After standing pat in the offseason following their 2013 World Series championship and ultimately paying the price for it with a last place finish in 2014, the Boston Red Sox have opened up the checkbook and begun a frivolous free agency holiday shopping spree.

It’s just like in the winter of 2010 when Theo Epstein was still the general manager, and the Red Sox came to terms with Carl Crawford on that outrageous seven year, $142 million contract, and traded for Adrian Gonzalez, only to turn around and lock him up with a $154 million deal over seven years. Of course, they both turned out to be duds and key contributors to the September 2011 collapse that cost beloved Sox skipper Terry Francona his job, and were shipped out in a trade to the L.A. Dodgers in the midst of the disastrous 69 win campaign under Bobby Valentine the following season.

Four years later, it seems like the Sox have returned to throwing money at the big names on the market, but this time with Ben Cherington at the helm as the general manager, making a couple of his biggest moves (aside from the Gonzalez/Crawford/Josh Beckett trade to the Dodgers) since assuming the role as GM in the winter of 2011.

The troubled but talented Hanley Ramirez is headed to Boston. Yes, that Hanley Ramirez, the one who has been benched for his laziness and lack of hustle, the one who has missed 183 games over the last four seasons due to several different injuries, the one who will enter next season at 31 years-old, beginning a four year, $88 million contract with an option for a fifth year.

The Red Sox have also agreed to terms with three-time World Series champion and San Francisco fan favorite Pablo Sandoval to a five year deal, said to be in the range of $100 million with a club option for a sixth year.

Sandoval is probably not a $20 million player annually, but he would have received that type of contract regardless of what team he ended up signing with. While Sandoval did not receive much playing time in the 2010 Giants postseason run, he was a crucial part of the 2012 and 2014 World Series championships (he was crowned World Series MVP in 2012, and batted over .429 in this past Series). He’s a winner who takes it to another level when the stakes are high. While Sandoval has never had a 100 RBI season in his seven seasons in the big leagues, he has 20-25 home-run potential. A few decent years at third base should suffice, as all signs point towards Sandoval becoming David Ortiz’ successor as the designated hitter.

However, Ramirez is a huge gamble for the Red Sox, the team that tried to prove they were smarter than everyone else in the league by claiming to have devoted themselves to bringing in low-risk, ‘good character’ players that provide good chemistry.

The Red Sox thought they reinvented the wheel with the caution they displayed in the offseason that led to the miracle World Series title in 2013, so after making virtually no moves after the unexpected championship, the Sox managed to win just 71 games in 2014. Sure, a last place finish means it’s back to square one, but isn’t it a bit hypocritical of the Red Sox, the team so keen on chemistry and leadership the last two seasons, to overpay for a player with commitment issues? Ramirez obviously has the talent when his head is actually screwed on right, as a lifetime .300 hitter. He even has a career .356 postseason batting average. On the flip side, as a 31 year-old, he is on the wrong side of the prime of his career, and his selfish attitude has been (and will continue to be) unpopular with teammates (doesn’t he sound a lot like the last Ramirez that graced the grounds under the left field wall at Fenway?). If he can stay on the field, avoid the injuries, start hustling and have the desire to play night in and night out, there’s no reason he shouldn’t hit 30 homers and drive in 100 runs. For Boston’s sake, hopefully yet another change of scenery for Ramirez and the influence of Ortiz will straighten him out.

When the Red Sox lowballed their ace and postseason hero Jon Lester with a four year, $70 million deal this past April, didn’t that show they were unwilling to go long-term with players heading into their thirties?

This past April, BloombergBusinessweek profiled Red Sox principal owner John Henry, who was ecstatic about Martin Kleinbard’s study “Can’t Buy Much Love: Why Money Is Not Baseball’s Most Valuable Currency.”

“To me, the most important thing this study shows is that virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30,” Henry said. “Yet teams continue to extravagantly overpay for players above the age of 30.”

And extravagantly overpay they did, for Ramirez and Sandoval, who will be 35 and 34 respectively by the end of their new contracts. Tack on another year if the Sox decide to pick up the options at the tail ends of those contracts.

This offseason is far from over for the Sox. With an abundance of outfielders on the roster and a lack of starting pitching, there are still plenty of moves to be made.

If it is true that the Red Sox are planning on playing Ramirez in left field, then isn’t Yoenis Cespedes (who is set to earn $10.5 million in the final year of his current contract) a goner? If the Sox decide to go with Rusney Castillo in center field and use some sort of platoon with Mookie Betts, Shane Victorino and Allen Craig, then someone has to be the odd man out, right? Or, will the Sox stick with Cespedes in right field?

After trading Lester and John Lackey at the trade deadline last summer, the Red Sox were left with bleak starting pitching from top to bottom. If Boston was so willing to shell out $20 million annually to Ramirez and Sandoval this week, then they should show Lester the money, too. It would be a big blow to the Red Sox if Ramirez turns out to be a total dog and Lester decides to stick it to Boston and sign elsewhere.

The Sox ended last season without even having a left-handed pitcher in their starting rotation, so it makes all the sense in the world to bring back the familiar face in Lester, along with another legitimate arm to bolster the staff, whether through free agency or a trade.

It would be a big blow to Sox fans if the team with the highest ticket prices in baseball decided not to spend up to the luxury tax threshold of $189 million. But after the introductory press conferences for Ramirez and Sandoval on Tuesday, Henry told reporters that, “The way it’s structured we can blow through one year. Again for next year we have tremendous flexibility so we could go could through for one year and not overly effect us.”

Again, having to endure a long and boring 71 win, last place summer of baseball definitely warrants a shift in front office philosophies in order to get back to top. But it is pretty amusing that these blockbuster signings of Ramirez and Sandoval come only nine months after Red Sox president and CEO Larry Lucchino took a victory lap in response to the New York Yankees’ high spending, telling reporters, “We’re very different animals. I’m proud of that difference. I always cringe when people lump us together. Other baseball teams sometimes do that. They are still, this year at least, relying heavily on their inimitable old-fashioned Yankees style of high-priced, long-term free agents. And, uh, I can’t say that I wish them well, but I think that we’ve taken a different approach… If you compare what we did last year in the offseason to what they did this year, there’s quite a contrast there.” So have the Red Sox borrowed the “inimitable old-fashioned Yankees style” with the recent transactions? Hopefully Lucchino is ready to back off that stance a bit, with his team having just added an additional $41 million (and counting) to the payroll for next few years.

In the meantime, brace yourselves, Red Sox fans. This offseason has the potential to be one for the ages. If the Sox continue to wheel and deal, then hopefully we’ll be looking ahead to another fun summer of Red Sox baseball, not one where manager John Farrell has to deal with the challenge of filling out a lineup card full of minor leaguers.