused speculation that the Phillies could potentially be one of the suitors for Orioles third baseman/shortstop Manny Machado if he becomes a free-agent after the 2018 season. Ditto for All-Star closer Zach Britton. But perhaps the most juicy Orioles-related speculation is yet to come.
Ken Rosenthal of FOX Sports noted over the weekend that a power-struggle appears to be brewing between Orioles manager Buck Showalter and general manager Dan Duquette:
I reported on tension between Showalter and Duquette at the end of the 2015 season, and sources tell me that their relationship continues to be unsteady. So, would Showalter want to remain manager if Duquette stays as GM? Or would Showalter, who recently turned 61, prefer to be the GM himself?
There's many layers to this situation, but if Showalter were ever to become available, the connections to the Orioles that the Phillies front-office has would certainly set them up to be a player for his services, right? Well, not exactly. Despite the fact that current manager Pete Mackanin is only contractually guaranteed to be the manager for 2018 — and may even need the team to pick their play up for that to be certain — a future fit for Showalter isn't as good as you might think.
Let's start with the obvious: if there is a need to pick between Showalter and Duquette, there's no reason to think that Orioles owner Peter Angelos wouldn't side with Showalter. Duquette, who became the team's general manager after MacPhail left the front-office, came relatively close to becoming the Blue Jays' president/CEO during the 2014-15 offseason. The Orioles didn't balk at the idea of Duquette leaving to join a division rival, but instead didn't allow him to leave because they were unable to work out a trade with the Blue Jays that appeased them.
Prior to hiring Duquette, Angelos reportedly offered Showalter the chance to replace MacPhail, with Rosenthal also suggesting at that time that Angelos did bring up the idea of Showalter remaining the manager and taking over the front-office in a 2015 Chip Kelly-type role.
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The history of Showalter turning down a chance to be an executive may suggest that he's just not interested in such a role. Certainly, it's hard to imagine him being interested in filling both roles at age 61, if that idea didn't intrigue him when he was in his mid-50s. But the most likely scenario if there's a shake-up is that the Orioles would part with Duquette and allow Showalter to be involved in picking the team's next general manager.
However, the clock is ticking for Showalter. 61 is still relatively young, but it's fair to wonder how many more years he will be able to and/or want to deal with the rigors that managers go through. If the Orioles lose Machado, Britton and Adam Jones after 2018, perhaps Showalter would be interested in leaving with them. While there probably won't be an organization with as much young talent as the Chicago Cubs waiting to catch Showalter on the rebound like the Cubs did with Joe Maddon, there will be plenty of interest in him.
In theory, the Phillies could be coming of age around that time, especially if they are able to add a player like Machado in free-agency. However, with the stunted developments of Vince Velasquez, Maikel Franco and J.P. Crawford, among others, it's fair to wonder if the Phillies would be the most attractive place for Showalter to chase a championship at.
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There's also the fact that MacPhail and Showalter didn't coexist over a long period in Baltimore. MacPhail publicly was the person that decided to hire Showalter during the 2010 season, though there were reports at the time that suggested that he would have preferred to hire a different candidate. MLB.com's Brittany Ghiroli noted when MacPhail decided to leave after the 2011 season that speculation that the two couldn't coexist was overblown, but MacPhail did choose to leave after his first full season of working with Showalter. He did so even as Angelos attempted to retain him.
It may not be as simple as the narrative of MacPhail deciding he couldn't work with Showalter. In his late-50s, he may have been burned out, especially since the Orioles hadn't yet returned to contention. He did cite wanting to spend more time with his family at the time, which makes sense since his father Lee passed away just over a year after he left the Orioles. Angelos also doesn't have a reputation around the league as being an owner who is easy to work with. Still, the idea of MacPhail and Showalter having mutual interest in reuniting in Philadelphia seems unlikely given their brief history together.
There would be something fitting in Showalter joining the Phillies for what they hope is their next great run. After all, he presided over the Orioles team that delivered one of the most painful losses that the Phillies have had during their rebuild, a 19-3 loss in June of 2015. But when you dig a little deeper, a fit that appears natural to some on the surface, isn't so ideal at the core.
