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Tito Could Have Predicted End with Red Sox By Watching Entourage

A Sports Blog by 98.5 The Sports Hub's Adam Kaufman
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Actors Kevin Dillon, Jeremy Piven, Adrian Grenier, Jerry Ferrara and Kevin Connolly arrive at the premiere of HBO's 'Entourage' season 7 at Paramount Studios on June 16, 2010 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)

Actors Kevin Dillon, Jeremy Piven, Adrian Grenier, Jerry Ferrara and Kevin Connolly arrive at the premiere of HBO’s ‘Entourage’ season 7 at Paramount Studios on June 16, 2010 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)

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BOSTON (CBS) -September marked the frustrating end of two substantial parts of my life: Terry Francona’s managerial run in Boston, and TV’s Entourage. What’s all the more irritating is that fans of both never could have envisioned the two ending so poorly after the way they started eight years ago.

Well, I didn’t think so. Then, it became so clear. The fate of one was almost directly linked to the performance of the other, and essentially worked that way all along.

I started thinking about this a few days ago, after last month’s dreadful series-finale of the HBO institution, followed a couple of weeks later by the collapse of the check-out-the-name-on-the-back-of-my-jersey Red Sox.

With curious storylines, it was obvious from the first episode of season eight that Entourage had a lot of work to do to avoid a bad year. It seemed like the group behind the show had spent more time promoting its final season than actually writing it.

When the Red Sox started their 2011 campaign just 2-10 after the prognosticators predicted the organization’s first 100-win season since 1946, it was curious how they’d right the ship. Even Francona couldn’t quite put his finger on it.

Watch: Francona Talks About Frustrations of 2011

Then, after that dreadful start, the Red Sox figured it out for a while. Enough individual talent can at times make up for a lack of overall chemistry.

With that same theory in mind, Entourage had its moments as well, but not many. Regardless, what happened in the middle didn’t matter. Both entities had to have a conclusion, and both were almost equally unbelievable.

This pattern, however, began long ago. In fact, if it was a movie trailer, it would go something like this:

Eight years ago…one man and one show burst onto the scene, completely independent of one another…Both rose to unimaginable fame, their popularity continuing to grow with each passing year…Suddenly, they peaked…The success was over, and the criticisms began until they had nothing left…Starring Terry Francona of the Red Sox and HBO’s Entourage…MIRROR IMAGES…Coming this fall.

For the record, I didn’t say it was a good movie trailer.

Let’s look at the facts, year-by-year, in a fashion that would make Ken Burns proud.

1st Inning – Why Should We Believe in This?

tito introduced Tito Could Have Predicted End with Red Sox By Watching Entourage

On December 4, 2003, the Boston Red Sox introduced Terry Francona as the 44th manager in team history. (Photo by Jessica Rinaldi/Getty Images)

In 2004, HBO took a chance on relatively unknown, largely unproven writer/producer Doug Ellin, who basically told them he wanted to make a show about a young A-list actor named Vincent Chase and his childhood buddies from Queens. The whole thing would be loosely based on executive producer Mark Wahlberg’s life as an up-and-coming film star. You know, before Mark was the funkiest of the bunch.

That same year, the Red Sox – with the package-like blessing of famed pitcher Curt Schilling – opened their arms and wallets to baseball lifer and flailing manager Terry Francona. Before coming to Boston, Francona’s only managerial experience came with Philadelphia, where he never had more than 75 wins, the Phillies never finished better than third-place and he had a career record of 285-363 from 1997-00. The Phillies for Francona were Ellin’s Life with Bonnie with Bonnie Hunt.

Don’t remember it? Bonnie Hunt barely remembers it.

2nd Inning – Unpredictable Success

Entourage’s first season was a mere eight episodes, but the critics couldn’t get enough of the brotherly bond of four men from New York, transplanted to Los Angeles as two Chase brothers chased Hollywood success. The crew included pretty boy Vinnie, his best friend Eric, their fat friend Turtle, Vinnie’s struggling-to-succeed brother Johnny Drama (played by Matt Dillon’s brother Kevin, who many would argue was playing himself at the time), and Ari Gold, the larger-than-life agent depicted so beautifully and vulgarly by Jeremy Piven, leading to the rebirth of his career. By the end of the season, Chase’s mainstream success with the movie Head On leads to indie project Queens Boulevard, “E” becomes Vinnie’s manager, Turtle does little more than chauffeur everyone around, and Kevin Dillon continues to wonder if he’s getting punk’d. In real life, viewers had never seen anything like it and the show received a Golden Globe nomination for Best Comedy Series.

2004 boston red sox Tito Could Have Predicted End with Red Sox By Watching Entourage

Francona said watching his players pile up on the field after their championship wins were his favorite moments. (Photo by Stephen Dunn/Getty Images)

Francona, we know what he did. Tito took the Sox – a group of self-proclaimed “Idiots” – to a 98-64 regular season record, a wild card berth for the second-best record in the AL behind those pains in the neck in the Bronx, the club flourished in the second-half and cruised to a three-game sweep of the Angels in the ALDS. After that, you’d think Hollywood took over. I mean, c’mon – Boston drops three to New York, only to reel off four wins starting from their final few outs in Game 4 against its biggest rival to advance to the World Series? There was no way the Sox would lose after that, not even the Red Sox. They swept St. Louis with ease for their first Series victory in 86 years, many people vowed they could die happy, several were likely…ummm…planned for on that very night, and Grady Little became nothing more than a horrible nightmare. Francona, not that he would have, could’ve walked away then and never bought another meal in New England again. Word is Dave Roberts still hasn’t thanks to that steal off Mo.

3rd Inning – Sure, We Partied, but the Hangover Isn’t Bad

Entourage kept rolling in 2005. Three Emmy nominations and a Golden Globe opportunity, thanks to stories around Aquaman, Vince’s obsession with wholesome ex Mandy Moore, and the drama between Ari and his partner Terrence McQuewick, who we’re later led to believe somehow spawned Sloan, played by the too-good-to-be-true Emmanuelle Chriqui. Oh, and Turtle becomes the manager of a rapper named Saigon, who actually managed to come out with a couple of albums thanks to the show. This was just one case of many where this show effectively reincarnated careers. Seriously, Jean-Claude Van Damme could have put a movie in theaters again with a guest spot.

Gallery: Terry Francona Through The Years

As for the Red Sox, Francona personally had a tough season, hospitalized for chest pains early in the year. Tests revealed he had clogged arteries, which in combination with past medical woes led to circulation issues. The pullover drama and rarely-to-be-seen-again uniform top story was born. On the field, though, his club won 95 games and advanced to the postseason for the third year in the row for the first time in franchise history, a team that came into existence in 1901, by the way. Sadly, they lost, swept in three games by the White Sox in the opening round. David Ortiz and Manny Ramirez did all they could for the offense, but the Sox started Matt Clement, David Wells and Tim Wakefield, all of whom had about as much success then as if they started this October.

4th Inning – The Divide

Entourage made a series season-high 20 episodes in 2006, was nominated for five more Emmy’s and two Golden Globe awards and the show even took home its first significant honor as Jeremy Piven received the Emmy for Outstanding Supporting Actor in a comedy. At that point, he was no longer known for being Dean Pritchard or John Cusack’s best friend. Frankly, he’ll always be Droz Andrews from PCU to me. As for what happened on the screen, Chase’s career hits a downward spiral when he gets fired by Warner Brothers, he then fires and rehires Ari, E thinks for some absurd reason that Sloan would have a threesome in spite of the fact he’s an Islanders fan, Drama yells “Victory” a lot, and we see a side of Beverly D’Angelo that we never saw in the National Lampoon flicks.

81923278 10 Tito Could Have Predicted End with Red Sox By Watching Entourage

Where's Manny? Just taking a drink inside the monster... (Photo by Elsa/Getty Images)

That’s our first and perhaps only break to the pattern, though, as Francona endured his first truly tough year in Boston, a season many around New England would prefer to forget and fans in Kansas City would probably covet. Think of it like Matt Damon making Daredevil rather than Ben Affleck. Matt just knows he can do better. Anyhow, Tito’s bunch had 86 wins, a third-place finish and a number of injuries to key personnel. Sure, Ortiz had a great season and Jonathan Papelbon was virtually unhittable, but Ramirez appeared in only 130 games, Josh Beckett was awful in his first year with the team, Clement was worse and Doug Mirabelli got police escorts all over town. There was also that 9-21 August record, including a five-game sweep at the hands of New York. That’s right, a sweep of three or four games wouldn’t have been bad enough, this club took its struggles to All About Steve levels.

5th Inning – It Doesn’t Get Any Better than This

2007 was a peak for Entourage in many ways. The series won two more Emmy’s (in seven chances) and a Golden Globe, and Piven took home one of each as he continued to bring his mom to the award shows year after year. As for the plot, Vinnie and Eric continue to clash professionally, which still worked for the show at the time, and we get to know Ari’s assistant Lloyd, creating a dynamic between the two that would eventually be one of the last routinely entertaining things on the show. E also struggles at expanding his management business as one star client does not make an agency, and Drama and Turtle, well, I don’t think I can really write about some of their plotlines. It was Cinemax After Dark type stuff. Vincent also sells his movie Medellin for a dollar, which had the fine-great-whatever feel of when Nomar signed with the Sox in 2010 just to retire with the club and make us forget the reasons he was traded in 2004 in the first place. We fans loved six of those nine seasons, though, Nomie! Big kiss, Mia!

As penned by Boston Herald columnist Steve Buckley, it was a Wicked Good Year for Boston. Other local success stories aside, Francona’s Sox treated 2006 like the series-finale to St. Elsewhere and posted the best record in the league, never relinquishing the AL East lead after April 18. That meant you could have done your taxes and checked back in while you planned ahead for Halloween and nothing would have changed. Long story short, 96 victories and another World Series win – this time over Colorado – marking the second in four years for a team that hadn’t enjoyed success like that since Woodrow Wilson was in office. It was wire-to-wire for this Sox team. The only thing Francona couldn’t do was quit the dip.

6th Inning – Nowhere to Go but Down

On the Entourage set, success continued but the award opportunities started to dwindle. Piven did grab his third Emmy in as many years, while the show received three more nominations. Among them, Dillon was pitted against Piven for the second year in a row. Drama’s drama had infatuated audiences, and he was a must-watch. It could be argued that he was the best character on the show (or a 1A, 1B situation with Ari Gold), plus he’d certainly regrouped professionally in real life to surpass brother Matt’s popularity. And, again, when this show started, Kevin Dillon was popular in the same way Billy Ripken or Brent Gretzky were household names. On the show, Medellin flopped but did earn more than a dollar, Vinnie pulled a Kenny Powers and went to Mexico for a little while to find himself, Drama breaks down on The View in a direct opposite to the way Tom Cruise jumped on Oprah’s couch, Ari basically kills a guy on a golf course, Turtle makes Jews world-wide jealous by dating Jamie-Lynn Sigler on the show and in real life, Vince gets and loses movie roles more frequently than Manny Ramirez jogged to first, and E starts the long process of becoming insufferable as a character.

Francona’s fifth season in Boston was memorable as well, but not always for the right reasons. His club won 95 games and came within a win of yet another World Series appearance (welcome to relevance, Tampa Bay), but he also had to deal with Ramirez, and the organization had finally had enough with Manny Being Manny. He was lazy on the base-paths, had a dugout scuffle with teammate Kevin Youkilis during a game and even shoved 64-year-old traveling secretary Jack McCormick over frustrations involving a ticket request. No word if he then brought his disdain for seniors to local old folk’s homes. Manny was traded, bound for LA, while Jason Bay came from Pittsburgh to take over left field. In the end, a premature exit for the Red Sox, but another good year for Francona.

7th Inning – Stretching Interest Just a Little Longer

Entourage received three Emmy nominations and three shots at a Golden Globe, but the show was done winning awards. Unfortunately, this season marked the beginning of the end as Ellin and his writers started focusing too much on individual storylines and not enough on the group. The sixth campaign watched Vince largely disappear into the background (not a complaint, by the way, as one of the show’s weaker actors), while E tries to make it on his own as a manager and dates a clingy hottie named Ashley before eventually getting engaged to Sloan. Turtle goes back to school, gets seduced by college co-eds and loses Jamie-Lynn (he did in real life as well), and Drama faces friction on the set of his hit show Five Towns. I’d need another column to breakdown everything that went on at the Miller-Gold Agency.

Back to baseball, 2009 brought another 95 wins and Francona’s final playoff appearance in Boston as his team was swept by the Angels – the Sox punching bags in the past – in the opening round. The team had six All-Stars and even won 11 straight games in April, but things went south after the July break and in the end the year proved to be just a season of regular season highs and postseason lows. Or, you might say, Saved by the Bell versus Saved by the Bell: The College Years.

8th Inning – Pink Hats Take Over

Watching Entourage in its seventh season was like singing “Sweet Caroline” at Fenway Park. It’s fashionable for casual fans, and the die-hards would walk away if not for that slim fear of missing something great. The show had only a couple of good episodes at best over the course of a 10-episode season, the award nominations were done and the plots started to reach for the sake of covering something that hadn’t been covered already.

Vince, who once pined over Mandy Moore’s candy, started dating and doing not-so-recreational drugs with porn star Sasha Grey. Grey attempted to make the move into mainstream media, just as her self-portrayed character tried to do on the show, and it just didn’t work out well for either of them. She may as well be dating Charlie Sheen now. The whole season was like watching Eminem during that period after he lost his best friend, Proof. You know, that whole Relapse era before Recovery when he was just too messed up to know what was good and what wasn’t. Ironically, the reformed Em makes a cameo in the season finale, only to punch out Vince – something viewers had wanted to do for years. It was a decent ending for a rough season, a year that also included Turtle’s foray into running a car service business and becoming a partner in a tequila company (how many different types of jobs are we supposed to believe this guy can have?), Ari’s lost shot at running an NFL team in LA, and Drama loses a part to Bob Saget, who was always laugh-out-loud funny in his guest spots. The table’s also set for Eric to split with Sloan while advancing his career.

Sound ridiculous? Wasn’t much better for the 2010 Red Sox. Francona’s bunch won 89 games and scored the fewest runs in a single-season since the Jimy Williams era. There’s a ton that could be written here, but all you really need to know is that general manager Theo Epstein referred to it as a “bridge year,” and that proved it would be as about exciting as it sounds. Eric Patterson appeared in 90 games and Daniel Nava, 60. Need I say more? I will. The season also marked the beginning of the John Lackey misery that has engulfed Fenway Park in a way like fans haven’t seen since Eric Gagne came out of the pen in 2007. I still can’t believe that guy got a championship ring. Anyhow, fact is, this team was riddled by injuries with 19 players spending 24 stints on the disabled list, and Jacoby Ellsbury, Dustin Pedroia and Kevin Youkilis all suffering season-ending injuries. A total of 53 players took the field for this team, including half the cast of Major League: Back to the Minors and two kids from Bad News Bears. Was it Francona’s toughest year, though? Not yet…

9th Inning – This? It Ended Like This?!

Was Entourage canceled? No. But nobody enjoyed the final season. The heavily promoted last installment was an embarrassment, right down to Jerry Ferrara (Turtle) getting his first crack as a script writer during the show’s send-off. The swan song lasted just eight episodes and ended with the happiest of happy endings. There wasn’t a single character who didn’t essentially find what he was looking for all along, which was completely, utterly unbelievable.

Vince sobered up, went on a great date with a journalist who spent half the season avoiding him and married her inside a couple of days. Eric spends the whole year having his existence cursed by Sloan, only to get back together with her and his unborn baby in the show’s final moments. Drama, aided by an amusing guest spot from Andrew Dice Clay, finds a great show and walks away from it, only to have it fall back in his lap. Plus, Vince writes/buys him a movie deal. Turtle, in one of the most absurd plots of the season, achieves his dream of bringing a New York City eatery to the west coast, and he’s able to fund it with money he didn’t know he had until the end, and he turns out to be a skinny multi-millionaire. As for Ari, he and his wife split, he dates an old flame who you felt throughout the series he’d rekindle something with eventually, and then gets back together with Mrs. Ari, before getting a movie cliff-hanger-like offer after the credits to return to LA once he’d quit the business. Everything other than Perrey Reeves in her sexy swimsuit made for a disaster of a series finale. Happy endings exist, but not everyone.

terryfranconahead Tito Could Have Predicted End with Red Sox By Watching Entourage

The times were tough and trying for Francona and the Red Sox in 2011. (Photo by J. Meric/Getty Images)

That’s what Terry Francona learned. Though his team won 90 games and led the American League standings for a good portion of the season, everything imploded, and in historic fashion. The Red Sox squandered a nine-game lead over the Rays, going 7-20 in September on the way to having a playoff berth stripped away in a span of about five horrifying minutes that even Wes Craven wouldn’t have penned. From Jonathan Papelbon being one strike away from forcing at least a one-game playoff with Tampa Bay for the wild card to Evan Longoria’s 13th inning walkoff home run against New York, Francona’s final experience managing Boston was what Entourage’s final season was – an embarrassment. This did not fall solely on Tito’s shoulders, of course. Like with Entourage, it took an ensemble cast of every man going his own way in the end. Sure, there were injuries, and lots of them. But that wasn’t the problem, at least not the identifying issue. Francona felt he’d lost control of an individually minded clubhouse, that his words had fallen on deaf ears, that he was no longer reaching men he’d gotten through to in the past, and so on. It was time, as he put it, for a “new voice” to take over, which only days ago led to what was billed as a mutual parting between he and the Red Sox when his two-year option was not picked up. Maybe it was mutual, maybe it wasn’t. It really doesn’t matter.

The Tenth Inning – The Big Picture

Ever since the first episode of Entourage in July of 2004, I was hooked. Sunday night meant HBO. If I missed the show, I caught the re-run the next day, but it was typically appointment viewing. In fact, about the only thing that would stand in my way was watching the Red Sox.

These were two of the only consistencies in a well-traveled life for the majority of the last decade, taking me from job to job in New York, Michigan, Virginia, Texas, Rhode Island and Massachusetts, not to mention a few pit-stops in between. Still, for the most part, wherever I was, on Sunday night there was Entourage. I’ve had a relationship with that show longer than my wife.

That said, if anyone associated with Entourage thinks the show went out on a high note, they’re crazy. Still, that shouldn’t diminish what it did during a lengthy and prominent prime. Generally, the critics loved the idea of a show that focused on the bond among bros and the feeling of family, equally important in baseball. The writing was smart, sharp, creative and often hilarious, but it ran its course after getting nominated for 25 Emmy’s in categories such as acting, directing and writing, plus 14 Golden Globe nominations. As noted earlier, there were a number of wins in the bunch, and that only includes the most high-ranking awards. Did we still care about these guys? Sure. But we were pretty sick of some of them a lot of the time as well.

My relationship with the Red Sox, meanwhile, started many, many years before Entourage, with my earliest memories coming from the disappointing, playoff-less teams of the early 1990’s. I don’t have to further detail how things have changed since. And, while that renaissance didn’t necessarily come directly because of Terry Francona, the results did largely occur once he was appointed manager – again, months before Entourage took to the airwaves.

Roche: Franchise At A Crossroads

The skipper leaves the Red Sox as the club’s second-winningest manager of all-time. He guided the Sox to two World Series titles, two pennants, five playoff appearances, a 744-552 regular season record and a 27-18 postseason mark, including a perfect 8-0 record on the biggest stage there is. I could sit here and rehash the numbers all day, but they’d only continue to show what we already know: The dude was good, Tom Hanks good. Including the playoffs, Francona averaged 96 wins a year, the same number of episodes Entourage lasted before calling it quits…until the movie is inevitably made.

Truth is, on both fronts, you could sort of see this coming. Eight years are a long time to do anything. Not many TV shows last that long, and neither do managers and coaches in any sport. The reason is, eventually people just get bored or tune out. On TV, when the character development is done and there are no stories of interest left to tell, dragging your feet before walking away will only get you cancelled, so why not walk away on top? Otherwise, it turns into All in the Family and gets renamed Archie Bunker’s Place. Nobody wants that. And nobody wanted Francona to stick around for another 10 years, potentially never winning it all again. You can be beloved, but that doesn’t mean a fresh face or new voice or temperament isn’t needed. Joe Torre won four World Series’ in his first five years in New York, and then stuck around another seven seasons. He left after 2007, and Joe Girardi won the crown two years later. Just one example. Plus, not even sabermetrics could identify the perfect TV show. There isn’t a one in history, I’d bet, that went out at just the right time and didn’t have any hiccups in between, and there will never be such a manager. The closest things might be Frasier (yes, really – 37 Emmy wins in 11 seasons – and that’s just the Emmys) and Red Auerbach (9 championships in 16 years coaching the Celtics).

From 2004 until 2011, in both sports and pop culture, we experienced two eight-year runs on two very different stages that endured the most similar of parallels, and neither Terry Francona’s managerial career with Boston nor Entourage’s success as a TV landmark will be tarnished by the way they ended. It’s like the natural progression of life – sitcoms and managing gigs begin and end and you hope you achieved all you could in between. If you get to go out on your own terms with your head held high, great, but most of us never see the end coming.

And yet, I can’t help but wonder if Francona watched that last episode of Entourage in early-September, when Boston still held a three-game lead on Tampa.

Adam Kaufman, a native of Massachusetts, joined the Sports Hub as an on-air personality in June 2011. He has worked as a television and radio anchor and broadcaster for various outlets since 2004, and his written views on sports and entertainment have appeared on NESN.com and in the New England Hockey Journal. You can follow him on Twitter @AdamMKaufman.
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